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(3R,4S)-dihydroxy-5-oxohexylphosphonic acid + NADPH
? + NADP+
-
-
-
-
?
1,2-dideoxy-D-threo-3-hexulose 6-phosphate + NADPH + H+
2-C-ethyl-D-erythritol 4-phosphate + NADP+
-
i.e. 1-methyl-1-deoxy-D-xylulose 5-phosphate or M-DXP, a substrate analogue whichis inactive with the wild-type but active with mutant W204F
-
-
?
1-deoxy-D-xylulose 5-phosphate + NAD(P)H + H+
2-C-methyl-D-erythritol 4-phosphate + NAD(P)+
1-deoxy-D-xylulose 5-phosphate + NADPH
? + NADP+
-
-
-
-
?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
1-deoxy-D-xylulose-5-phosphate + NADH
methyl-D-erythritol-4-phosphate + NAD+
-
-
-
-
r
1-deoxy-D-xylulose-5-phosphate + NADPH
methyl-D-erythritol-4-phosphate + NADP+
1-deoxy-L-erythrulose + NADPH + H+
? + NADP+
-
reaction of the truncated substrate 1-deoxy-L-erythrulose in the presence and absence of phosphite dianion, overview
-
-
?
1-fluoro-1-deoxy-D-xylulose 5-phosphate + NADPH
?
1-fluoro-1-deoxy-D-xylulose-5-phosphate + NADPH
? + NADP+
-
-
-
-
?
2C-methyl-D-erythritol 4-phosphate + 2C-methyl-D-erythritol 4-phosphate + NADP+
? + NADPH
2C-methyl-D-erythritol 4-phosphate + hydroxyacetone + NADP+
? + NADPH
3-[2H]-D-1-deoxyxylulose-5-phosphate + NAD(P)H
? + NAD(P)+
-
-
-
-
?
4-[2H]-D-1-deoxyxylulose-5-phosphate + NAD(P)H
? + NAD(P)+
-
-
-
-
?
glycolaldehyde phosphate + hydroxyacetone + NADPH
? + NADP+
methyl-D-erythritol-4-phosphate + NADP+
1-deoxy-D-xylulose-5-phosphate + NADPH
-
-
-
-
r
additional information
?
-
1-deoxy-D-xylulose 5-phosphate + NAD(P)H + H+
2-C-methyl-D-erythritol 4-phosphate + NAD(P)+
the forward reaction is preferred
-
-
r
1-deoxy-D-xylulose 5-phosphate + NAD(P)H + H+
2-C-methyl-D-erythritol 4-phosphate + NAD(P)+
-
inverse secondary kinetic isotope effects for both 3-[2H] and 4-[2H]-D-1-deoxyxylulose-5-phosphate during DXR-catalyzed isomerization indicates that the enzyme operates through a retro-aldol/aldol mechanism
-
-
?
1-deoxy-D-xylulose 5-phosphate + NAD(P)H + H+
2-C-methyl-D-erythritol 4-phosphate + NAD(P)+
-
-
-
-
?
1-deoxy-D-xylulose 5-phosphate + NAD(P)H + H+
2-C-methyl-D-erythritol 4-phosphate + NAD(P)+
NADPH is the preferred cofactor
-
-
?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
-
-
?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
-
-
-
?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
second committed step in isopentenyl diphosphate biosynthesis via the plastidial nonmevalonate pathway of isoprenoid biosynthesis, overview
-
-
?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
second step of the deoxyxylulose 5-phosphate/methylerythritol 4-phosphate pathway with end product isopentenylphosphate
-
-
r
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
-
-
?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
-
-
-
?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
-
-
?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
-
-
-
?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
-
-
?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
-
-
-
?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
-
-
ir
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
-
-
ir
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
-
-
ir
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
-
-
ir
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
-
-
-
r
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
-
-
?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
-
-
-
?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
-
-
?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
-
-
-
?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
-
ir
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
involved in the biosynthesis of isopentenylphosphate
-
-
?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
key enzyme in the bacterial nonmevalonate pathway to terpenoids, DXR introduces the key branching structure required for the eventual production of isopentenyl diphosphate
-
-
?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
i.e. DXP
-
-
?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
i.e. DXP
-
-
r
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
-
-
-
?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
-
-
?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
-
-
?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
-
-
?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
the enzyme catalyzes the second committed step in the 2C-methyl-D-erythritol 4-phosphate pathway for biosynthesis of isopentenyl diphosphate
-
-
?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
-
-
?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
-
-
ir
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
-
-
ir
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
-
-
-
?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
-
-
?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
-
-
-
?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
-
-
?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
first committed step in the mevalonate-independent isopentenyl diphosphate biosynthetic pathway, overview
-
-
r
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
second step of the deoxyxylulose 5-phosphate/methylerythritol 4-phosphate pathway with end product isopentenylphosphate
-
-
?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
the forward direction is preferred
-
-
r
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
NADPH and 2-C-methyl-D-erythritol 4-phosphate bind to the free enzyme and the two bind together to generate a nonproductive ternary complex
-
-
?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
-
-
?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
first committed step in the mevalonate-independent isopentenyl diphosphate biosynthetic pathway, overview
-
-
r
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
the forward direction is preferred
-
-
r
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
-
-
-
?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
second step of the deoxyxylulose 5-phosphate/methylerythritol 4-phosphate pathway with end product isopentenylphosphate
-
-
?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
-
-
?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
-
-
?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
-
-
?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
-
-
?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
-
-
-
?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
-
-
ir
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
-
-
?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
-
-
-
?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
-
-
?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
-
-
-
?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
second step of the deoxyxylulose 5-phosphate/methylerythritol 4-phosphate pathway with end product isopentenylphosphate, overview
-
-
?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
the enzyme catalyzes the first committed step in the biosynthesis of isopentenyl diphosphate in the plastidial 2C-methyl-D-erythritol 4-phosphate pathway leading to production of forskolin, overview
-
-
?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
-
-
?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
-
-
ir
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
MH018577
-
-
-
?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
-
-
-
?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
second step of the methylerythritol 4-phosphate pathway
-
-
?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
step in the methylerythritol 4-phosphate pathway
-
-
?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
i.e. DXP
-
-
?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
-
-
-
?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
-
-
?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
-
-
?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
-
-
-
?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
-
-
?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
i.e. DXP
-
-
?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
-
-
?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
i.e. DXP
-
-
?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
-
-
?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
-
-
?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
-
-
?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
-
-
ir
1-deoxy-D-xylulose-5-phosphate + NADPH
methyl-D-erythritol-4-phosphate + NADP+
-
-
-
-
?
1-deoxy-D-xylulose-5-phosphate + NADPH
methyl-D-erythritol-4-phosphate + NADP+
-
-
-
-
r
1-deoxy-D-xylulose-5-phosphate + NADPH
methyl-D-erythritol-4-phosphate + NADP+
-
-
-
-
r
1-deoxy-D-xylulose-5-phosphate + NADPH
methyl-D-erythritol-4-phosphate + NADP+
-
-
-
-
?
1-fluoro-1-deoxy-D-xylulose 5-phosphate + NADPH
?
-
i.e. CF-DXP
-
-
?
1-fluoro-1-deoxy-D-xylulose 5-phosphate + NADPH
?
-
i.e. CF-DXP, results in about 25% of the activity with 1-deoxy-D-xylulose 5-phosphate
-
-
r
2C-methyl-D-erythritol 4-phosphate + 2C-methyl-D-erythritol 4-phosphate + NADP+
? + NADPH
-
in reaction mixtures containing 0.150.25 mM IspC from Escherichia coli, Mycobacterium tuberculosis or Arabidopsis thaliana, the reversible reaction can be followed over thousands of reaction cycles. No fragment exchange, and the frequency of exchange, if any, is less than 5 p.p.m. per catalytic cycle
-
-
r
2C-methyl-D-erythritol 4-phosphate + 2C-methyl-D-erythritol 4-phosphate + NADP+
? + NADPH
in reaction mixtures containing 0.15-0.25 mM IspC from Escherichia coli, Mycobacterium tuberculosis or Arabidopsis thaliana, the reversible reaction can be followed over thousands of reaction cycles. No fragment exchange, and the frequency of exchange, if any, is less than 5 p.p.m. per catalytic cycle
-
-
r
2C-methyl-D-erythritol 4-phosphate + 2C-methyl-D-erythritol 4-phosphate + NADP+
? + NADPH
-
in reaction mixtures containing 0.15-0.25 mM IspC from Escherichia coli, Mycobacterium tuberculosis or Arabidopsis thaliana, the reversible reaction can be followed over thousands of reaction cycles. No fragment exchange, and the frequency of exchange, if any, is less than 5 p.p.m. per catalytic cycle
-
-
r
2C-methyl-D-erythritol 4-phosphate + hydroxyacetone + NADP+
? + NADPH
-
reaction mixtures containing 0.23-0.25 mM IspC from Escherichia coli, Mycobacterium tuberculosis or Arabidopsis thaliana
-
-
?
2C-methyl-D-erythritol 4-phosphate + hydroxyacetone + NADP+
? + NADPH
reaction mixtures containing 0.23-0.25 mM IspC from Escherichia coli, Mycobacterium tuberculosis or Arabidopsis thaliana
-
-
?
2C-methyl-D-erythritol 4-phosphate + hydroxyacetone + NADP+
? + NADPH
-
reaction mixtures containing 0.23-0.25 mM IspC from Escherichia coli, Mycobacterium tuberculosis or Arabidopsis thaliana
-
-
?
glycolaldehyde phosphate + hydroxyacetone + NADPH
? + NADP+
-
reaction mixtures containing 0.21-0.34 mM IspC from Escherichia coli, Mycobacterium tuberculosis or Arabidopsis thaliana
-
-
?
glycolaldehyde phosphate + hydroxyacetone + NADPH
? + NADP+
reaction mixtures containing 0.21-0.34 mM IspC from Escherichia coli, Mycobacterium tuberculosis or Arabidopsis thaliana
-
-
?
glycolaldehyde phosphate + hydroxyacetone + NADPH
? + NADP+
-
reaction mixtures containing 0.21-0.34 mM IspC from Escherichia coli, Mycobacterium tuberculosis or Arabidopsis thaliana
-
-
?
additional information
?
-
participation in the control of the 2-C-methyl-D-erythritol 4-phosphate pathway
-
-
?
additional information
?
-
-
IspC does not catalyze the isomerisation of 1-deoxy-D-xylulose 5-phosphate to give 1-deoxy-L-ribulose 5-phosphate. Active site of IspC is located close to the surface, a flexible loop at the active site (amino acids 206216) is able to fold into at least three different conformations
-
-
?
additional information
?
-
-
used for the synthesis of [1-13C1]2C-methyl-D-erythritol 4-phosphate and [3-13C1]2C-methyl-D-erythritol 4-phosphate
-
-
?
additional information
?
-
-
reaction depends on NADPH although it does not involve a reduction step, putative aldehyde intermediate is converted to methyl-D-erythritol-4-phosphate in the presence of NADPH and to 1-deoxy-D-xylolose-5-phosphate in the presence of NADP+
-
-
?
additional information
?
-
-
1,1,1-trifluoro-1-deoxy-D-xylulose 5-phosphoric acid, 1,1-difluoro-1-deoxy-D-xylulose 5-phosphoric acid, and 1,2-dideoxy-D-hexulose 6-phosphate are poor substrates
-
-
?
additional information
?
-
IspC does not catalyze the isomerisation of 1-deoxy-D-xylulose 5-phosphate to give 1-deoxy-L-ribulose 5-phosphate. Active site of IspC is located close to the surface, a flexible loop at the active site (amino acids 206-216) is able to fold into at least three different conformations
-
-
?
additional information
?
-
-
IspC does not catalyze the isomerisation of 1-deoxy-D-xylulose 5-phosphate to give 1-deoxy-L-ribulose 5-phosphate. Active site of IspC is located close to the surface, a flexible loop at the active site (amino acids 206-216) is able to fold into at least three different conformations
-
-
?
additional information
?
-
C3-C4 substrate binding mode in which DXP chelates a DXR-bound divalent cation via its hydroxyl groups at C3 and C4. The conversion of 1-deoxy-D-xylulose 5-phosphate to 2-methyl-D-erythritol 4-phosphate max include a pseudo-single molecule transition state of the retro-aldol intermediates
-
-
?
additional information
?
-
-
C3-C4 substrate binding mode in which DXP chelates a DXR-bound divalent cation via its hydroxyl groups at C3 and C4. The conversion of 1-deoxy-D-xylulose 5-phosphate to 2-methyl-D-erythritol 4-phosphate max include a pseudo-single molecule transition state of the retro-aldol intermediates
-
-
?
additional information
?
-
C3-C4 substrate binding mode in which DXP chelates a DXR-bound divalent cation via its hydroxyl groups at C3 and C4. The conversion of 1-deoxy-D-xylulose 5-phosphate to 2-methyl-D-erythritol 4-phosphate max include a pseudo-single molecule transition state of the retro-aldol intermediates
-
-
?
additional information
?
-
-
DXR has rate-limiting roles in isopentenyl diphosphate and dimethylallyl diphosphate synthesis
-
-
?
additional information
?
-
-
IspC does not catalyze the isomerisation of 1-deoxy-D-xylulose 5-phosphate to give 1-deoxy-L-ribulose 5-phosphate. Active site of IspC is located close to the surface, a flexible loop at the active site (amino acids 206-216) is able to fold into at least three different conformations
-
-
?
additional information
?
-
-
development and evaluation of a high-throughput screening assay for simultaneous selection of inhibitors of the enzyme, overview
-
-
?
additional information
?
-
-
DXR is involved in the 2-C-methyl-D-erythritol 4-phosphate pathway
-
-
?
additional information
?
-
DXR is involved in the 2-C-methyl-D-erythritol 4-phosphate pathway
-
-
?
additional information
?
-
product identification by mass spectrometry (HPLC-MS)
-
-
-
additional information
?
-
-
product identification by mass spectrometry (HPLC-MS)
-
-
-
additional information
?
-
DXR can accelerate the biosynthesis of lycopene. DXR is an effective regulatory site for the synthesis and accumulation of diterpenoid compounds such as tanshinone
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additional information
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substrate synthesis and product identification method, overview
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additional information
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a retroaldol/aldol mechanism for the DXR catalyzed rearrangement of 1-deoxy-D-xylulose 5-phosphate to 2-C-methyl-D-erythritol 4-phosphate. DXR first cleaves the C3-C4 bond of 1-deoxy-D-xylulose 5-phosphate in a retroaldol manner to generate a three-carbon and a two-carbon phosphate bimolecular intermediate. These two species are then reunited by an aldol reaction to form a new C-C bond, yielding the same aldehyde intermediate methylerythrose phosphate. Subsequent reduction of methylerythrose phosphate by NADPH affords 2-C-methyl-D-erythritol 4-phosphate
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additional information
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mono-((2S,3S)-3-fluoromethyl-2,4-dihydroxy-3-methyl-butyl) ester is not a substrate for DXR
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additional information
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VvDxr residues S186, H209, S222, N227 and K228 may participate in binding of the DXP substrate's phosphate moiety. These residues are conserved. H209 is a part of a flexible loop (209-HPXWXMG-115) that closes on the active site upon substrate binding. While H209 interacts with the phosphate group, W211 and M213 shield the remaining part of Dxp from solvent
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additional information
?
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VvDxr residues S186, H209, S222, N227 and K228 may participate in binding of the DXP substrate's phosphate moiety. These residues are conserved. H209 is a part of a flexible loop (209-HPXWXMG-115) that closes on the active site upon substrate binding. While H209 interacts with the phosphate group, W211 and M213 shield the remaining part of Dxp from solvent
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additional information
?
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VvDxr residues S186, H209, S222, N227 and K228 may participate in binding of the DXP substrate's phosphate moiety. These residues are conserved. H209 is a part of a flexible loop (209-HPXWXMG-115) that closes on the active site upon substrate binding. While H209 interacts with the phosphate group, W211 and M213 shield the remaining part of Dxp from solvent
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1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
additional information
?
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participation in the control of the 2-C-methyl-D-erythritol 4-phosphate pathway
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1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
second committed step in isopentenyl diphosphate biosynthesis via the plastidial nonmevalonate pathway of isoprenoid biosynthesis, overview
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1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
second step of the deoxyxylulose 5-phosphate/methylerythritol 4-phosphate pathway with end product isopentenylphosphate
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r
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
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1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
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1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
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1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
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1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
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1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
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1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
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ir
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
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ir
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
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ir
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
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ir
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
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r
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
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1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
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1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
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ir
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
involved in the biosynthesis of isopentenylphosphate
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1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
key enzyme in the bacterial nonmevalonate pathway to terpenoids, DXR introduces the key branching structure required for the eventual production of isopentenyl diphosphate
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1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
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1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
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1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
the enzyme catalyzes the second committed step in the 2C-methyl-D-erythritol 4-phosphate pathway for biosynthesis of isopentenyl diphosphate
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1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
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ir
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
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ir
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
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1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
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?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
first committed step in the mevalonate-independent isopentenyl diphosphate biosynthetic pathway, overview
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r
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
second step of the deoxyxylulose 5-phosphate/methylerythritol 4-phosphate pathway with end product isopentenylphosphate
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1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
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?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
first committed step in the mevalonate-independent isopentenyl diphosphate biosynthetic pathway, overview
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r
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
second step of the deoxyxylulose 5-phosphate/methylerythritol 4-phosphate pathway with end product isopentenylphosphate
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?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
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?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
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?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
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?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
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?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
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ir
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
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?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
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?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
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1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
second step of the deoxyxylulose 5-phosphate/methylerythritol 4-phosphate pathway with end product isopentenylphosphate, overview
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1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
the enzyme catalyzes the first committed step in the biosynthesis of isopentenyl diphosphate in the plastidial 2C-methyl-D-erythritol 4-phosphate pathway leading to production of forskolin, overview
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1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
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1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
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ir
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
MH018577
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1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
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1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
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second step of the methylerythritol 4-phosphate pathway
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?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
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step in the methylerythritol 4-phosphate pathway
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?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
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?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
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?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
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?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
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?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
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?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
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?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
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?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
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ir
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
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(2-[[hydroxy(methyl)carbamoyl]oxy]ethyl)phosphonic acid
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(2R)-3-[4-(hydroxymethyl)-4-[[4-(hydroxymethyl)phenyl]methyl]piperidin-1-yl]propane-1,2-diol
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(2R)-3-[4-[2-[(cyclohexa-2,4-dien-1-yl)oxy]ethyl]-4-(hydroxymethyl)piperidin-1-yl]propane-1,2-diol
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(2R)-3-[[[1-butyl-2-(cyclobutylmethanesulfonyl)-1H-imidazol-5-yl]methyl](methyl)amino]propane-1,2-diol
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(2R,3R)-2,3,4-trihydroxybutyl dihydrogen phosphate
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IC50: 0.310 mM
(2R,3R)-4-amino-2,3-dihydroxybutyl dihydrogen phosphate
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very weak inhibitor, IC50: 5 mM, above
(2R,3S)-2,3-dihydroxy-4-(hydroxyamino)-4-oxobutyl dihydrogen phosphate
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very weak inhibitor, IC50: 5 mM, above
(2R,3S)-4-amino-2,3-dihydroxy-4-oxobutyl dihydrogen phosphate
-
IC50: 0.253 mM
(2S,3R)-2,3-dihydroxy-4-phosphonooxybutyric acid
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IC50: 0.551 mM
(2S,3R)-dihydroxybutyramide 4-phosphate
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50% inhibition at 0.09 mM
(2S,3R)-methyl 2,3-dihydroxy-4-phosphonooxybutyrate
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IC50: 1.024 mM
(3-(hydroxy[(pentafluorophenyl)carbonyl]amino)propyl)phosphonic acid
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(3-(N-hydroxyacetamido)-1-phenyl)propylphosphonic acid
92% inhibition at 0.1 mM
(3-acetamidopropyl)phosphonic acid
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(3-boronopropyl)phosphonic acid
MIC90 = 0.053 mg/ml
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(3-[hydroxy(5-oxohexanoyl)amino]propyl)phosphonic acid
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(3-[hydroxy(6-phenylhexanoyl)amino]propyl)phosphonic acid
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(3-[hydroxy(hexadecanoyl)amino]propyl)phosphonic acid
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(3R)-1-(2,2-dimethylpropyl)-3-hydroxy-3-([[(5-methyl-4H-1,2,4-triazol-3-yl)methyl]amino]methyl)piperidin-2-one
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(3S)-1-(cyclopropylmethyl)-3-([[(4,5-dimethyl-1,3-thiazol-2-yl)methyl]amino]methyl)-3-hydroxypiperidin-2-one
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(3S)-hydroxypentan-2-one 5-phosphate
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50% inhibition at 0.03 mM
(3S,4R)-3,4-dihydroxy-4-methyl-5-oxohexylphosphonic acid
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(3S,4R)-3-((2S)-1-(6,7-dimethoxy-4-(pyrrolidin-1-yl)-1,7,8,8a-tetrahydroquinazolin-2-yl)-4-hydroxybutan-2-yl)-4-hydroxytetrahydrothiophene 1,1-dioxide
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(4-chloro-2-[[1-(2,3-dihydroxypropyl)piperidin-4-yl]oxy]phenyl)(piperidin-1-yl)methanone
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(4-hydrazinyl-4-oxobutyl)phosphonic acid
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(4-[[3-(hydroxymethyl)phenyl]amino]-4-oxobutyl)phosphonic acid
(4S)-hydroxypentan-2-one 5-phosphate
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50% inhibition at 0.15 mM
(5R)-5-[1-[(2R)-2,3-dihydroxypropyl]piperidin-4-yl]-5-(3-phenylpropyl)imidazolidine-2,4-dione
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(pyridin-2-ylmethyl)phosphonic acid
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([[acetyl(hydroxy)amino]methoxy]methyl)phosphonic acid
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([[formyl(hydroxy)amino]methoxy]methyl)phosphonic acid
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1,1,1-trifluoro-1-deoxy-D-xylulose 5-phosphoric acid
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i.e. CF3-DXP, very low inhibition
1,1-difluoro-1-deoxy-D-xylulose 5-phosphoric acid
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i.e. CF2-DXP, very low inhibition
1,2-dideoxy-D-hexulose 6-phosphate
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i.e. Et-DXP, very low inhibition
1,2-dideoxy-D-threo-3-hexulose 6-phosphate
1,3,5-tris(4-hydroxyphenyl)-4-propyl-1H-pyrazole
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1-deoxy-D-xylulose 5-phosphate
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substrate inhibition
1-deoxy-L-ribulose 5-phosphate
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50% inhibition at 0.18 mM
1-hydroxy-5-phenylpyridin-2(1H)-one
1-[(2S)-2,3-dihydroxypropyl]-N-[3-(furan-2-yl)phenyl]piperidine-4-carboxamide
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13-methyl-[1,3]benzodioxolo[5,6-c]-1,3-dioxolo[4,5-i]phenanthridinium chloride
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2-[(5Z)-5-(3,4-dihydroxybenzylidene)-4-oxo-2-thioxo-1,3-thiazolidin-3-yl]-N-hydroxyacetamide
inhibitor keeps its inhibition capacity in the presence of Triton X-100 and shows antimicrobial activity against Escherichia coli
2-[acetyl(hydroxy)amino]ethyl phosphate
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2-[acetyl(methyl)amino]ethyl phosphate
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2-[formyl(hydroxy)amino]ethyl phosphate
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3'-[(8-cinnamoyl-5,7-dihydroxy-2,2-dimethyl-2H-1-benzopyran-6-yl)methyl]-2',4',6'-trihydroxy-5'-methylacetophenone
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3,3-dimethyl-11-phenyl-2,3,4,5,10,11-hexahydro-1H-dibenzo[b,e][1,4]diazepin-1-one
the inhibitor is believed to hamper the captivating step of the synthetic pathway, as a result of which inadequacy of IPP pool will definitely foster the endurance of parasite in the intraerythrocytic stage
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3-(3,5-dibromo-4-hydroxybenzylidine-5-iodo-1,3-dihydro-indol-2-one)
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3-(hydroxy([(2-phenylbutanoyl)amino]acetyl)amino)propylphosphonic acid
3-(hydroxy([(3-methylbutanoyl)amino]acetyl)amino)propylphosphonic acid
3-(hydroxy([(4-phenoxybutanoyl)amino]acetyl)amino)propylphosphonic acid
3-(hydroxy([(4-phenylbutanoyl)amino]acetyl)amino)propylphosphonic acid
3-(hydroxyamino)-3-oxopropyl phosphate
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3-(N-hydroxyacetamido)-1-(3,4-dichlorophenyl)propylphosphonic acid
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3-(N-hydroxyformamido)-1-(2-bromophenyl)propylphosphonic acid
93% inhibition at 0.1 mM
3-(N-hydroxyformamido)-1-(3,4-dichlorophenyl)propylphosphonic acid
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3-([(1H-indol-3-yl)acetyl]amino)propylphosphonic acid
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3-([2-(methoxycarbonyl)benzoyl]amino)propylphosphonic acid
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3-([3-(1H-indol-3-yl)propanoyl]amino)propylphosphonic acid
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3-([4-(1H-indol-3-yl)butanoyl]amino)propylphosphonic acid
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3-fluoro-1-deoxy-D-xylulose-5-phosphate
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noncompetitive
3-[(([(3,4-dimethoxyphenyl)acetyl]amino)acetyl)(hydroxy)amino]propylphosphonic acid
3-[(2-hydroxybenzoyl)amino]propylphosphonic acid
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3-[(3,4-diethoxybenzoyl)amino]propylphosphonic acid
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3-[(3,4-dimethoxybenzoyl)amino]propylphosphonic acid
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3-[(4-methylpentanoyl)amino]propylphosphonic acid
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3-[(4-phenoxybenzoyl)amino]propylphosphonic acid
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3-[([(cyclopropylcarbonyl)amino]acetyl)(hydroxy)amino]propylphosphonic acid
3-[hydroxy(([3-(trifluoromethoxy)benzoyl]amino)acetyl)amino]propylphosphonic acid
3-[hydroxy(([4-(1H-indol-3-yl)butanoyl]amino)acetyl)amino]propylphosphonic acid
3-[hydroxy(methyl)amino]-3-oxopropyl phosphate
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4-(1-(4-hydroxy-2-oxo-2H-chromen-3-yl)-2-methylpropyl)-5-methyl-2-(4-nitrophenyl)-1,2-dihydro-3H-pyrazol-3-one
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4-(N-formyl-N-hydroxy-amino)-butyric acid
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4-butyl-6-[4-([[(2R)-2,3-dihydroxypropyl](methyl)amino]methyl)phenyl]pyridin-2(1H)-one
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4-fluoro-1-deoxy-D-xylulose-5-phosphate
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noncompetitive
5-[hydroxy(methyl)amino]-5-oxopentanoic acid
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Arbutus andrachne plant extract
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carvacrol
55.6% inhibition of DXR
carveol
23.2% inhibition of DXR
Cercis siliquastrum leaf extract
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high inhibitory activity
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diethyl (1-(3,4-dichlorophenyl)-3-(N-hydroxyacetamido)propyl)phosphonate
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diethyl (1-(3,4-dichlorophenyl)-3-(N-hydroxyformamido)propyl)phosphonate
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diethyl (2-[[(furan-2-yl)methyl]amino]-2-oxoethyl)phosphonate
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diethyl (2-[[3-(hydroxymethyl)phenyl]amino]-2-oxoethyl)phosphonate
diethyl (3-[[3-(hydroxymethyl)phenyl]amino]-3-oxopropyl)phosphonate
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17.9% inhibition
diethyl [2-(3-hydroxyanilino)-2-oxoethyl]phosphonate
diethyl [2-oxo-2-[(1,3-thiazol-2-yl)amino]ethyl]phosphonate
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diethyl [2-oxo-2-[(pyridin-2-yl)amino]ethyl]phosphonate
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diethyl [2-[(3-bromophenyl)amino]-2-oxoethyl]phosphonate
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21.4% inhibition
diethyl [2-[(3-cyanophenyl)amino]-2-oxoethyl]phosphonate
diethyl [2-[(3-hydroxyphenyl)amino]-2-oxoethyl]phosphonate
diethyl [2-[(3-methoxyphenyl)amino]-2-oxoethyl]phosphonate
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11% inhibition
diethyl [2-[3-(hydroxymethyl)anilino]-2-oxoethyl]phosphonate
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diethyl [3-(3-hydroxyanilino)-3-oxopropyl]phosphonate
49.2% inhibition at 0.25 mM
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diethyl [3-[(3-hydroxyphenyl)amino]-3-oxopropyl]phosphonate
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33.5% inhibition
diethyl [3-[(3-methoxyphenyl)amino]-3-oxopropyl]phosphonate
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14.1% inhibition
diethyl [3-[3-(hydroxymethyl)anilino]-3-oxopropyl]phosphonate
17.9% inhibition at 0.25 mM
-
epigallocatechin gallate
specifically inhibits the enzyme and has antimicrobial activity, competitive inhibition versus DXP and uncompetitive inhibition versus NADPH
ethyl 1-[(2R)-2,3-dihydroxypropyl]-4-(2-phenoxyethyl)piperidine-4-carboxylate
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ethyl 1-[(2R)-2,3-dihydroxypropyl]-4-[[2-(trifluoromethyl)phenyl]methyl]piperidine-4-carboxylate
-
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ethyl 2-(2-ethoxy-2-oxoethyl)-2,5-dihydro-1H-benzo[b][1,4]diazepine-3-carboxylate
the inhibitor is believed to hamper the captivating step of the synthetic pathway, as a result of which inadequacy of IPP pool will definitely foster the endurance of parasite in the intraerythrocytic stage
-
ethyl hydrogen [1-(3,4-dichlorophenyl)-3-[formyl(hydroxy)amino]propyl]phosphonate
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ethyl hydrogen [3-[acetyl(hydroxy)amino]-1-(3,4-dichlorophenyl)propyl]phosphonate
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ethyl hydrogen [3-[acetyl(hydroxy)amino]-1-[2-(pyridin-3-yl)phenyl]propyl]phosphonate
20% inhibition at 0.1 mM
eugenol
68.3% inhibition of DXR
fosmidomycin analogues
synthesis, stereochemistry, and analysis of inhibitory potency of several fosmidomycin analogues, overview
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FR 900098
N-acetyl analogue of fosmidomycin
Geranium molle plant extract
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Helianthemum ventosum plant extract
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Helianthemum vesicarium plant extract
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linalool
22.7% inhibition of DXR
methyl N-([(3S)-1-[(2,3-difluorophenyl)methyl]-3-hydroxy-2-oxopiperidin-3-yl]methyl)glycinate
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N-hydroxy-N-[2-(3-hydroxy-3-oxido-3,4-dihydro-1H-2,3-benzoxaphosphinin-4-yl)ethyl]acetamide
12% inhibition at 0.1 mM
NaCl
-
100 mM, 87% residual activity
NADP+
-
product inhibition
phosphate mono-((2S,3S)-3-fluoromethyl-2,4-dihydroxy-3-methyl-butyl) ester
-
is a weak competitive inhibitor of DXR, most likely due to the steric hindrance caused by the substitution of a fluoromethylgroup for a hydroxyl group. Is not an irreversible inactivator (suicide inhibitor) for DXR, fails to act as a mechanism-based inactivator if the retroaldol/aldol mechanism is operative
phosphoric acid mono-[2-(N-acetyl-N-hydroxy-amino)-ethyl]-ester
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quercetin 3-beta-D-glucoside
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quercetin 3-D-galactoside
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Sarcopoterium spinosum plant extract
-
-
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sulfamic acid 2-(N-formyl-N-hydroxy-amino)-ethyl ester
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theaflavin-3'-gallate
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non-competitive against 1-deoxy-D-xylulose 5-phosphate and un-competitive inhibitors with respect to NADPH
theaflavin-3,3'-digallate
theaflavin-3-gallate
-
non-competitive against 1-deoxy-D-xylulose 5-phosphate and un-competitive inhibitors with respect to NADPH
Thymol
26.5% inhibition of DXR
[(1-isoquinolinylamino)methylene]-1,1-bisphosphonate
50% inhibition at 0.004 mM
[(3,4-dichlorophenyl)([2-[hydroxy(methyl)amino]-2-oxoethyl]sulfanyl)methyl]phosphonic acid
-
[(5-phenylpyridin-2-yl)methyl]phosphonic acid
[(5Z)-5-(3,4-dihydroxybenzylidene)-4-oxo-2-thioxo-1,3-thiazolidin-3-yl]acetic acid
inhibitor keeps its inhibition capacity in the presence of Triton X-100
[(quinolin-2-yl)methyl]phosphonic acid
-
-
[1,1'-biphenyl]-3,4-diol
-
-
[1-(3,4-dichlorophenyl)-3-[formyl(hydroxy)amino]propyl]phosphonic acid
[2-(1-hydroxy-6-oxo-1,6-dihydropyridin-2-yl)ethyl]phosphonic acid
-
-
[2-(2,3-dihydroxyphenyl)ethyl]phosphonic acid
-
-
[2-(3-hydroxy-4-methylphenyl)ethyl]phosphonic acid
-
-
[2-(3-methoxyanilino)-2-oxoethyl]phosphonic acid
17.8% inhibition at 0.25 mM
-
[2-([1-[(2R)-2,3-dihydroxypropyl]piperidin-4-yl]oxy)phenyl](piperidin-1-yl)methanone
-
-
[2-[(3-bromophenyl)amino]-2-oxoethyl]phosphonic acid
-
-
[2-[(3-cyanophenyl)amino]-2-oxoethyl]phosphonic acid
-
20.0% inhibition
[2-[(3-hydroxyphenyl)amino]-2-oxoethyl]phosphonic acid
[2-[(3-methoxyphenyl)amino]-2-oxoethyl]phosphonic acid
[2-[(hydroxycarbamoyl)oxy]ethyl]phosphonic acid
-
-
[2-[acetyl(hydroxy)amino]ethyl]phosphonic acid
74% inhibition at 0.1 mM
-
[3-(6-methyl-4,8-dioxo-1,3,6,2-dioxazaborocan-2-yl)propyl]phosphonic acid
MIC90 = 0.063 mg/ml
-
[3-(acetyl(hydroxy)amino)propyl]phosphonic acid 3-methylbutyl ester
-
[3-(acetyl(hydroxy)amino)propyl]phosphonic acid mono(2-naphthalen-1-yl-ethyl) ester
-
[3-(acetyl(hydroxy)amino)propyl]phosphonic acid mono(2-naphthalen-2-yl-ethyl) ester
-
[3-(acetyl(hydroxy)amino)propyl]phosphonic acid mono-n-butyl ester
-
[3-(acetyl(hydroxy)amino)propyl]phosphonic acid mono-n-propyl ester
-
[3-(acetyl(hydroxy)amino)propyl]phosphonic acid monomethyl ester
-
[3-(acetyl(hydroxy)amino)propyl]phosphonic acid monophenethyl ester
-
[3-(acetyl(hydroxy)amino)propyl]phosphonic monoethyl ester
-
[3-(N-acetyl-N-methyl-amino)propyl]-phosphonic acid
-
-
[3-(N-formyl-N-methyl-amino)-propyl]-phosphonic acid
-
-
[3-oxo-3-[(prop-2-yn-1-yl)amino]propyl]phosphonic acid
6.7% inhibition at 0.020 mM
-
[3-[acetyl(hydroxy)amino]-1-(1,4-dihydropyridin-4-yl)propyl]phosphonic acid
-
-
[3-[acetyl(hydroxy)amino]-1-(2-bromophenyl)propyl]phosphonic acid
38% inhibition at 0.1 mM
[3-[acetyl(hydroxy)amino]-1-(2-cyanophenyl)propyl]phosphonic acid
30% inhibition at 0.1 mM
[3-[acetyl(hydroxy)amino]-1-(2-methylphenyl)propyl]phosphonic acid
55% inhibition at 0.1 mM
[3-[acetyl(hydroxy)amino]-1-(3,4-dichlorophenyl)propyl]phosphonic acid
[3-[acetyl(hydroxy)amino]-1-(pyridin-3-yl)propyl]phosphonic acid
[3-[acetyl(hydroxy)amino]-1-(pyridin-4-yl)propyl]phosphonic acid
[3-[acetyl(hydroxy)amino]-1-phenylpropyl]phosphonic acid
[3-[acetyl(hydroxy)amino]-1-[2-(2-hydroxyethyl)phenyl]propyl]phosphonic acid
35% inhibition at 0.1 mM
[3-[acetyl(hydroxy)amino]-1-[2-(hydroxymethyl)phenyl]propyl]phosphonic acid
36% inhibition at 0.1 mM
[3-[acetyl(hydroxy)amino]-1-[2-(methoxymethyl)phenyl]propyl]phosphonic acid
30% inhibition at 0.1 mM
[3-[acetyl(hydroxy)amino]-1-[2-(pyridin-3-yl)phenyl]propyl]phosphonic acid
20% inhibition at 0.1 mM
[3-[acetyl(hydroxy)amino]-1-[2-(thiophen-2-yl)phenyl]propyl]phosphonic acid
30% inhibition at 0.1 mM
[3-[acetyl(naphthalen-2-ylmethoxy)amino]propyl]phosphonic acid
compound binds to both the NADPH and DXP sites, while whole-cell inhibitory activity is relatively poor
[3-[formyl(hydroxy)amino]-1-(pyridin-3-yl)propyl]phosphonic acid
[3-[formyl(hydroxy)amino]-1-(pyridin-4-yl)propyl]phosphonic acid
[3-[formyl(hydroxy)amino]-1-phenylpropyl]phosphonic acid
[3-[hydroxy(3-phenylpropanoyl)amino]propyl]phosphonic acid
-
compound binds to Dxr via a non-bisubstrate mechanism. The diethyl ester of [3-[hydroxy(3-phenylpropanoyl)amino]propyl]phosphonic acid inhibits Mycobacterium tuberculosis growth
[4-(2-acetylanilino)-4-oxobutyl]phosphonic acid
-
-
[4-(2-fluoroanilino)-4-oxobutyl]phosphonic acid
-
-
[4-(hydroxyamino)-4-oxobutyl]phosphonic acid
[4-(methoxyamino)-4-oxobutyl]phosphonic acid
-
-
[4-[(3-bromophenyl)amino]-4-oxobutyl]phosphonic acid
-
-
[4-[(3-hydroxyphenyl)amino]-4-oxobutyl]phosphonic acid
[4-[2-(methanesulfonyl)anilino]-4-oxobutyl]phosphonic acid
-
-
[4-[acetyl(hydroxy)amino]butyl]phosphonic acid
80% inhibition at 0.1 mM
-
[4-[hydroxy(methyl)amino]-4-oxobutyl]phosphonic acid
-
[4-[methoxy(methyl)amino]-4-oxobutyl]phosphonic acid
-
-
[5-[(3-bromophenyl)amino]-5-oxopentyl]phosphonic acid
-
26.8% inhibition
[[(5-chloro-2-pyridinyl)amino]methylene]-1,1-bisphosphonate
50% inhibition at 0.007 mM
[[(isoquinolin-1-yl)amino]methylene]bis(phosphonic acid)
-
-
(4-[[3-(hydroxymethyl)phenyl]amino]-4-oxobutyl)phosphonic acid
-
26.8% inhibition
(4-[[3-(hydroxymethyl)phenyl]amino]-4-oxobutyl)phosphonic acid
-
-
([[acetyl(hydroxy)amino]methoxy]methyl)phosphonic acid
-
-
([[acetyl(hydroxy)amino]methoxy]methyl)phosphonic acid
-
-
([[formyl(hydroxy)amino]methoxy]methyl)phosphonic acid
-
-
([[formyl(hydroxy)amino]methoxy]methyl)phosphonic acid
-
-
1,2-dideoxy-D-threo-3-hexulose 6-phosphate
-
50% inhibition at 0.63 mM
1,2-dideoxy-D-threo-3-hexulose 6-phosphate
-
weak, competitive inhibition, a highly conserved tryptophan residue in the flexible loop is blocked by the substrate analog
1,3,5-tris(4-hydroxyphenyl)-4-propyl-1H-pyrazole
i.e. PPT, lead molecule as inhibitor of IspC
-
1,3,5-tris(4-hydroxyphenyl)-4-propyl-1H-pyrazole
i.e. PPT, lead molecule as inhibitor of IspC
-
1,3,5-tris(4-hydroxyphenyl)-4-propyl-1H-pyrazole
i.e. PPT, lead molecule as inhibitor of IspC
-
1-hydroxy-5-phenylpyridin-2(1H)-one
-
minimal inhibitory concentration for growth 0.02 mM
1-hydroxy-5-phenylpyridin-2(1H)-one
-
minimal inhibitory concentration for growth 0.1 mM
1-hydroxy-5-phenylpyridin-2(1H)-one
-
1-hydroxy-5-phenylpyridin-2(1H)-one
-
minimal inhibitory concentration for growth 0.1 mM
1-hydroxy-5-phenylpyridin-2(1H)-one
-
minimal inhibitory concentration for growth 0.05 mM
1-hydroxy-5-phenylpyridin-2(1H)-one
-
-
13-methyl-[1,3]benzodioxolo[5,6-c]-1,3-dioxolo[4,5-i]phenanthridinium chloride
i.e. sanguinarine chloride, lead molecule as inhibitor of IspC
-
13-methyl-[1,3]benzodioxolo[5,6-c]-1,3-dioxolo[4,5-i]phenanthridinium chloride
i.e. sanguinarine chloride, lead molecule as inhibitor of IspC
-
13-methyl-[1,3]benzodioxolo[5,6-c]-1,3-dioxolo[4,5-i]phenanthridinium chloride
i.e. sanguinarine chloride, lead molecule as inhibitor of IspC
-
2-[acetyl(hydroxy)amino]ethyl phosphate
-
-
2-[acetyl(hydroxy)amino]ethyl phosphate
-
-
2-[acetyl(methyl)amino]ethyl phosphate
-
-
2-[acetyl(methyl)amino]ethyl phosphate
-
-
2-[formyl(hydroxy)amino]ethyl phosphate
-
-
2-[formyl(hydroxy)amino]ethyl phosphate
-
-
3'-[(8-cinnamoyl-5,7-dihydroxy-2,2-dimethyl-2H-1-benzopyran-6-yl)methyl]-2',4',6'-trihydroxy-5'-methylacetophenone
i.e. rottlerin, lead molecule as inhibitor of IspC
-
3'-[(8-cinnamoyl-5,7-dihydroxy-2,2-dimethyl-2H-1-benzopyran-6-yl)methyl]-2',4',6'-trihydroxy-5'-methylacetophenone
i.e. rottlerin, lead molecule as inhibitor of IspC
-
3'-[(8-cinnamoyl-5,7-dihydroxy-2,2-dimethyl-2H-1-benzopyran-6-yl)methyl]-2',4',6'-trihydroxy-5'-methylacetophenone
i.e. rottlerin, lead molecule as inhibitor of IspC
-
3-(3,5-dibromo-4-hydroxybenzylidine-5-iodo-1,3-dihydro-indol-2-one)
i.e. GW5074, lead molecule as inhibitor of IspC
-
3-(3,5-dibromo-4-hydroxybenzylidine-5-iodo-1,3-dihydro-indol-2-one)
i.e. GW5074, lead molecule as inhibitor of IspC
-
3-(3,5-dibromo-4-hydroxybenzylidine-5-iodo-1,3-dihydro-indol-2-one)
i.e. GW5074, lead molecule as inhibitor of IspC
-
3-(hydroxy([(2-phenylbutanoyl)amino]acetyl)amino)propylphosphonic acid
-
-
3-(hydroxy([(2-phenylbutanoyl)amino]acetyl)amino)propylphosphonic acid
-
-
3-(hydroxy([(3-methylbutanoyl)amino]acetyl)amino)propylphosphonic acid
-
-
3-(hydroxy([(3-methylbutanoyl)amino]acetyl)amino)propylphosphonic acid
-
-
3-(hydroxy([(4-phenoxybutanoyl)amino]acetyl)amino)propylphosphonic acid
-
-
3-(hydroxy([(4-phenoxybutanoyl)amino]acetyl)amino)propylphosphonic acid
-
-
3-(hydroxy([(4-phenylbutanoyl)amino]acetyl)amino)propylphosphonic acid
-
-
3-(hydroxy([(4-phenylbutanoyl)amino]acetyl)amino)propylphosphonic acid
-
-
3-(hydroxyamino)-3-oxopropyl phosphate
-
-
3-(hydroxyamino)-3-oxopropyl phosphate
-
-
3-[(([(3,4-dimethoxyphenyl)acetyl]amino)acetyl)(hydroxy)amino]propylphosphonic acid
-
-
3-[(([(3,4-dimethoxyphenyl)acetyl]amino)acetyl)(hydroxy)amino]propylphosphonic acid
-
-
3-[([(cyclopropylcarbonyl)amino]acetyl)(hydroxy)amino]propylphosphonic acid
-
-
3-[([(cyclopropylcarbonyl)amino]acetyl)(hydroxy)amino]propylphosphonic acid
-
-
3-[hydroxy(([3-(trifluoromethoxy)benzoyl]amino)acetyl)amino]propylphosphonic acid
-
-
3-[hydroxy(([3-(trifluoromethoxy)benzoyl]amino)acetyl)amino]propylphosphonic acid
-
-
3-[hydroxy(([4-(1H-indol-3-yl)butanoyl]amino)acetyl)amino]propylphosphonic acid
-
-
3-[hydroxy(([4-(1H-indol-3-yl)butanoyl]amino)acetyl)amino]propylphosphonic acid
-
-
3-[hydroxy(methyl)amino]-3-oxopropyl phosphate
-
-
3-[hydroxy(methyl)amino]-3-oxopropyl phosphate
-
-
4-benzylbenzene-1,2-diol
-
minimal inhibitory concentration for growth 0.2 mM
4-benzylbenzene-1,2-diol
-
minimal inhibitory concentration for growth 1 mM
4-benzylbenzene-1,2-diol
-
4-benzylbenzene-1,2-diol
-
minimal inhibitory concentration for growth 0.2 mM
4-benzylbenzene-1,2-diol
-
minimal inhibitory concentration for growth 0.2 mM
biphenyl-3,4-diol
-
minimal inhibitory concentration for growth 0.2 mM
biphenyl-3,4-diol
-
minimal inhibitory concentration for growth 0.5 mM
biphenyl-3,4-diol
-
minimal inhibitory concentration for growth 0.2 mM
biphenyl-3,4-diol
-
minimal inhibitory concentration for growth 0.2 mM
catechin
-
catechin
3.35% inhibition
diethyl (2-[[3-(hydroxymethyl)phenyl]amino]-2-oxoethyl)phosphonate
-
40.4% inhibition
diethyl (2-[[3-(hydroxymethyl)phenyl]amino]-2-oxoethyl)phosphonate
-
-
diethyl [2-(3-hydroxyanilino)-2-oxoethyl]phosphonate
43.9% inhibition at 0.25 mM
diethyl [2-(3-hydroxyanilino)-2-oxoethyl]phosphonate
45.2% inhibition at 0.25 mM
diethyl [2-[(3-cyanophenyl)amino]-2-oxoethyl]phosphonate
-
11.9% inhibition
diethyl [2-[(3-cyanophenyl)amino]-2-oxoethyl]phosphonate
-
-
diethyl [2-[(3-hydroxyphenyl)amino]-2-oxoethyl]phosphonate
-
24.4% inhibition
diethyl [2-[(3-hydroxyphenyl)amino]-2-oxoethyl]phosphonate
-
-
diethyl [2-[3-(hydroxymethyl)anilino]-2-oxoethyl]phosphonate
40.4% inhibition at 0.25 mM
-
diethyl [2-[3-(hydroxymethyl)anilino]-2-oxoethyl]phosphonate
40.7% inhibition at 0.25 mM
-
EDTA
-
-
EDTA
-
complete inhibition at 5 mM
Fe2+
-
-
fosfoxacin
-
fosfoxacin
-
phosphate analogue of fosmidomycin
fosmidomycin
-
fosmidomycin
50% inhibition at 0.0035 mM
fosmidomycin
model for tight-binding mode of inhibition
fosmidomycin
acts by binding strongly to DXR as a slow tight-binding inhibitor, inhibitor-enzyme interaction and structure analysis for design of inhibitors, possibly mimics a transition state in the reaction coordinate of the substrate, the initial rapid equilibrium is subject to negative cooperativity, overview
fosmidomycin
-
a phosphonic metabolite from Streptomyces rubellomurinus
fosmidomycin
-
a natural product isolated from Streptomyces lavendulae
fosmidomycin
a naturally occurring retrohydroxamate phosphonic acid. DXR-NADPH-fosmidomycin complex crystal structure analysis, the phosphonate group of the inhibitor is located in the phosphate binding cleft of the substrate DXP and is bound in a similar fashion as the phosphate group
fosmidomycin
a natural product, which forms a chelate with the active site divalent metal ion (Mg2+/Mn2+) through its hydroxamate metal-binding group. Competitive versus 1-deoxy-D-xylulose 5-phosphate, uncompetitive versus NADPH, strong inhibition
fosmidomycin
-
IC50: 310 nM for the forward reaction, 0.0027 mM for the reverse reaction, Gram positive bacteria, including Mycobacterium tuberculosis, are resistant against the antibiotic fosmidomycin, which is an inhibitor of the enzyme from most gram-negative bacteria and other organisms
fosmidomycin
a natural product, which forms a chelate with the active site divalent metal ion (Mg2+/Mn2+) through its hydroxamate metal-binding group. Competitive versus 1-deoxy-D-xylulose 5-phosphate, uncompetitive versus NADPH
fosmidomycin
a naturally occurring retrohydroxamate phosphonic acid. DXR-NADPH-fosmidomycin complex crystal structure analysis, the phosphonate group of the inhibitor is located in the phosphate binding cleft of the substrate DXP and is bound in a similar fashion as the phosphate group
fosmidomycin
a natural antibiotic from Streptomyces lavendulae, a specific, mixed type inhibitor, the N-formyl-N-hydroxy amino headgroup of fosmidomycin coordinates Mg2+ ion forming an octahedral complex with active site residues Asp157, Glu159, and Glu241 and a critical binding site water molecule, residue His219 is essential for placing fosmidomycin in the active site for optimal catalysis, mechanism, overview, NADPH has a vital role in tight binding of the inhibitor within the enzyme active site
fosmidomycin
analysis of parasite growth in infected cultured erythrocytes. 50% growth inhibition at about 301 nM
fosmidomycin
-
a natural product isolated from Streptomyces lavendulae
fosmidomycin
a natural product, which forms a chelate with the active site divalent metal ion (Mg2+/Mn2+) through its hydroxamate metal-binding group. Competitive versus 1-deoxy-D-xylulose 5-phosphate, uncompetitive versus NADPH. No or poor inhibition by diethyl [3-[3-(hydroxymethyl)anilino]-3-oxopropyl]phosphonate, diethyl [3-(3-hydroxyanilino)-3-oxopropyl]phosphonate, and [3-(3-methoxyanilino)-3-oxopropyl]phosphonic acid
fosmidomycin
the DXR inhibitor shows safety as well as efficacy against Plasmodium falciparum malaria in clinical trials
fosmidomycin
IC50: 450 nM, recombinant enzyme, inhibition of growth and forskolin production in vivo
fosmidomycin
-
potent inhibitor but with very short half-life in plasma and low oral availability
FR-900098
-
fosmidomycin homologue
FR-900098
a naturally occurring retrohydroxamate phosphonic acid, isolated from the filtrate of a Pseudomonas fluorescens PK-52 culture
FR-900098
-
fosmidomycin homologue
FR900098
-
specific inhibition
FR900098
N-acetyl homologue of fosmidomycin
FR900098
fosmidomycin homologue
FR900098
-
an acetyl analogue of fosmidomycin
FR900098
a naturally occurring retrohydroxamate phosphonic acid
FR900098
analysis of parasite growth in infected cultured erythrocytes. 50% growth inhibition at about 118 nM
FR900098
-
an acetyl analogue of fosmidomycin
FR900098
-
N-acetyl analogue of fosmidomycin
gallocatechin gallate
-
completely suppresses the activity of DXR at 100 microM, and shows around 50% DXR inhibition at 25 microM
gallocatechin gallate
specifically inhibits the enzyme and has antimicrobial activity, competitive inhibition versus DXP and uncompetitive inhibition versus NADPH
gallocatechin gallate
strong inhibition of DXR, isolated from Camellia sinenesis
quercetin
-
quercetin
95.17% inhibition
quercetin 3-beta-D-glucoside
-
-
quercetin 3-beta-D-glucoside
-
-
quercetin 3-beta-D-glucoside
23.75% inhibition
-
quercetin 3-D-galactoside
-
-
quercetin 3-D-galactoside
-
-
quercetin 3-D-galactoside
23.21% inhibition
-
quercitrin
-
quercitrin
21.79% inhibition
suramin hexasodium
-
-
theaflavin-3,3'-digallate
-
non-competitive against 1-deoxy-D-xylulose 5-phosphate and un-competitive inhibitors with respect to NADPH
theaflavin-3,3'-digallate
strong inhibition of DXR, isolated from Camellia sinenesis
[(3,4-dichlorophenyl)([2-[hydroxy(methyl)amino]-2-oxoethyl]sulfanyl)methyl]phosphonic acid
-
-
[(3,4-dichlorophenyl)([2-[hydroxy(methyl)amino]-2-oxoethyl]sulfanyl)methyl]phosphonic acid
-
-
[(3,4-dichlorophenyl)([2-[hydroxy(methyl)amino]-2-oxoethyl]sulfanyl)methyl]phosphonic acid
-
-
[(5-phenylpyridin-2-yl)methyl]phosphonic acid
-
[(5-phenylpyridin-2-yl)methyl]phosphonic acid
-
-
[1-(3,4-dichlorophenyl)-3-[formyl(hydroxy)amino]propyl]phosphonic acid
-
[1-(3,4-dichlorophenyl)-3-[formyl(hydroxy)amino]propyl]phosphonic acid
conformation of inhibitor within the MtDXR active site (PDB ID 2Y1D)
[1-(3,4-dichlorophenyl)-3-[formyl(hydroxy)amino]propyl]phosphonic acid
inhibition of strain D2d
[1-(3,4-dichlorophenyl)-3-[formyl(hydroxy)amino]propyl]phosphonic acid
-
-
[2-[(3-hydroxyphenyl)amino]-2-oxoethyl]phosphonic acid
-
43.9% inhibition
[2-[(3-hydroxyphenyl)amino]-2-oxoethyl]phosphonic acid
-
-
[2-[(3-methoxyphenyl)amino]-2-oxoethyl]phosphonic acid
-
17.8% inhibition
[2-[(3-methoxyphenyl)amino]-2-oxoethyl]phosphonic acid
-
-
[3-[acetyl(hydroxy)amino]-1-(3,4-dichlorophenyl)propyl]phosphonic acid
-
[3-[acetyl(hydroxy)amino]-1-(3,4-dichlorophenyl)propyl]phosphonic acid
inhibition of strain D2d
[3-[acetyl(hydroxy)amino]-1-(3,4-dichlorophenyl)propyl]phosphonic acid
-
-
[3-[acetyl(hydroxy)amino]-1-(pyridin-3-yl)propyl]phosphonic acid
-
-
[3-[acetyl(hydroxy)amino]-1-(pyridin-3-yl)propyl]phosphonic acid
-
[3-[acetyl(hydroxy)amino]-1-(pyridin-3-yl)propyl]phosphonic acid
-
-
[3-[acetyl(hydroxy)amino]-1-(pyridin-4-yl)propyl]phosphonic acid
-
-
[3-[acetyl(hydroxy)amino]-1-(pyridin-4-yl)propyl]phosphonic acid
-
[3-[acetyl(hydroxy)amino]-1-(pyridin-4-yl)propyl]phosphonic acid
-
-
[3-[acetyl(hydroxy)amino]-1-phenylpropyl]phosphonic acid
-
-
[3-[acetyl(hydroxy)amino]-1-phenylpropyl]phosphonic acid
-
[3-[formyl(hydroxy)amino]-1-(pyridin-3-yl)propyl]phosphonic acid
-
-
[3-[formyl(hydroxy)amino]-1-(pyridin-3-yl)propyl]phosphonic acid
-
[3-[formyl(hydroxy)amino]-1-(pyridin-3-yl)propyl]phosphonic acid
-
-
[3-[formyl(hydroxy)amino]-1-(pyridin-4-yl)propyl]phosphonic acid
-
-
[3-[formyl(hydroxy)amino]-1-(pyridin-4-yl)propyl]phosphonic acid
-
[3-[formyl(hydroxy)amino]-1-(pyridin-4-yl)propyl]phosphonic acid
-
-
[3-[formyl(hydroxy)amino]-1-phenylpropyl]phosphonic acid
-
-
[3-[formyl(hydroxy)amino]-1-phenylpropyl]phosphonic acid
-
[4-(hydroxyamino)-4-oxobutyl]phosphonic acid
-
[4-(hydroxyamino)-4-oxobutyl]phosphonic acid
-
[4-(hydroxyamino)-4-oxobutyl]phosphonic acid
-
-
[4-[(3-hydroxyphenyl)amino]-4-oxobutyl]phosphonic acid
-
49.2% inhibition
[4-[(3-hydroxyphenyl)amino]-4-oxobutyl]phosphonic acid
-
-
[4-[hydroxy(methyl)amino]-4-oxobutyl]phosphonic acid
-
-
[4-[hydroxy(methyl)amino]-4-oxobutyl]phosphonic acid
-
-
additional information
-
1,1,1-trifluoro-1-deoxy-D-xylulose 5-phosphoric acid, 1,1-difluoro-1-deoxy-D-xylulose 5-phosphoric acid, and 1,2-dideoxy-D-hexulose 6-phosphate are poor inhibitors, most likely because of the increase in steric bulk at C1
-
additional information
-
inhibitor design and synthesis, overview
-
additional information
neither the sulfone (N-hydroxy-N-[3-(alkylsulfonyl)propyl]acetamides) nor the sulfonamide derivatives (N-hydroxy-N-(3-sulfamoylpropyl) acetamide and N-hydroxy-N-(3-(N-alkylsulfamoyl)propyl)acetamide) of FR900098 display any significant inhibitory activity against DXR at a concentration of 0.03 mM. Importance of the negative charge for the binding of fosmidomycin-like inhibitors to DXR. Uncharged molecules are virtually inactive whereas derivatives that possess only one instead of two negative charges are markedly less active. It is possible to regain some of the activity that is lost by the reduction of the charge by occupation of hitherto unexploited areas of the enzyme
-
additional information
-
inhibitory potencies of a series of aryl- and heteroarylcarbamoylphosphonic acids, their diethyl esters and disodium salts as analogues of the potent DXR inhibitor fosmidomycin, effects of the carboxamide N-substituents and the length of the methylene linker, in silico docking studies, saturation transfer difference NMR spectroscopy and enzyme inhibition assays, overview. Molecular modelling and simulated docking studies. No or poor inhibition by diethyl (4-[[3-(hydroxymethyl)phenyl]amino]-4-oxobutyl)phosphonate, diethyl [5-[(3-hydroxyphenyl)amino]-5-oxopentyl]phosphonate, [3-[(3-hydroxyphenyl)amino]-3-oxopropyl]phosphonic acid, [5-[(3-bromophenyl)amino]-5-oxopentyl]phosphonic acid, diethyl [5-[(3-methoxyphenyl)amino]-5-oxopentyl]phosphonate, [4-[(3-methoxyphenyl)amino]-4-oxobutyl]phosphonic acid, [5-[(3-methoxyphenyl)amino]-5-oxopentyl]phosphonic acid, diethyl [4-[(3-bromophenyl)amino]-4-oxobutyl]phosphonate, [4-[(3-bromophenyl)amino]-4-oxobutyl]phosphonic acid, and [5-[(3-bromophenyl)amino]-5-oxopentyl]phosphonic acid
-
additional information
possible interactions between DXR and the catechine inhibitors are simulated via molecular docking simulation, detailed overview. Triton X-100 does not affect the inhibition of the enzyme by epigallocatechin gallate and gallocatechin gallate, but that by baicalein (positive control)
-
additional information
hydroxamate analogues of fosfoxacin, the phosphate homologue of fosmidomycin, as inhibitors of DXR, synthesis and activities, analysis of Escherichia coli strain XL-1 Blue cell growth inhibition, overview
-
additional information
non-hydroxamate inhibitors of 1-deoxy-D-xylulose 5-phosphate reductoisomerase (DXR), docking study, structure-activity analysis, overview. No inhibiton at 0.02 mM by [3-(3-methoxyanilino)-3-oxopropyl]phosphonic acid or [3-[benzyl(pyridin-2-yl)amino]-3-oxopropyl]phosphonic acid or [3-[benzyl(3-hydroxyphenyl)amino]-3-oxopropyl]phosphonic acid or [2-[(sulfanylcarbonothioyl)amino]ethyl]phosphonic acid or [3-[(sulfanylcarbonothioyl)amino]propyl]phosphonic acid or [3-(2,3-dihydroxyphenyl)propyl]phosphonic acid
-
additional information
determination of the antimicrobial activities of various essential oils against different microbials using 35 plant essential oils (EOs), which have long been recognized for their antimicrobial properties. Essential oils of Zanbthoxylum bungeanum (ZB), Schizonepetae tenuifoliae (ST), Thymus quinquecostatus (TQ), Origanum vulgare (OV), and Eugenia caryophyllata (EC) display weak to medium inhibitory activity against DXR, with IC50 values of 0.078 mg/ml, 0.065 mg/ml, 0.059 mg/ml, 0.048 mg/ml, and 0.037 mg/ml, respectively. Dry roots or dry fruits are used for extraction. Cercis siliquastrum leaf extract strongly inhibits enzyme DXR. No effect by 0.5% DMSO on enzyme activity
-
additional information
-
determination of the antimicrobial activities of various essential oils against different microbials using 35 plant essential oils (EOs), which have long been recognized for their antimicrobial properties. Essential oils of Zanbthoxylum bungeanum (ZB), Schizonepetae tenuifoliae (ST), Thymus quinquecostatus (TQ), Origanum vulgare (OV), and Eugenia caryophyllata (EC) display weak to medium inhibitory activity against DXR, with IC50 values of 0.078 mg/ml, 0.065 mg/ml, 0.059 mg/ml, 0.048 mg/ml, and 0.037 mg/ml, respectively. Dry roots or dry fruits are used for extraction. Cercis siliquastrum leaf extract strongly inhibits enzyme DXR. No effect by 0.5% DMSO on enzyme activity
-
additional information
the methyl erythritol phosphate (MEP) pathway represents an attractive series of targets for antibiotic design, considering each enzyme of the pathway is both essential and has no human homologues. MEP pathway inhibitors (collectively called MEPicides) are most often rationally designed on the fosmidomycin scaffold, balancing target specificity with bioavailability. Pilot scale high-throughput screening (HTS) campaign against the first and second committed steps in the pathway, catalyzed by DXP reductoisomerase (IspC) and MEP cytidylyltransferase (IspD), using compounds present in the commercially available LOPAC1280 library as well as in an in-house natural product extract library. Analysis of mechanism of inhibition, most compounds function through aggregation. The method is useful for quickly screening a chemical library, while effectively identifying false positive compounds associated with assay constraints and aggregation. Screening using Yersinia pestis subsp. A1122, Mycobacterium tuberculosis, and Francisella tularensis subsp. novicida strain Utah 112, overview. Inhibition is attenuated in the presence of Triton X-100 for all inhibitors except sanguinarine chloride and suramin hexasodium
-
additional information
-
no substrate inhibition by 2-C-methyl-D-erythritol 4-phosphate, NADPH or NADP+
-
additional information
-
development and evaluation of a high-throughput screening spectrometric assay, measuring Dxr activity of Dxr coupled with 1-deoxy-D-xylulose-5-phosphate synthase, Dxs, activity, for simultaneous selection of inhibitors of the enzyme, overview
-
additional information
design, synthesis, and X-ray crystallographic studies of alpha-aryl 3,4-dichlorophenyl-substituted fosmidomycin analogues as enzyme inhibitors. The introduction of a 3,4-dichlorophenyl group in the Calpha-position relative to the phosphonate group produces analogues that have a higher in vitro antimalarial activity than fosmidomycin
-
additional information
-
design, synthesis, and X-ray crystallographic studies of alpha-aryl 3,4-dichlorophenyl-substituted fosmidomycin analogues as enzyme inhibitors. The introduction of a 3,4-dichlorophenyl group in the Calpha-position relative to the phosphonate group produces analogues that have a higher in vitro antimalarial activity than fosmidomycin
-
additional information
-
use of the Dxr-fosmidomycin cocrystal structure to design bisubstrate ligands to bind to both the 1-deoxy-D-xylulose-5-phosphate and NADPH sites
-
additional information
the methyl erythritol phosphate (MEP) pathway represents an attractive series of targets for antibiotic design, considering each enzyme of the pathway is both essential and has no human homologues. MEP pathway inhibitors (collectively called MEPicides) are most often rationally designed on the fosmidomycin scaffold, balancing target specificity with bioavailability. Pilot scale high-throughput screening (HTS) campaign against the first and second committed steps in the pathway, catalyzed by DXP reductoisomerase (IspC) and MEP cytidylyltransferase (IspD), using compounds present in the commercially available LOPAC1280 library as well as in an in-house natural product extract library. Analysis of mechanism of inhibition, most compounds function through aggregation. The method is useful for quickly screening a chemical library, while effectively identifying false positive compounds associated with assay constraints and aggregation. Screening using Yersinia pestis subsp. A1122, Mycobacterium tuberculosis, and Francisella tularensis subsp. novicida strain Utah 112, overview. Inhibition is attenuated in the presence of Triton X-100 for all inhibitors except sanguinarine chloride and suramin hexasodium
-
additional information
non-hydroxamate inhibitors of 1-deoxy-D-xylulose 5-phosphate reductoisomerase (DXR), docking study, structure-activity analysis, overview
-
additional information
hydroxamate analogues of fosfoxacin, the phosphate homologue of fosmidomycin, as inhibitors of DXR, synthesis and activities, overview
-
additional information
design and development of inhibitors, structure and docking modeling, overview
-
additional information
-
design and development of inhibitors, structure and docking modeling, overview
-
additional information
pyridine-containing fosmidomycin derivative inhibitor design and development using quantitative structure?activity relationship and crystallographic studies, synthesis, overview
-
additional information
-
pyridine-containing fosmidomycin derivative inhibitor design and development using quantitative structure?activity relationship and crystallographic studies, synthesis, overview
-
additional information
-
inhibitory potencies of a series of aryl- and heteroarylcarbamoylphosphonic acids, their diethyl esters and disodium salts as analogues of the potent DXR inhibitor fosmidomycin, effects of the carboxamide N-substituents and the length of the methylene linker, in silico docking studies, saturation transfer difference NMR spectroscopy and enzyme inhibition assays, overview. Molecular modelling and simulated docking studies. No or poor inhibition by diethyl [3-[(3-hydroxyphenyl)amino]-3-oxopropyl]phosphonate, diethyl [2-[(3-methoxyphenyl)amino]-2-oxoethyl]phosphonate, diethyl [3-[(3-methoxyphenyl)amino]-3-oxopropyl]phosphonate, diethyl [2-[(3-bromophenyl)amino]-2-oxoethyl]phosphonate, diethyl (3-[[3-(hydroxymethyl)phenyl]amino]-3-oxopropyl)phosphonate, [4-[(3-methoxyphenyl)amino]-4-oxobutyl]phosphonic acid, and [2-[(3-cyanophenyl)amino]-2-oxoethyl]phosphonic acid
-
additional information
non-hydroxamate inhibitors of 1-deoxy-D-xylulose 5-phosphate reductoisomerase (DXR), docking study, structure-activity analysis, overview
-
additional information
in silico identification and biological evaluation of inhibitors targeting 1-deoxy-D-xylulose-5-phosphate reductoisomerase, structure-based computational approach and biological evaluation, docking and binding mode estimation and molecular dynamics simulation, overview. Inhibitor screening in different database sources such as ZINC, NCI, ChemDB, PubChem, and Drugbank
-
additional information
computational design of potent inhibitors for deoxyxylulose 5-phosphate reductoisomerase and prediction of pharmacokinetics and pharmacodynamics, active site binding, molecular docking, and complex-based pharmacophore modeling, binding structures, overview
-
additional information
-
computational design of potent inhibitors for deoxyxylulose 5-phosphate reductoisomerase and prediction of pharmacokinetics and pharmacodynamics, active site binding, molecular docking, and complex-based pharmacophore modeling, binding structures, overview
-
additional information
-
inhibitor design and synthesis, structure-activity relationship profile for the inhibition of TgDXR, overview
-
additional information
the methyl erythritol phosphate (MEP) pathway represents an attractive series of targets for antibiotic design, considering each enzyme of the pathway is both essential and has no human homologues. MEP pathway inhibitors (collectively called MEPicides) are most often rationally designed on the fosmidomycin scaffold, balancing target specificity with bioavailability. Pilot scale high-throughput screening (HTS) campaign against the first and second committed steps in the pathway, catalyzed by DXP reductoisomerase (IspC) and MEP cytidylyltransferase (IspD), using compounds present in the commercially available LOPAC1280 library as well as in an in-house natural product extract library. Analysis of mechanism of inhibition, most compounds function through aggregation. The method is useful for quickly screening a chemical library, while effectively identifying false positive compounds associated with assay constraints and aggregation. Screening using Yersinia pestis strain A1122, Mycobacterium tuberculosis, and Francisella tularensis subsp. novicida strain Utah 112, overview. Inhibition is attenuated in the presence of Triton X-100 for all inhibitors except sanguinarine chloride and suramin hexasodium
-
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0.69
(3R,4S)-dihydroxy-5-oxohexylphosphonic acid
-
-
1.3
1,2-dideoxy-D-threo-3-hexulose 6-phosphate
-
pH 7.8, 37°C, recombinant mutant W204F
0.0031 - 12
1-deoxy-D-xylulose 5-phosphate
0.004 - 0.24
1-deoxy-D-xylulose-5-phosphate
53
1-deoxy-L-erythrulose
-
pH 7.5, 25°C, recombinant enzyme in absence or presence of phosphite dianion
0.227
1-fluoro-1-deoxy-D-xylulose 5-phosphate
-
pH 7.6, 37°C, recombinant enzyme
0.1
1-fluoro-1-deoxy-D-xylulose-5-phosphate
-
-
0.084 - 0.972
2-C-methyl-D-erythritol 4-phosphate
0.00537
3-[2H]-D-1-deoxyxylulose-5-phosphate
-
-
0.00423
4-[2H]-D-1-deoxyxylulose-5-phosphate
-
-
0.042 - 0.294
methyl-D-erythritol-4-phosphate
additional information
additional information
-
0.0031
1-deoxy-D-xylulose 5-phosphate
-
-
0.0255
1-deoxy-D-xylulose 5-phosphate
-
pH 7.6, 30°C, recombinant enzyme
0.04
1-deoxy-D-xylulose 5-phosphate
pH 7.5, 50°C
0.045
1-deoxy-D-xylulose 5-phosphate
-
pH 7.6, 37°C, recombinant enzyme
0.0471
1-deoxy-D-xylulose 5-phosphate
-
pH 7.9, 30°C, recombinant His-tagged enzyme
0.05
1-deoxy-D-xylulose 5-phosphate
-
pH 7.6, 37°C, recombinant enzyme
0.06
1-deoxy-D-xylulose 5-phosphate
with 1 mM CoCl2
0.081
1-deoxy-D-xylulose 5-phosphate
-
pH 7.6, 37°C, recombinant His-tagged enzyme
0.099
1-deoxy-D-xylulose 5-phosphate
with 1 mM MgCl2
0.1037
1-deoxy-D-xylulose 5-phosphate
-
pH 7.8, 22°C
0.11
1-deoxy-D-xylulose 5-phosphate
pH 7.5, 85°C
0.115
1-deoxy-D-xylulose 5-phosphate
-
pH 7.5, 25°C, recombinant enzyme
0.132
1-deoxy-D-xylulose 5-phosphate
pH 8.0, 37°C, recombinant pseudomature enzyme
0.137
1-deoxy-D-xylulose 5-phosphate
wild-type, pH 7.5, 25°C
0.147
1-deoxy-D-xylulose 5-phosphate
pH 8.0, 37°C, recombinant enzyme
0.17
1-deoxy-D-xylulose 5-phosphate
-
pH 7.8, 37°C, recombinant wild-type enzyme
0.222
1-deoxy-D-xylulose 5-phosphate
pH 7.8, 37°C
0.25
1-deoxy-D-xylulose 5-phosphate
with 1 mM MnCl2
0.3
1-deoxy-D-xylulose 5-phosphate
-
-
0.34
1-deoxy-D-xylulose 5-phosphate
-
-
0.39
1-deoxy-D-xylulose 5-phosphate
mutant W203Y, pH 7.5, 25°C
0.42
1-deoxy-D-xylulose 5-phosphate
-
pH 7.8, 37°C, recombinant mutant W204F
1.015
1-deoxy-D-xylulose 5-phosphate
mutant W203F, pH 7.5, 25°C
2.9
1-deoxy-D-xylulose 5-phosphate
-
pH 7.8, 37°C, recombinant mutant W204L
5
1-deoxy-D-xylulose 5-phosphate
-
pH 7.8, 37°C, recombinant mutant W204V
12
1-deoxy-D-xylulose 5-phosphate
-
pH 7.8, 37°C, recombinant mutant W204A
0.004
1-deoxy-D-xylulose-5-phosphate
-
cosubstrate NADPH, presence of Co2+, pH 7.5, 25°C
0.042
1-deoxy-D-xylulose-5-phosphate
-
cosubstrate NADPH, presence of Mg2+, pH 7.5, 25°C
0.05
1-deoxy-D-xylulose-5-phosphate
-
cosubstrate NADH, presence of Co2+, pH 7.5, 25°C
0.061
1-deoxy-D-xylulose-5-phosphate
-
-
0.063
1-deoxy-D-xylulose-5-phosphate
-
pH 7.5, 37°C, presence of 1 mM Co2+
0.073
1-deoxy-D-xylulose-5-phosphate
-
pH 7.7, presence of 1 mM MnCl2
0.097
1-deoxy-D-xylulose-5-phosphate
-
pH 7.7, presence of 3 mM MgCl2
0.1
1-deoxy-D-xylulose-5-phosphate
-
cosubstrate NADPH, presence of Mn2+, pH 7.5, 25°C
0.134
1-deoxy-D-xylulose-5-phosphate
-
pH 7.5, 37°C, presence of 1 mM Mg2+
0.195
1-deoxy-D-xylulose-5-phosphate
-
pH 7.5, 37°C, presence of 1 mM Mn2+
0.21
1-deoxy-D-xylulose-5-phosphate
-
cosubstrate NADH, presence of Mg2+, pH 7.5, 25°C
0.24
1-deoxy-D-xylulose-5-phosphate
-
cosubstrate NADH, presence of Mn2+, pH 7.5, 25°C
0.084
2-C-methyl-D-erythritol 4-phosphate
-
pH 7.5, 25°C, recombinant enzyme
0.174
2-C-methyl-D-erythritol 4-phosphate
-
pH 7.9, 30°C, recombinant His-tagged enzyme
0.972
2-C-methyl-D-erythritol 4-phosphate
pH 8.0, 37°C, recombinant pseudomature enzyme
0.042
methyl-D-erythritol-4-phosphate
-
presence of Mg2+, pH 7.5, 25°C
0.158
methyl-D-erythritol-4-phosphate
-
pH 7.7, presence of 3 mM MgCl2
0.294
methyl-D-erythritol-4-phosphate
-
pH 7.7, presence of 1 mM MnCl2
0.05
NADH
-
presence of Co2+, pH 7.5, 25°C
0.26
NADH
-
presence of Mn2+, pH 7.5, 25°C
0.41
NADH
-
presence of Mg2+, pH 7.5, 25°C
0.17
NADP+
-
presence of Mg2+, pH 7.5, 25°C
0.42
NADP+
-
pH 7.5, 25°C, recombinant enzyme, with substrate 1-deoxy-D-xylulose 5-phosphate
0.47 - 1
NADP+
pH 8.0, 37°C, recombinant pseudomature enzyme
0.561
NADP+
-
pH 7.9, 30°C, recombinant His-tagged enzyme
0.0004
NADPH
-
presence of Co2+, pH 7.5, 25°C
0.0005
NADPH
-
pH 7.6, 37°C, recombinant enzyme
0.001
NADPH
-
pH 7.5, 37°C, presence of 1 mM Co2+
0.0028
NADPH
pH 7.5, 50°C
0.0033
NADPH
-
pH 7.5, 37°C, presence of 1 mM Mn2+
0.0033
NADPH
-
presence of Mn2+, pH 7.5, 25°C
0.005
NADPH
-
pH 7.5, 37°C, presence of 1 mM Mg2+
0.005
NADPH
-
presence of Mg2+, pH 7.5, 25°C
0.007
NADPH
with 1 mM MnCl2
0.009
NADPH
with 1 mM CoCl2
0.0098
NADPH
-
pH 7.5, 25°C, recombinant enzyme, with substrate 1-deoxy-D-xylulose 5-phosphate
0.01
NADPH
-
pH 7.5, 25°C, recombinant enzyme
0.0105
NADPH
pH 7.5, 85°C
0.0127
NADPH
pH 7.8, 37°C
0.0133
NADPH
-
pH 7.8, 22°C
0.02
NADPH
with 1 mM MgCl2
0.0297
NADPH
-
pH 7.9, 30°C, recombinant His-tagged enzyme
0.03
NADPH
pH 8.0, 37°C, recombinant pseudomature enzyme
0.0825
NADPH
pH 8.0, 37°C, recombinant enzyme
additional information
additional information
-
kinetics, recombinant His-tagged wild-type and mutant enzymes
-
additional information
additional information
-
steady-state and single-turnover kinetics, primary kinetic isotope effects, overview
-
additional information
additional information
-
transient kinetics and kinetic mechanism, stopped-flow fluorescence measurements, overview. Kinetics of pre-steady-state reactions and steady-state kinetics, comparison of simulated and experimental values, burst kinetics model for pre-steady-state kinetics
-
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6.5
(3-acetamidopropyl)phosphonic acid
pH and temperature not specified in the publication
-
0.0041
(pyridin-2-ylmethyl)phosphonic acid
-
pH 7.6, 30°C, recombinant enzyme
2
1,1,1-trifluoro-1-deoxy-D-xylulose 5-phosphoric acid
-
pH 7.6, 37°C, recombinant enzyme
3.4
1,1-difluoro-1-deoxy-D-xylulose 5-phosphoric acid
-
pH 7.6, 37°C, recombinant enzyme
6.2
1,2-dideoxy-D-hexulose 6-phosphate
-
pH 7.6, 37°C, recombinant enzyme
0.63
1,2-dideoxy-D-threo-3-hexulose 6-phosphate
-
pH 7.8, 37°C, recombinant wild-type enzyme
1.1
1-deoxy-D-xylulose 5-phosphate
-
pH 7.9, 30°C, recombinant His-tagged enzyme
0.0014 - 0.0256
1-hydroxy-5-phenylpyridin-2(1H)-one
0.444
3-fluoro-1-deoxy-D-xylulose-5-phosphate
-
-
0.24
4-(N-formyl-N-hydroxy-amino)-butyric acid
-
pH 7.5, 37°C
0.0224
4-benzylbenzene-1,2-diol
-
pH not specified in the publication, temperature not specified in the publication
0.733
4-fluoro-1-deoxy-D-xylulose-5-phosphate
-
-
0.0447
biphenyl-3,4-diol
-
pH not specified in the publication, temperature not specified in the publication
0.1483 - 0.1794
epigallocatechin gallate
0.000019
fosfoxacin
-
pH 7.5, 37°C
0.0000021 - 0.00097
fosmidomycin
0.000048 - 0.0009
FR900098
0.0234 - 0.0252
gallocatechin gallate
0.000002
phosphoric acid mono-[2-(N-acetyl-N-hydroxy-amino)-ethyl]-ester
-
pH 7.5, 37°C
2.8
sulfamic acid 2-(N-formyl-N-hydroxy-amino)-ethyl ester
-
pH 7.5, 37°C
0.0222 - 0.0224
theaflavin-3'-gallate
0.0133 - 0.0182
theaflavin-3,3'-digallate
0.0247 - 0.03
theaflavin-3-gallate
0.0021
[(5-phenylpyridin-2-yl)methyl]phosphonic acid
-
pH 7.6, 30°C, recombinant enzyme
0.000077
[1-(3,4-dichlorophenyl)-3-[formyl(hydroxy)amino]propyl]phosphonic acid
-
pH 7.6, 30°C, recombinant enzyme
3.6
[3-(N-acetyl-N-methyl-amino)propyl]-phosphonic acid
-
pH 7.5, 37°C
5
[3-(N-formyl-N-methyl-amino)-propyl]-phosphonic acid
-
pH 7.5, 37°C
0.00022
[3-[acetyl(hydroxy)amino]-1-(3,4-dichlorophenyl)propyl]phosphonic acid
-
pH 7.6, 30°C, recombinant enzyme
0.0000019 - 0.00097
[3-[acetyl(hydroxy)amino]-1-(pyridin-3-yl)propyl]phosphonic acid
0.000013 - 0.00053
[3-[acetyl(hydroxy)amino]-1-(pyridin-4-yl)propyl]phosphonic acid
0.000085 - 0.00093
[3-[acetyl(hydroxy)amino]-1-phenylpropyl]phosphonic acid
0.000013 - 0.000087
[3-[formyl(hydroxy)amino]-1-(pyridin-3-yl)propyl]phosphonic acid
0.0000089 - 0.000079
[3-[formyl(hydroxy)amino]-1-(pyridin-4-yl)propyl]phosphonic acid
0.00048 - 0.0015
[3-[formyl(hydroxy)amino]-1-phenylpropyl]phosphonic acid
2.4
[4-(hydroxyamino)-4-oxobutyl]phosphonic acid
-
pH 7.5, 37°C
additional information
additional information
inhibition kinetics
-
0.0014
1-hydroxy-5-phenylpyridin-2(1H)-one
-
pH not specified in the publication, temperature not specified in the publication
0.0256
1-hydroxy-5-phenylpyridin-2(1H)-one
-
pH 7.6, 30°C, recombinant enzyme
0.1483
epigallocatechin gallate
pH 7.0, 37°C, recombinant enzyme, competitive versus 1-deoxy-D-xylulose 5-phosphate
0.1794
epigallocatechin gallate
pH 7.0, 37°C, recombinant enzyme, uncompetitive versus NADPH
0.0000021
fosmidomycin
-
-
0.000014
fosmidomycin
mutant W203Y, pH 7.5, 25°C
0.000021
fosmidomycin
pH 7.5, 22°C
0.000034
fosmidomycin
-
pH 7.5, 22°C, IC50 versus proliferation of Plasmodium falciparum strain Dd2
0.000057
fosmidomycin
-
pH 7.5, 37°C
0.00006
fosmidomycin
mutant W203F, pH 7.5, 25°C
0.000085
fosmidomycin
pH 8.0, 37°C, recombinant pseudomature enzyme
0.00009
fosmidomycin
-
pH 7.6, 30°C, recombinant enzyme
0.000093
fosmidomycin
wild-type, pH 7.5, 25°C
0.0000989
fosmidomycin
-
pH 7.8, 22°C
0.00097
fosmidomycin
pH 7.8, 37°C
0.000048
FR900098
-
pH 7.6, 30°C, recombinant enzyme
0.00017
FR900098
pH 7.8, 37°C
0.0009
FR900098
-
pH 7.5, 37°C
0.0234
gallocatechin gallate
pH 7.0, 37°C, recombinant enzyme, uncompetitive versus NADPH
0.0252
gallocatechin gallate
pH 7.0, 37°C, recombinant enzyme, competitive versus 1-deoxy-D-xylulose 5-phosphate
0.0222
theaflavin-3'-gallate
-
substrate 1-deoxy-D-xylulose 5-phosphate, pH 7.4, 37°C
0.0224
theaflavin-3'-gallate
-
substrate NADPH, pH 7.4, 37°C
0.0133
theaflavin-3,3'-digallate
-
substrate 1-deoxy-D-xylulose 5-phosphate, pH 7.4, 37°C
0.0182
theaflavin-3,3'-digallate
-
substrate NADPH, pH 7.4, 37°C
0.0247
theaflavin-3-gallate
-
substrate NADPH, pH 7.4, 37°C
0.03
theaflavin-3-gallate
-
substrate 1-deoxy-D-xylulose 5-phosphate , pH 7.4, 37°C
0.0000019
[3-[acetyl(hydroxy)amino]-1-(pyridin-3-yl)propyl]phosphonic acid
pH 7.5, 22°C
0.000042
[3-[acetyl(hydroxy)amino]-1-(pyridin-3-yl)propyl]phosphonic acid
-
pH 7.5, 22°C, IC50 versus proliferation of Plasmodium falciparum strain Dd5
0.00097
[3-[acetyl(hydroxy)amino]-1-(pyridin-3-yl)propyl]phosphonic acid
-
pH 7.6, 30°C, recombinant enzyme
0.000013
[3-[acetyl(hydroxy)amino]-1-(pyridin-4-yl)propyl]phosphonic acid
pH 7.5, 22°C
0.000082
[3-[acetyl(hydroxy)amino]-1-(pyridin-4-yl)propyl]phosphonic acid
-
pH 7.5, 22°C, IC50 versus proliferation of Plasmodium falciparum strain Dd6
0.00053
[3-[acetyl(hydroxy)amino]-1-(pyridin-4-yl)propyl]phosphonic acid
-
pH 7.6, 30°C, recombinant enzyme
0.000085
[3-[acetyl(hydroxy)amino]-1-phenylpropyl]phosphonic acid
pH 7.5, 22°C
0.00093
[3-[acetyl(hydroxy)amino]-1-phenylpropyl]phosphonic acid
-
pH 7.5, 22°C, IC50 versus proliferation of Plasmodium falciparum strain Dd8
0.000013
[3-[formyl(hydroxy)amino]-1-(pyridin-3-yl)propyl]phosphonic acid
pH 7.5, 22°C
0.000055
[3-[formyl(hydroxy)amino]-1-(pyridin-3-yl)propyl]phosphonic acid
-
pH 7.6, 30°C, recombinant enzyme
0.000087
[3-[formyl(hydroxy)amino]-1-(pyridin-3-yl)propyl]phosphonic acid
-
pH 7.5, 22°C, IC50 versus proliferation of Plasmodium falciparum strain Dd3
0.0000089
[3-[formyl(hydroxy)amino]-1-(pyridin-4-yl)propyl]phosphonic acid
pH 7.5, 22°C
0.000035
[3-[formyl(hydroxy)amino]-1-(pyridin-4-yl)propyl]phosphonic acid
-
pH 7.5, 22°C, IC50 versus proliferation of Plasmodium falciparum strain Dd4
0.000079
[3-[formyl(hydroxy)amino]-1-(pyridin-4-yl)propyl]phosphonic acid
-
pH 7.6, 30°C, recombinant enzyme
0.00048
[3-[formyl(hydroxy)amino]-1-phenylpropyl]phosphonic acid
pH 7.5, 22°C
0.0015
[3-[formyl(hydroxy)amino]-1-phenylpropyl]phosphonic acid
-
pH 7.5, 22°C, IC50 versus proliferation of Plasmodium falciparum strain Dd7
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0.003
(2-[[hydroxy(methyl)carbamoyl]oxy]ethyl)phosphonic acid
Escherichia coli
above, pH and temperature not specified in the publication
-
0.31
(2R,3R)-2,3,4-trihydroxybutyl dihydrogen phosphate
Escherichia coli
-
IC50: 0.310 mM
5
(2R,3R)-4-amino-2,3-dihydroxybutyl dihydrogen phosphate
Escherichia coli
-
very weak inhibitor, IC50: 5 mM, above
5
(2R,3S)-2,3-dihydroxy-4-(hydroxyamino)-4-oxobutyl dihydrogen phosphate
Escherichia coli
-
very weak inhibitor, IC50: 5 mM, above
0.253
(2R,3S)-4-amino-2,3-dihydroxy-4-oxobutyl dihydrogen phosphate
Escherichia coli
-
IC50: 0.253 mM
0.551
(2S,3R)-2,3-dihydroxy-4-phosphonooxybutyric acid
Escherichia coli
-
IC50: 0.551 mM
1.024
(2S,3R)-methyl 2,3-dihydroxy-4-phosphonooxybutyrate
Escherichia coli
-
IC50: 1.024 mM
0.0013
(3-(hydroxy[(pentafluorophenyl)carbonyl]amino)propyl)phosphonic acid
Escherichia coli
pH 7.5, 30°C
0.0074
(3-(N-hydroxyacetamido)-1-phenyl)propylphosphonic acid
Mycobacterium tuberculosis
pH 7,5, 22°C
0.0054
(3-[hydroxy(5-oxohexanoyl)amino]propyl)phosphonic acid
Escherichia coli
pH 7.5, 30°C
0.0051
(3-[hydroxy(6-phenylhexanoyl)amino]propyl)phosphonic acid
Escherichia coli
pH 7.5, 30°C
0.0056
(3-[hydroxy(hexadecanoyl)amino]propyl)phosphonic acid
Escherichia coli
pH 7.5, 30°C
0.03
(3S,4R)-3,4-dihydroxy-4-methyl-5-oxohexylphosphonic acid
Escherichia coli
-
-
1
(4-hydrazinyl-4-oxobutyl)phosphonic acid
Escherichia coli
pH and temperature not specified in the publication
-
0.000087 - 0.00036
([[acetyl(hydroxy)amino]methoxy]methyl)phosphonic acid
-
0.0011 - 0.0049
([[formyl(hydroxy)amino]methoxy]methyl)phosphonic acid
-
0.0014
1-hydroxy-5-phenylpyridin-2(1H)-one
Escherichia coli
pH and temperature not specified in the publication
0.0038 - 0.0061
2-[(5Z)-5-(3,4-dihydroxybenzylidene)-4-oxo-2-thioxo-1,3-thiazolidin-3-yl]-N-hydroxyacetamide
0.000077 - 0.000279
2-[acetyl(hydroxy)amino]ethyl phosphate
-
0.000077 - 0.000279
2-[acetyl(methyl)amino]ethyl phosphate
-
0.000342 - 0.0021
2-[formyl(hydroxy)amino]ethyl phosphate
-
0.00312 - 0.125
3,3-dimethyl-11-phenyl-2,3,4,5,10,11-hexahydro-1H-dibenzo[b,e][1,4]diazepin-1-one
-
0.0093 - 0.02
3-(hydroxy([(2-phenylbutanoyl)amino]acetyl)amino)propylphosphonic acid
0.0096 - 0.012
3-(hydroxy([(3-methylbutanoyl)amino]acetyl)amino)propylphosphonic acid
0.0004 - 0.001
3-(hydroxy([(4-phenoxybutanoyl)amino]acetyl)amino)propylphosphonic acid
0.019 - 0.02
3-(hydroxy([(4-phenylbutanoyl)amino]acetyl)amino)propylphosphonic acid
0.0026 - 0.0092
3-(hydroxyamino)-3-oxopropyl phosphate
-
0.0007
3-(N-hydroxyacetamido)-1-(3,4-dichlorophenyl)propylphosphonic acid
Mycobacterium tuberculosis
pH 7,5, 22°C
0.0056
3-(N-hydroxyformamido)-1-(2-bromophenyl)propylphosphonic acid
Mycobacterium tuberculosis
pH 7,5, 22°C
0.00015
3-(N-hydroxyformamido)-1-(3,4-dichlorophenyl)propylphosphonic acid
Mycobacterium tuberculosis
pH 7,5, 22°C
0.03
3-([(1H-indol-3-yl)acetyl]amino)propylphosphonic acid
Escherichia coli
-
-
0.03
3-([2-(methoxycarbonyl)benzoyl]amino)propylphosphonic acid
Escherichia coli
-
-
0.03
3-([3-(1H-indol-3-yl)propanoyl]amino)propylphosphonic acid
Escherichia coli
-
-
0.03
3-([4-(1H-indol-3-yl)butanoyl]amino)propylphosphonic acid
Escherichia coli
-
-
0.012 - 0.014
3-[(([(3,4-dimethoxyphenyl)acetyl]amino)acetyl)(hydroxy)amino]propylphosphonic acid
0.03
3-[(2-hydroxybenzoyl)amino]propylphosphonic acid
Escherichia coli
-
-
0.03
3-[(3,4-diethoxybenzoyl)amino]propylphosphonic acid
Escherichia coli
-
-
0.03
3-[(3,4-dimethoxybenzoyl)amino]propylphosphonic acid
Escherichia coli
-
-
0.03
3-[(4-methylpentanoyl)amino]propylphosphonic acid
Escherichia coli
-
-
0.03
3-[(4-phenoxybenzoyl)amino]propylphosphonic acid
Escherichia coli
-
-
0.0033 - 0.0071
3-[([(cyclopropylcarbonyl)amino]acetyl)(hydroxy)amino]propylphosphonic acid
0.0029 - 0.0051
3-[hydroxy(([3-(trifluoromethoxy)benzoyl]amino)acetyl)amino]propylphosphonic acid
0.0066 - 0.017
3-[hydroxy(([4-(1H-indol-3-yl)butanoyl]amino)acetyl)amino]propylphosphonic acid
0.000046 - 0.000233
3-[hydroxy(methyl)amino]-3-oxopropyl phosphate
-
0.1
4-(1-(4-hydroxy-2-oxo-2H-chromen-3-yl)-2-methylpropyl)-5-methyl-2-(4-nitrophenyl)-1,2-dihydro-3H-pyrazol-3-one
Plasmodium falciparum
pH 7.5, 22°C
-
0.0224
4-benzylbenzene-1,2-diol
Escherichia coli
pH and temperature not specified in the publication
0.025
5-[hydroxy(methyl)amino]-5-oxopentanoic acid
Escherichia coli
pH and temperature not specified in the publication
-
0.1
diethyl (1-(3,4-dichlorophenyl)-3-(N-hydroxyacetamido)propyl)phosphonate
Mycobacterium tuberculosis
above, pH 7,5, 22°C
0.1
diethyl (1-(3,4-dichlorophenyl)-3-(N-hydroxyformamido)propyl)phosphonate
Mycobacterium tuberculosis
above, pH 7,5, 22°C
0.408
diethyl (2-[[(furan-2-yl)methyl]amino]-2-oxoethyl)phosphonate
Escherichia coli
pH and temperature not specified in the publication
-
0.73
diethyl [2-oxo-2-[(1,3-thiazol-2-yl)amino]ethyl]phosphonate
Escherichia coli
pH and temperature not specified in the publication
-
0.472
diethyl [2-oxo-2-[(pyridin-2-yl)amino]ethyl]phosphonate
Escherichia coli
pH and temperature not specified in the publication
-
0.2098
epigallocatechin gallate
Escherichia coli
pH 7.0, 37°C, recombinant enzyme
0.04 - 0.125
ethyl 2-(2-ethoxy-2-oxoethyl)-2,5-dihydro-1H-benzo[b][1,4]diazepine-3-carboxylate
-
0.038
ethyl hydrogen [1-(3,4-dichlorophenyl)-3-[formyl(hydroxy)amino]propyl]phosphonate
Mycobacterium tuberculosis
pH 7,5, 22°C
0.022
ethyl hydrogen [3-[acetyl(hydroxy)amino]-1-(3,4-dichlorophenyl)propyl]phosphonate
Mycobacterium tuberculosis
pH 7,5, 22°C
0.000342 - 0.0021
fosfoxacin
0.000008 - 107
fosmidomycin
0.000018 - 0.00032
FR-900098
0.000004 - 0.118
FR900098
0.0275
gallocatechin gallate
Escherichia coli
pH 7.0, 37°C, recombinant enzyme
0.0000045 - 0.0000092
[(3,4-dichlorophenyl)([2-[hydroxy(methyl)amino]-2-oxoethyl]sulfanyl)methyl]phosphonic acid
-
0.00084
[(5-phenylpyridin-2-yl)methyl]phosphonic acid
Escherichia coli
pH and temperature not specified in the publication
0.0031 - 0.0044
[(5Z)-5-(3,4-dihydroxybenzylidene)-4-oxo-2-thioxo-1,3-thiazolidin-3-yl]acetic acid
0.0159
[(quinolin-2-yl)methyl]phosphonic acid
Escherichia coli
pH and temperature not specified in the publication
-
0.0447
[1,1'-biphenyl]-3,4-diol
Escherichia coli
pH and temperature not specified in the publication
-
0.000028 - 0.000059
[1-(3,4-dichlorophenyl)-3-[formyl(hydroxy)amino]propyl]phosphonic acid
0.053
[2-(1-hydroxy-6-oxo-1,6-dihydropyridin-2-yl)ethyl]phosphonic acid
Mycobacterium tuberculosis
pH and temperature not specified in the publication
-
1.2
[2-(2,3-dihydroxyphenyl)ethyl]phosphonic acid
Escherichia coli
pH and temperature not specified in the publication
-
0.041
[2-(3-hydroxy-4-methylphenyl)ethyl]phosphonic acid
Mycobacterium tuberculosis
pH and temperature not specified in the publication
-
0.003
[2-[(hydroxycarbamoyl)oxy]ethyl]phosphonic acid
Escherichia coli
above, pH and temperature not specified in the publication
-
0.0021
[3-(acetyl(hydroxy)amino)propyl]phosphonic acid 3-methylbutyl ester
Escherichia coli
at 0.03 mM
0.0024
[3-(acetyl(hydroxy)amino)propyl]phosphonic acid mono(2-naphthalen-1-yl-ethyl) ester
Escherichia coli
at 0.03 mM
0.0016
[3-(acetyl(hydroxy)amino)propyl]phosphonic acid mono(2-naphthalen-2-yl-ethyl) ester
Escherichia coli
at 0.03 mM
0.0039
[3-(acetyl(hydroxy)amino)propyl]phosphonic acid mono-n-butyl ester
Escherichia coli
at 0.03 mM
0.016
[3-(acetyl(hydroxy)amino)propyl]phosphonic acid mono-n-propyl ester
Escherichia coli
at 0.03 mM
0.05
[3-(acetyl(hydroxy)amino)propyl]phosphonic acid monomethyl ester
Escherichia coli
at 0.03 mM
0.00049
[3-(acetyl(hydroxy)amino)propyl]phosphonic acid monophenethyl ester
Escherichia coli
at 0.03 mM
0.023
[3-(acetyl(hydroxy)amino)propyl]phosphonic monoethyl ester
Escherichia coli
at 0.03 mM
0.21
[3-[acetyl(hydroxy)amino]-1-(2-bromophenyl)propyl]phosphonic acid
Mycobacterium tuberculosis
pH 7,5, 22°C
0.205
[3-[acetyl(hydroxy)amino]-1-(2-methylphenyl)propyl]phosphonic acid
Mycobacterium tuberculosis
pH 7,5, 22°C
0.00009 - 0.000119
[3-[acetyl(hydroxy)amino]-1-(3,4-dichlorophenyl)propyl]phosphonic acid
0.00031 - 0.00044
[3-[acetyl(hydroxy)amino]-1-(pyridin-3-yl)propyl]phosphonic acid
0.00046 - 0.00063
[3-[acetyl(hydroxy)amino]-1-(pyridin-4-yl)propyl]phosphonic acid
0.0017 - 0.0035
[3-[acetyl(hydroxy)amino]-1-phenylpropyl]phosphonic acid
0.15
[3-[acetyl(hydroxy)amino]-1-[2-(2-hydroxyethyl)phenyl]propyl]phosphonic acid
Mycobacterium tuberculosis
pH 7,5, 22°C
0.465
[3-[acetyl(hydroxy)amino]-1-[2-(hydroxymethyl)phenyl]propyl]phosphonic acid
Mycobacterium tuberculosis
pH 7,5, 22°C
0.00018 - 0.00034
[3-[formyl(hydroxy)amino]-1-(pyridin-3-yl)propyl]phosphonic acid
0.00017 - 0.00018
[3-[formyl(hydroxy)amino]-1-(pyridin-4-yl)propyl]phosphonic acid
0.0178
[3-[hydroxy(3-phenylpropanoyl)amino]propyl]phosphonic acid
Mycobacterium tuberculosis
-
pH not specified in the publication, temperature not specified in the publication
0.064
[4-(2-acetylanilino)-4-oxobutyl]phosphonic acid, [4-(2-fluoroanilino)-4-oxobutyl]phosphonic acid
Plasmodium falciparum
above, pH and temperature not specified in the publication
-
0.00017 - 0.00148
[4-(hydroxyamino)-4-oxobutyl]phosphonic acid
0.93
[4-(methoxyamino)-4-oxobutyl]phosphonic acid
Escherichia coli
pH and temperature not specified in the publication
-
0.064
[4-[2-(methanesulfonyl)anilino]-4-oxobutyl]phosphonic acid
Plasmodium falciparum
above, pH and temperature not specified in the publication
-
0.000048 - 0.00041
[4-[hydroxy(methyl)amino]-4-oxobutyl]phosphonic acid
-
3.8
[4-[methoxy(methyl)amino]-4-oxobutyl]phosphonic acid
Escherichia coli
pH and temperature not specified in the publication
-
0.004
[[(isoquinolin-1-yl)amino]methylene]bis(phosphonic acid)
Escherichia coli
pH and temperature not specified in the publication
-
0.000087
([[acetyl(hydroxy)amino]methoxy]methyl)phosphonic acid
Escherichia coli
pH and temperature not specified in the publication
-
0.00036
([[acetyl(hydroxy)amino]methoxy]methyl)phosphonic acid
Plasmodium falciparum
pH and temperature not specified in the publication
-
0.0011
([[formyl(hydroxy)amino]methoxy]methyl)phosphonic acid
Escherichia coli
pH and temperature not specified in the publication
-
0.0049
([[formyl(hydroxy)amino]methoxy]methyl)phosphonic acid
Plasmodium falciparum
pH and temperature not specified in the publication
-
0.0038
2-[(5Z)-5-(3,4-dihydroxybenzylidene)-4-oxo-2-thioxo-1,3-thiazolidin-3-yl]-N-hydroxyacetamide
Escherichia coli
pH 7.5, 37°C
0.0061
2-[(5Z)-5-(3,4-dihydroxybenzylidene)-4-oxo-2-thioxo-1,3-thiazolidin-3-yl]-N-hydroxyacetamide
Escherichia coli
presence of 0.01% Triton X-100, pH 7.5, 37°C
0.000077
2-[acetyl(hydroxy)amino]ethyl phosphate
Escherichia coli
pH and temperature not specified in the publication
-
0.000279
2-[acetyl(hydroxy)amino]ethyl phosphate
Mycobacterium tuberculosis
pH and temperature not specified in the publication
-
0.000077
2-[acetyl(methyl)amino]ethyl phosphate
Escherichia coli
pH 7.5, 37°C, recombinant His-tagged enzyme
-
0.000279
2-[acetyl(methyl)amino]ethyl phosphate
Mycolicibacterium smegmatis
pH 7.5, 37°C, recombinant His-tagged enzyme
-
0.000342
2-[formyl(hydroxy)amino]ethyl phosphate
Escherichia coli
pH and temperature not specified in the publication
-
0.0021
2-[formyl(hydroxy)amino]ethyl phosphate
Mycobacterium tuberculosis
pH and temperature not specified in the publication
-
0.00312
3,3-dimethyl-11-phenyl-2,3,4,5,10,11-hexahydro-1H-dibenzo[b,e][1,4]diazepin-1-one
Plasmodium falciparum
pH 7.5, 22°C
-
0.125
3,3-dimethyl-11-phenyl-2,3,4,5,10,11-hexahydro-1H-dibenzo[b,e][1,4]diazepin-1-one
Plasmodium falciparum
pH 7.5, 22°C
-
0.0093
3-(hydroxy([(2-phenylbutanoyl)amino]acetyl)amino)propylphosphonic acid
Plasmodium falciparum
-
-
0.02
3-(hydroxy([(2-phenylbutanoyl)amino]acetyl)amino)propylphosphonic acid
Escherichia coli
-
-
0.0096
3-(hydroxy([(3-methylbutanoyl)amino]acetyl)amino)propylphosphonic acid
Plasmodium falciparum
-
-
0.012
3-(hydroxy([(3-methylbutanoyl)amino]acetyl)amino)propylphosphonic acid
Escherichia coli
-
-
0.0004
3-(hydroxy([(4-phenoxybutanoyl)amino]acetyl)amino)propylphosphonic acid
Plasmodium falciparum
-
-
0.001
3-(hydroxy([(4-phenoxybutanoyl)amino]acetyl)amino)propylphosphonic acid
Escherichia coli
-
-
0.019
3-(hydroxy([(4-phenylbutanoyl)amino]acetyl)amino)propylphosphonic acid
Escherichia coli
-
-
0.02
3-(hydroxy([(4-phenylbutanoyl)amino]acetyl)amino)propylphosphonic acid
Plasmodium falciparum
-
-
0.0026
3-(hydroxyamino)-3-oxopropyl phosphate
Escherichia coli
pH 7.5, 37°C, recombinant His-tagged enzyme
-
0.0092
3-(hydroxyamino)-3-oxopropyl phosphate
Mycolicibacterium smegmatis
pH 7.5, 37°C, recombinant His-tagged enzyme
-
0.012
3-[(([(3,4-dimethoxyphenyl)acetyl]amino)acetyl)(hydroxy)amino]propylphosphonic acid
Plasmodium falciparum
-
-
0.014
3-[(([(3,4-dimethoxyphenyl)acetyl]amino)acetyl)(hydroxy)amino]propylphosphonic acid
Escherichia coli
-
-
0.0033
3-[([(cyclopropylcarbonyl)amino]acetyl)(hydroxy)amino]propylphosphonic acid
Plasmodium falciparum
-
-
0.0071
3-[([(cyclopropylcarbonyl)amino]acetyl)(hydroxy)amino]propylphosphonic acid
Escherichia coli
-
-
0.0029
3-[hydroxy(([3-(trifluoromethoxy)benzoyl]amino)acetyl)amino]propylphosphonic acid
Plasmodium falciparum
-
-
0.0051
3-[hydroxy(([3-(trifluoromethoxy)benzoyl]amino)acetyl)amino]propylphosphonic acid
Escherichia coli
-
-
0.0066
3-[hydroxy(([4-(1H-indol-3-yl)butanoyl]amino)acetyl)amino]propylphosphonic acid
Plasmodium falciparum
-
-
0.017
3-[hydroxy(([4-(1H-indol-3-yl)butanoyl]amino)acetyl)amino]propylphosphonic acid
Escherichia coli
-
-
0.000046
3-[hydroxy(methyl)amino]-3-oxopropyl phosphate
Escherichia coli
pH 7.5, 37°C, recombinant His-tagged enzyme
-
0.000233
3-[hydroxy(methyl)amino]-3-oxopropyl phosphate
Mycolicibacterium smegmatis
pH 7.5, 37°C, recombinant His-tagged enzyme
-
0.04
ethyl 2-(2-ethoxy-2-oxoethyl)-2,5-dihydro-1H-benzo[b][1,4]diazepine-3-carboxylate
Plasmodium falciparum
pH 7.5, 22°C
-
0.125
ethyl 2-(2-ethoxy-2-oxoethyl)-2,5-dihydro-1H-benzo[b][1,4]diazepine-3-carboxylate
Plasmodium falciparum
pH 7.5, 22°C
-
0.000342
fosfoxacin
Escherichia coli
pH 7.5, 37°C, recombinant His-tagged enzyme
0.0021
fosfoxacin
Mycolicibacterium smegmatis
pH 7.5, 37°C, recombinant His-tagged enzyme
0.000008
fosmidomycin
Escherichia coli
pH and temperature not specified in the publication
0.000032
fosmidomycin
Plasmodium falciparum
-
-
0.000035
fosmidomycin
Escherichia coli
pH 7.5, 30°C
0.000035
fosmidomycin
Escherichia coli
at 0.03 mM
0.000036
fosmidomycin
Plasmodium falciparum
pH and temperature not specified in the publication
0.000042
fosmidomycin
Escherichia coli
pH 7.5, 37°C, recombinant His-tagged enzyme
0.00005
fosmidomycin
Escherichia coli
-
-
0.000054
fosmidomycin
Mycobacterium tuberculosis
-
pH 7.5, 25°C, recombinant enzyme
0.00008
fosmidomycin
Mycobacterium tuberculosis
pH 7.5, 22°C
0.00008
fosmidomycin
Mycobacterium tuberculosis
-
pH 7.5, 22°C
0.00008
fosmidomycin
Mycobacterium tuberculosis
pH and temperature not specified in the publication
0.000247
fosmidomycin
Francisella tularensis
-
pH 7.8, 22°C
0.000301
fosmidomycin
Plasmodium falciparum
-
0.00031
fosmidomycin
Mycobacterium tuberculosis
-
IC50: 310 nM for the forward reaction, 0.0027 mM for the reverse reaction, Gram positive bacteria, including Mycobacterium tuberculosis, are resistant against the antibiotic fosmidomycin, which is an inhibitor of the enzyme from most gram-negative bacteri
0.00044
fosmidomycin
Plasmodium falciparum
pH 7.5, 22°C, IC50 versus proliferation of Plasmodium falciparum strain Dd2
0.00045
fosmidomycin
Plectranthus barbatus
IC50: 450 nM, recombinant enzyme, inhibition of growth and forskolin production in vivo
0.00051
fosmidomycin
Mycolicibacterium smegmatis
pH 7.5, 37°C, recombinant His-tagged enzyme
0.00071
fosmidomycin
Yersinia pestis
pH 7.8, 37°C
0.00117
fosmidomycin
Plasmodium falciparum
pH 7.5, 22°C, IC50 versus proliferation of Plasmodium falciparum strain 3D7
0.0027
fosmidomycin
Mycobacterium tuberculosis
-
IC50: 310 nM for the forward reaction, 0.0027 mM for the reverse reaction, Gram positive bacteria, including Mycobacterium tuberculosis, are resistant against the antibiotic fosmidomycin, which is an inhibitor of the enzyme from most gram-negative bacteri
93
fosmidomycin
Thermotoga maritima
pH 7.5, 50°C
107
fosmidomycin
Thermotoga maritima
pH 7.5, 85°C
0.000018
FR-900098
Plasmodium falciparum
-
-
0.000018
FR-900098
Plasmodium falciparum
pH and temperature not specified in the publication
0.00003
FR-900098
Escherichia coli
pH and temperature not specified in the publication
0.000051
FR-900098
Escherichia coli
-
-
0.00016
FR-900098
Mycobacterium tuberculosis
pH and temperature not specified in the publication
0.00032
FR-900098
Mycolicibacterium smegmatis
pH 7.5, 37°C, recombinant His-tagged enzyme
0.000004
FR900098
Escherichia coli
pH 7.5, 37°C, recombinant His-tagged enzyme
0.000035
FR900098
Escherichia coli
pH 7.5, 30°C
0.000035
FR900098
Escherichia coli
at 0.03 mM
0.00016
FR900098
Mycobacterium tuberculosis
pH 7.5, 22°C
0.00023
FR900098
Yersinia pestis
pH 7.8, 37°C
0.118
FR900098
Plasmodium falciparum
-
0.0000045
[(3,4-dichlorophenyl)([2-[hydroxy(methyl)amino]-2-oxoethyl]sulfanyl)methyl]phosphonic acid
Plasmodium falciparum
pH and temperature not specified in the publication
-
0.0000059
[(3,4-dichlorophenyl)([2-[hydroxy(methyl)amino]-2-oxoethyl]sulfanyl)methyl]phosphonic acid
Escherichia coli
pH and temperature not specified in the publication
-
0.0000092
[(3,4-dichlorophenyl)([2-[hydroxy(methyl)amino]-2-oxoethyl]sulfanyl)methyl]phosphonic acid
Mycobacterium tuberculosis
pH and temperature not specified in the publication
-
0.0031
[(5Z)-5-(3,4-dihydroxybenzylidene)-4-oxo-2-thioxo-1,3-thiazolidin-3-yl]acetic acid
Escherichia coli
pH 7.5, 37°C
0.0044
[(5Z)-5-(3,4-dihydroxybenzylidene)-4-oxo-2-thioxo-1,3-thiazolidin-3-yl]acetic acid
Escherichia coli
presence of 0.01% Triton X-100, pH 7.5, 37°C
0.000028
[1-(3,4-dichlorophenyl)-3-[formyl(hydroxy)amino]propyl]phosphonic acid
Plasmodium falciparum
pH and temperature not specified in the publication
0.000059
[1-(3,4-dichlorophenyl)-3-[formyl(hydroxy)amino]propyl]phosphonic acid
Escherichia coli
pH and temperature not specified in the publication
0.00009
[3-[acetyl(hydroxy)amino]-1-(3,4-dichlorophenyl)propyl]phosphonic acid
Plasmodium falciparum
pH and temperature not specified in the publication
0.000119
[3-[acetyl(hydroxy)amino]-1-(3,4-dichlorophenyl)propyl]phosphonic acid
Escherichia coli
pH and temperature not specified in the publication
0.00031
[3-[acetyl(hydroxy)amino]-1-(pyridin-3-yl)propyl]phosphonic acid
Plasmodium falciparum
pH 7.5, 22°C, IC50 versus proliferation of Plasmodium falciparum strain Dd2
0.00044
[3-[acetyl(hydroxy)amino]-1-(pyridin-3-yl)propyl]phosphonic acid
Plasmodium falciparum
pH 7.5, 22°C, IC50 versus proliferation of Plasmodium falciparum strain 3D7
0.00046
[3-[acetyl(hydroxy)amino]-1-(pyridin-4-yl)propyl]phosphonic acid
Plasmodium falciparum
pH 7.5, 22°C, IC50 versus proliferation of Plasmodium falciparum strain Dd2
0.00063
[3-[acetyl(hydroxy)amino]-1-(pyridin-4-yl)propyl]phosphonic acid
Plasmodium falciparum
pH 7.5, 22°C, IC50 versus proliferation of Plasmodium falciparum strain 3D7
0.0017
[3-[acetyl(hydroxy)amino]-1-phenylpropyl]phosphonic acid
Plasmodium falciparum
pH 7.5, 22°C, IC50 versus proliferation of Plasmodium falciparum strain Dd2
0.0035
[3-[acetyl(hydroxy)amino]-1-phenylpropyl]phosphonic acid
Plasmodium falciparum
pH 7.5, 22°C, IC50 versus proliferation of Plasmodium falciparum strain 3D7
0.00018
[3-[formyl(hydroxy)amino]-1-(pyridin-3-yl)propyl]phosphonic acid
Plasmodium falciparum
pH 7.5, 22°C, IC50 versus proliferation of Plasmodium falciparum strain Dd2
0.00034
[3-[formyl(hydroxy)amino]-1-(pyridin-3-yl)propyl]phosphonic acid
Plasmodium falciparum
pH 7.5, 22°C, IC50 versus proliferation of Plasmodium falciparum strain 3D7
0.00017
[3-[formyl(hydroxy)amino]-1-(pyridin-4-yl)propyl]phosphonic acid
Plasmodium falciparum
pH 7.5, 22°C, IC50 versus proliferation of Plasmodium falciparum strain Dd2
0.00018
[3-[formyl(hydroxy)amino]-1-(pyridin-4-yl)propyl]phosphonic acid
Plasmodium falciparum
pH 7.5, 22°C, IC50 versus proliferation of Plasmodium falciparum strain 3D7
0.00017
[4-(hydroxyamino)-4-oxobutyl]phosphonic acid
Escherichia coli
pH 7.5, 37°C, recombinant His-tagged enzyme
0.00017
[4-(hydroxyamino)-4-oxobutyl]phosphonic acid
Escherichia coli
pH and temperature not specified in the publication
0.00148
[4-(hydroxyamino)-4-oxobutyl]phosphonic acid
Mycolicibacterium smegmatis
pH 7.5, 37°C, recombinant His-tagged enzyme
0.000048
[4-[hydroxy(methyl)amino]-4-oxobutyl]phosphonic acid
Escherichia coli
pH 7.5, 37°C, recombinant His-tagged enzyme
-
0.000048
[4-[hydroxy(methyl)amino]-4-oxobutyl]phosphonic acid
Escherichia coli
pH and temperature not specified in the publication
-
0.00041
[4-[hydroxy(methyl)amino]-4-oxobutyl]phosphonic acid
Mycolicibacterium smegmatis
pH 7.5, 37°C, recombinant His-tagged enzyme
-
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evolution
Dioscorea zingiberensis DzDXR is highly homologous to other plant DXRs, especially to those in monocotyledons
evolution
phylogenetic analysis, rice DXR is encoded by the single copy gene OsDXR and phylogenetically categorized into plant DXR clade II, which includes the tree plants gingko, yew, and pine, and the Poaceae family plants sorghum (Sorghum bicolor), maize, foxtail millet, and barley (Hordeum vulgare). On the other hand, rice DXR is not categorized into clade I, which includes herbage plants
malfunction
DXR is essential for the survival of the pathogen, and its inhibition leads to the antimalarial action
malfunction
DXR is essential for the survival of the pathogen, and its inhibition leads to the antitubercular action
malfunction
MH018577
increased expression of SaDXR leads to increased contents of sandalwood sesquiterpenoids, such as alpha-santalol and beta-santalol, in the stems of young sandalwood trees
malfunction
overexpression of PtDXR in transgenic poplars improves tolerance to abiotic and biotic stresses. Increased transcript levels of PtDXR alter the response to Septotinia populiperda. The spread and extent of pathogens in the wild-type plants are faster and greater than in the transgenic lines, based on analysis of the length and width of the largest pathogenic region
malfunction
the overexpression of each OsDXS2 or OsDXR causes no positive effect on the accumulation of either carotenoids or chlorophylls in leaves and seeds, but overexpression of either OsDXS2 or OsDXR affects seed carotenoid metabolism, total carotenoid content is increased by 26% in the PGD1::OsDXS2 lines and decreased by 11% in the PGD1::OsDXR lines, overview. The endogenous expression of OsDXS1 and OsDXS2 increases up to 6.7fold and 4.0fold, respectively, following the overexpression of OsDXR, but the enhanced activity of OsDXS2 does not cause a significant increase in OsDXR expression, even though the expression of the OsPSY2 gene is significantly increased up to 5.7fold following the overexpression of OsDXS2
malfunction
-
DXR is essential for the survival of the pathogen, and its inhibition leads to the antitubercular action
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malfunction
-
DXR is essential for the survival of the pathogen, and its inhibition leads to the antitubercular action
-
metabolism
-
1-deoxy-D-xylulose-5-phosphate, DXP, reductoisomerase catalyzes the first committed step in the 2-C-methyl-D-erythritol 4-phosphate pathway involving a skeletal rearrangement of DXP via a retroaldol/aldol process followed by reduction by NADPH to yield 2-C-methyl-D-erythritol 4-phosphate
metabolism
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the 1-deoxy-D-xylulose-5-phosphate reductoisomerase is the second enzyme in the nonmevalonate isoprene biosynthesis pathway, catalyzing the reductive isomerization of 1-deoxy-D-xylulose-5-phosphate to 2-methyl-D-erythritol-4-phosphate for making isopentenyl diphosphate and dimethylallyl diphosphate
metabolism
the 1-deoxy-D-xylulose-5-phosphate reductoisomerase is the second enzyme in the nonmevalonate isoprene biosynthesis pathway, catalyzing the reductive isomerization of 1-deoxy-D-xylulose-5-phosphate to 2-methyl-D-erythritol-4-phosphate for making isopentenyl diphosphate and dimethylallyl diphosphate
metabolism
the enzyme catalyzes the second regulation step in the 2-C-methyl-D-erythritol 4-phosphate pathway and the the first committed step of the 2-C-methyl-D-erythritol 4-phosphate pathway for isoprenoid biosynthesis
metabolism
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the enzyme is involved in a parasite-specific, isoprenoid biosynthetic DOXP/MEP pathway
metabolism
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the enzyme is involved in the isoprenoid biosynthetic DOXP/MEP pathway
metabolism
1-deoxy-D-xylulose 5-phosphate reductoisomerase (DXR) is the first key enzyme in the MEP pathway for terpenoid biosynthesis
metabolism
1-deoxy-D-xylulose 5-phosphate-reductoisomerase (DXR,) is the key enzyme in the plastidic 2-C-methyl-D-erythritol 4-phosphate (MEP) pathway. In contrast to the DzDXR transcription, diosgenin is present predominantly in tubers and in minute quantities in leaves. Because diosgenin is very likely formed mainly in the cytosol of mature leaf cells of Dioscorea zingiberensis and the plastidic IPP and DMAPP produced by the MEP pathway can be transported into the cytosol, the consistently high expression of DzDXR detected in mature leaf of Dioscorea zingiberensis implies that the MEP pathway might play a significant role in diosgenin biosynthesis
metabolism
1-deoxy-D-xylulose-5-phosphate reductoisomerase (DXR) catalyzes the second step of the nonmevalonate (or MEP) pathway that functions in several organisms and plants for the synthesis of isoprenoids
metabolism
1-deoxy-D-xylulose-5-phosphate reductoisomerase (DXR) catalyzes the second step of the nonmevalonate (or MEP) pathway that functions in several organisms and plants for the synthesis of isoprenoids
metabolism
1-deoxy-D-xylulose-5-phosphate reductoisomerase (DXR) catalyzes the second step of the nonmevalonate (or MEP) pathway that functions in several organisms and plants for the synthesis of isoprenoids
metabolism
MH018577
1-deoxy-D-xylulose-5-phosphate reductoisomerase (DXR) is a rate-limiting enzyme that transforms 1-deoxy-D-xylulose 5-phosphate (DXP) to 2-C-methyl-D-erythritol 4-phosphate (MEP) and controls flux through the MEP pathway. Relationship between SaDXR and the biosynthesis of chlorophylls, carotenoids, and sandalwood-specific sesquiterpenoids, overview
metabolism
1-deoxy-D-xylulose-5-phosphate reductoisomerase (DXR), an important enzyme in the 2-C-methyl-D-erythritol-4-phosphate (MEP) pathway in plant plastids, provides the basic five-carbon units for isoprenoid biosynthesis. Roles of the MEP pathway in regulating growth, development, and artemisinin biosynthesis of Artemisia annua
metabolism
1-deoxy-D-xylulose-5-phosphate synthase (DXS) and 1-deoxy-D-xylulose-5-phosphate reductoisomerase (DXR) are key enzymes in terpenoid biosynthesis. The first two rate-limiting enzymes in the plastid-located 2-C-methyl-D-erythritol-4-phosphate (MEP) pathway are 1-deoxy-D-xylulose-5-phosphate synthase (DXS) and 1-deoxy-D-xylulose-5-phosphate reductoisomerase (DXR). The first major step involves DXS-dependent catalysis of pyruvate and D-glyceraldehyde-3-phosphate to form 1-deoxy-D-xylulose-5-phosphate (DXP). The second step is catalyzed by DXR and generates MEP, followed by several enzymatic reactions to produce precursors of IPP and DMAPP. DXS catalyzes the formation of 1-deoxy-D-xylulose 5-phosphate (DXP) from pyruvate and D-glyceraldehyde-3-phosphate. DXR catalyzes the formation of 2-C-methyl-D-erythritol 4-phosphate (MEP) from DXP
metabolism
induction of DXR expression causes increased thymol and carvacrol production
metabolism
organ-specific differential roles of rice Deoxyxylulose 5-phosphate synthase (DXS) and deoxyxylulose 5-phosphate reductoisomerase (DXR), the first two enzymes of the methylerythritol 4-phosphate (MEP) pathway, in carotenoid metabolism in Oryza sativa leaves and seeds. DXS and DXR are the enzymes that catalyze the first two enzyme steps of the MEP pathway to supply the isoprene building-blocks of carotenoids. Enzyme OsDXS2 functions as a rate-limiting enzyme supplying IPP/DMAPPs to seed carotenoid metabolism, but OsDXR does not in either leaves or seeds. Carotenoid and MEP pathway regulation, overview
metabolism
rate-limiting enzyme in the 2-methyl-D-erythritol-4-phosphate (MEP) terpenoid biosynthetic pathway catalyzing the second step
metabolism
the 1-deoxy-D-xylulose-5-phosphate reductoisomerase (DXR) is the rate-limiting enzyme in the methylerythritol 4-phosphate pathway (MEP) via conversion of 1-deoxy-D-xylulose-5-phosphate (DXP) into MEP
metabolism
the enzyme catalyzes the first comitted step in the methyl erythritol phosphate (MEP) pathway
metabolism
the enzyme catalyzes the first comitted step in the methyl erythritol phosphate (MEP) pathway
metabolism
the enzyme catalyzes the first comitted step in the methyl erythritol phosphate (MEP) pathway
metabolism
the enzyme is involved in the 2-methyl-D-erythritol-4-phosphate (MEP) terpenoid biosynthetic pathway catalyzing the second step, pathway overview
metabolism
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the enzyme is involved in the 2C-methyl-D-erythritol 4-phosphate (MEP) pathway in leaves. The MEP pathway initiates the biosynthesis of highly valuable monoterpene indole alkaloids (MIAs). The MIA biosynthetic pathway shows in leaves a complex compartmentation occuring at both the cellular and subcellular levels, notably for some gene products of the MEP pathway. All MEP pathway genes are coordinately and mainly expressed in internal phloem-associated parenchyma of young leaves, reinforcing the role of this tissue in MIA biosynthesis. A potential role of stromules in enhancing MIA precursor exchange with other cell compartments to favor metabolic fluxes towards the MIA biosynthesis. The MEP pathway produces both isopentenyl diphosphate (IPP) and dimethylallyl diphosphate (DMAPP) through seven enzymatic reactions initiated by the synthesis of 1-deoxy-D-xylulose 5-phosphate (DXP) from pyruvate and glyceraldehyde 3-phosphate. This reaction is catalyzed by DXP synthase (DXS), encoded by a small gene family in higher plants. The DXS isogenes have been clustered into two related gene groups: Clade I-DXS including housekeeping genes and Clade II-DXS including genes associated with plant defense and secondary metabolism. DXP is then sequentially converted into MEP by DXP reductoisomerase (DXR) and into 4-(cytidine 5'-diphospho)-2-C-methyl-D-erythritol (CDP-ME) following the addition of cytidine triphosphate by CDP-ME synthase (CMS), pathway overview. MEP pathway enzymes are targeted to plastids
metabolism
-
the enzyme catalyzes the first comitted step in the methyl erythritol phosphate (MEP) pathway
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metabolism
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the enzyme catalyzes the first comitted step in the methyl erythritol phosphate (MEP) pathway
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metabolism
-
the enzyme is involved in the 2-methyl-D-erythritol-4-phosphate (MEP) terpenoid biosynthetic pathway catalyzing the second step, pathway overview
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metabolism
-
the enzyme catalyzes the first comitted step in the methyl erythritol phosphate (MEP) pathway
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metabolism
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1-deoxy-D-xylulose-5-phosphate reductoisomerase (DXR) catalyzes the second step of the nonmevalonate (or MEP) pathway that functions in several organisms and plants for the synthesis of isoprenoids
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metabolism
-
the enzyme catalyzes the first comitted step in the methyl erythritol phosphate (MEP) pathway
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metabolism
-
1-deoxy-D-xylulose-5-phosphate reductoisomerase (DXR) catalyzes the second step of the nonmevalonate (or MEP) pathway that functions in several organisms and plants for the synthesis of isoprenoids
-
physiological function
-
influence on plaunotol biosynthesis
physiological function
Vitis vinifera x Vitis vinifera
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involved in terpenoid metabolism
physiological function
-
involved in terpenoid metabolism
physiological function
involved in the 2-C-methyl-D-erythritol 4-phosphate pathway
physiological function
-
a dxr gene T-DNA insertion mutant shows albino and dwarf phenotype. The mutant does not bolt, has a significantly reduced number of trichomes and most of the stomata cannot close normally in the leaves. Two transgenic co-suppression lines produce more yellow inflorescences and albino sepals with no trichomes. The transcription levels of genes involved in trichome initiation are strongly affected in the mutants. Exogenous application of gibberellic acid GA3 can partially rescue the dwarf phenotype and the trichome initiation of the insertion mutant, and exogenous application of abscisic acid can rescue the stomata closure defect
physiological function
-
1-deoxy-D-xylulose-5-phosphate reductoisomerase in the non-mevalonate isoprene biosynthesis pathway is essential to the organism
physiological function
-
in transgenic spike lavender plants (Lavandula latifolia) constitutively expressing the Arabidopsis thaliana DXR gene, a clear correlation between transcript accumulation and monoterpene production cannot be established. The DXR enzyme does not play a crucial role in the synthesis of plastidial monoterpene precursors
physiological function
-
1-deoxy-xylulose-5-phosphate isomerase-reductase gene (DXR), catalyzes the NADP-dependent rearrangement and reduction of 1-deoxy-D-xylulose-5-phosphate (DXP) to 2-C-methyl-D-erythritol 4-phosphate (MEP), which is the key element for MEP-pathway that supports the main C5 units for the formation of mono and diterpenes. Plastidial MEP pathway is considered as the main important source of precursors for essential plastid isoprenoids
physiological function
DXR is essential for the survival of multiple pathogenic bacteria/parasites
physiological function
DXR is essential for the survival of multiple pathogenic bacteria/parasites, including those that cause tuberculosis and malaria in humans
physiological function
DXR is essential for the survival of multiple pathogenic bacteria/parasites, including those that cause tuberculosis and malaria in humans
physiological function
enzyme OsDXS2 functions as a rate-limiting enzyme supplying IPP/DMAPPs to seed carotenoid metabolism, but OsDXR does not in either leaves or seeds. DXR plays essential roles in the development and survival of plants. No positive effect of OsDXR on carotenoid and chlorophyll metabolism in rice leaves. OsDXR-mediated transcriptional alteration of intrinsic carotenogenetic genes in rice leaves and seeds, overview
physiological function
MH018577
enzyme SaDXR protein may be involved in plastidial isoprenoid biosynthesis in plants
physiological function
in many pathogenic bacteria, the enzymes of the 2-C-methyl-D-erythrirol 4-phosphate (MEP) pathway are involved in the biosynthesis of isopentenyl diphosphate and dimethylallyl diphosphate, the two universal and essential units for the biosynthesis of isoprenoids. The enzyme 1-deoxyxylulose 5-phosphate reductoisomerase (DXR) that catalyzes the transformation of 1-deoxy-D-xylulose 5-phosphate (DXP) to 2-C-methyl-D-erythritol 4-phosphate (MEP) via an isomerization and a NADPH-dependent reduction reaction
physiological function
in many pathogenic bacteria, the enzymes of the 2-C-methyl-D-erythrirol 4-phosphate (MEP) pathway are involved in the biosynthesis of isopentenyl diphosphate and dimethylallyl diphosphate, the two universal and essential units for the biosynthesis of isoprenoids. The enzyme 1-deoxyxylulose 5-phosphate reductoisomerase (DXR) that catalyzes the transformation of 1-deoxy-D-xylulose 5-phosphate (DXP) to 2-C-methyl-D-erythritol 4-phosphate (MEP) via an isomerization and a NADPH-dependent reduction reaction
physiological function
PtDXR encodes a functional protein, and widely participates in plant growth and development, stress physiological process
physiological function
the 1-deoxy-D-xylulose-5-phosphate reductoisomerase (DXR), an NADPH-dependent reductase, plays a pivotal role in the methylerythritol 4-phosphate pathway (MEP), in the conversion of 1-deoxy-D-xylulose-5-phosphate (DXP) into MEP. Structure-function analysis of DXR and regulatory mechanism, molecular dynamics simulations, overview
physiological function
-
in many pathogenic bacteria, the enzymes of the 2-C-methyl-D-erythrirol 4-phosphate (MEP) pathway are involved in the biosynthesis of isopentenyl diphosphate and dimethylallyl diphosphate, the two universal and essential units for the biosynthesis of isoprenoids. The enzyme 1-deoxyxylulose 5-phosphate reductoisomerase (DXR) that catalyzes the transformation of 1-deoxy-D-xylulose 5-phosphate (DXP) to 2-C-methyl-D-erythritol 4-phosphate (MEP) via an isomerization and a NADPH-dependent reduction reaction
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physiological function
-
DXR is essential for the survival of multiple pathogenic bacteria/parasites, including those that cause tuberculosis and malaria in humans
-
physiological function
-
DXR is essential for the survival of multiple pathogenic bacteria/parasites, including those that cause tuberculosis and malaria in humans
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additional information
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role of the nonreacting phosphorylmethyl group in catalysis, overview
additional information
two substrate-binding domains, LPADSEHSAI and NKGLEVIEAHY, locate in its mid-region of the enzyme molecule, which is highly homologous to DXRs from other plants and similar to the DXR from Escherichia coli
additional information
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two substrate-binding domains, LPADSEHSAI and NKGLEVIEAHY, locate in its mid-region of the enzyme molecule, which is highly homologous to DXRs from other plants and similar to the DXR from Escherichia coli
additional information
enzyme active site structure analysis
additional information
-
enzyme active site structure analysis
additional information
enzyme CaDXR contains three conserved domain, namely NADPH (GSTGSIGT and LAAGSNV), substrate binding (LPADSEHSAI and NKGLEVIEAHY) and Cys-Ser-(Ala/Met/Val/Thr) cleavage-site domains. Three-dimensional molecular modeling and model validation, and molecular dynamics simulation of modeled DXR, overview
additional information
-
enzyme CaDXR contains three conserved domain, namely NADPH (GSTGSIGT and LAAGSNV), substrate binding (LPADSEHSAI and NKGLEVIEAHY) and Cys-Ser-(Ala/Met/Val/Thr) cleavage-site domains. Three-dimensional molecular modeling and model validation, and molecular dynamics simulation of modeled DXR, overview
additional information
-
enzyme active site structure analysis
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E231K
less than 0.24% wild type kcat
D151N/E222Q
loss of catalytic ability, loss of binding of Mn2+. Crystallization data
W203A
complete loss of activity
W203F
turnover is largely limited by product release for the wild-type enzyme, chemistry is significantly more rate-limiting for mutants W203F and W203Y. Mutant is more sensitive to fosmidomycin than wild-type. Mutation strongly tips the entropy-enthalpy balance of total binding energy
W203G
complete loss of activity
W203Y
turnover is largely limited by product release for the wild-type enzyme, chemistry is significantly more rate-limiting for mutants W203F and W203Y. Mutant is more sensitive to fosmidomycin than wild-type. Mutation strongly tips the entropy-enthalpy balance of total binding energy
D151N/E222Q
-
loss of catalytic ability, loss of binding of Mn2+. Crystallization data
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W203A
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complete loss of activity
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W203F
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turnover is largely limited by product release for the wild-type enzyme, chemistry is significantly more rate-limiting for mutants W203F and W203Y. Mutant is more sensitive to fosmidomycin than wild-type. Mutation strongly tips the entropy-enthalpy balance of total binding energy
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W203G
-
complete loss of activity
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W203Y
-
turnover is largely limited by product release for the wild-type enzyme, chemistry is significantly more rate-limiting for mutants W203F and W203Y. Mutant is more sensitive to fosmidomycin than wild-type. Mutation strongly tips the entropy-enthalpy balance of total binding energy
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H219Q
site-directed mutagenesis, the mutation decreased the affinity toward the substrate 1-deoxy-D-xylulose 5-phosphate with an 8-fold increase in the Km compared to the wild-type enzyme
D152A
-
site-directed mutagenesis, active site mutant, in sense and antisense orientation, 4.1% activity compared to the wild-type enzyme
D152N
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site-directed mutagenesis, active site mutant, in sense and antisense orientation, inactive mutant
E154D
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site-directed mutagenesis, active site mutant, in sense and antisense orientation, 0.28% activity compared to the wild-type enzyme
E154Q
-
site-directed mutagenesis, active site mutant, in sense and antisense orientation, 0.008% activity compared to the wild-type enzyme
E223H
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site-directed mutagenesis, active site mutant, in sense and antisense orientation, 0.007% activity compared to the wild-type enzyme
E223Q
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site-directed mutagenesis, active site mutant, in sense and antisense orientation, inactive mutant
H155A
-
site-directed mutagenesis, active site mutant, in sense and antisense orientation, 32% activity compared to the wild-type enzyme
M206A
-
site-directed mutagenesis, active site mutant, in sense and antisense orientation, 9% activity compared to the wild-type enzyme
M206V
-
site-directed mutagenesis, active site mutant, in sense and antisense orientation, inactive mutant
S153A
-
site-directed mutagenesis, active site mutant, in sense and antisense orientation, 0.11% activity compared to the wild-type enzyme
S153N
-
site-directed mutagenesis, active site mutant, in sense and antisense orientation, 0.76% activity compared to the wild-type enzyme
S153T
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site-directed mutagenesis, active site mutant, in sense and antisense orientation, 4.8% activity compared to the wild-type enzyme
W204A
-
site-directed mutagenesis, the mutant shows reduced activity and altered kinetics compared to the wild-type enzyme
W204F
-
site-directed mutagenesis, the mutant shows reduced activity and altered kinetics compared to the wild-type enzyme, the mutant is active with the substrate analogue 1,2-dideoxy-D-threo-3-hexulose 6-phosphate in contrast to the wild-type enzyme
W204L
-
site-directed mutagenesis, the mutant shows reduced activity and altered kinetics compared to the wild-type enzyme
W204V
-
site-directed mutagenesis, the mutant shows reduced activity and altered kinetics compared to the wild-type enzyme
additional information
2-C-methyl-D-erythritol 4-phosphate pathway gene-disrupted Escherichia coli mutants. DXR is functionally active in Escherichia coli mutant DYM1
additional information
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2-C-methyl-D-erythritol 4-phosphate pathway gene-disrupted Escherichia coli mutants. DXR is functionally active in Escherichia coli mutant DYM1
additional information
DXR gene silencing by RNAi using Agrobacterium tumefaciens strain LBA4404, mutants phenotype, detailed analysis, overview. AaDXR-RNAi plants show no significant variation of stomatal length and density at the abaxial side of leaves. No significant alteration of floral initiation and flower opening is observed in the transgenic plants. The trichome density and area in leaves and flower buds are analyzed by fluorescence microscopy. It is evident that leaves of transgenic Artemisia annua in vegetative stage carry considerably lower density of trichomes than that of control. The trichome area of transgenic Artemisia annua is larger than that of control. During the flower formation, there is no difference of trichome density and area on flower bud surface between transgenic plants and control. Significant decline in chlorphylls Chla and Chlb is found in various growth stages of transgenic plants. Net photosynthesis rate of in DXRRNAi plants is decreased by 20.0-31.4% compared with that of the controls
additional information
functional complementation of Escherichia coli mutant lacking 1-deoxy-D-xylulose 5-phosphate reductoisomerase activity
additional information
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functional complementation of Escherichia coli mutant lacking 1-deoxy-D-xylulose 5-phosphate reductoisomerase activity
additional information
2-C-methyl-D-erythritol 4-phosphate pathway gene-disrupted Escherichia coli mutants. DXR is functionally active in Escherichia coli mutant DYM1
additional information
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2-C-methyl-D-erythritol 4-phosphate pathway gene-disrupted Escherichia coli mutants. DXR is functionally active in Escherichia coli mutant DYM1
additional information
rescuing of Escherichia coli enzyme-knockout mutants by the Ginkgo gene clone from embryonic roots
additional information
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rescuing of Escherichia coli enzyme-knockout mutants by the Ginkgo gene clone from embryonic roots
additional information
2-C-methyl-D-erythritol 4-phosphate pathway gene-disrupted Escherichia coli mutants. DXR is functionally active in Escherichia coli mutant DYM1
additional information
-
2-C-methyl-D-erythritol 4-phosphate pathway gene-disrupted Escherichia coli mutants. DXR is functionally active in Escherichia coli mutant DYM1
additional information
-
removal of C-terminal 18 amino acid residues has no effect on enzyme activity, affinity for substrates or sensitivity to isotopic probes
additional information
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construction of an N-terminal His6-tagged enzyme variant comprising the first 389 of 413 residues, the mutant is more stable and kinetically similar to the wild-type enzyme
additional information
expression profiles of carotenoid biosynthetic genes in leaves and seeds among three independent transgenic plants for each OsDXS2 and OsDXR construct relative to non-transgenic (NT) and stPAC plants. The endogenous expression of OsDXS1 and OsDXS2 increases up to 6.7fold and 4.0fold, respectively, following the overexpression of OsDXR, but the enhanced activity of OsDXS2 does not cause a significant increase in OsDXR expression, even though the expression of the OsPSY2 gene is significantly increased up to 5.7fold following the overexpression of OsDXS2
additional information
recombinant overexpression of PtDXR in transgenic poplars improves tolerance to abiotic and biotic stresses. Overexpression of PtDXR increases plant tolerance to salt stress, the phenotype, RWC, SOD and POD activities. Increased transcript levels of PtDXR increase in response to Septotinia populiperda, the spread and extent of pathogens in the wild-type plants are faster and greater than in the transgenic lines, based on analysis of the length and width of the largest pathogenic region, phenotype overview
additional information
-
recombinant overexpression of PtDXR in transgenic poplars improves tolerance to abiotic and biotic stresses. Overexpression of PtDXR increases plant tolerance to salt stress, the phenotype, RWC, SOD and POD activities. Increased transcript levels of PtDXR increase in response to Septotinia populiperda, the spread and extent of pathogens in the wild-type plants are faster and greater than in the transgenic lines, based on analysis of the length and width of the largest pathogenic region, phenotype overview
additional information
gene complements Escherichia coli mutant deficient of 1-deoxy-D-xylulose 5-phosphate reductoisomerase
additional information
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gene complements Escherichia coli mutant deficient of 1-deoxy-D-xylulose 5-phosphate reductoisomerase
additional information
MH018577
chlorophylls and carotenoids increased in 35S::SaDXR overexpression Arabidopsis thaliana lines
additional information
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chlorophylls and carotenoids increased in 35S::SaDXR overexpression Arabidopsis thaliana lines
additional information
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transplastomic tobacco plants that overproduce enzyme show an increase in the content of various isoprenoids such as chlorophyll, alpha,beta carotene, lutein, antheraxanthin, solanesol and beta-sitosterol with qualitative change in isoprenoid composition. Growth phenotype of transplastomic strains is similar to wild-type
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