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2.5.1.54: 3-deoxy-7-phosphoheptulonate synthase

This is an abbreviated version!
For detailed information about 3-deoxy-7-phosphoheptulonate synthase, go to the full flat file.

Word Map on EC 2.5.1.54

Reaction

phosphoenolpyruvate
+
D-erythrose 4-phosphate
+
H2O
=
3-deoxy-D-arabino-hept-2-ulosonate 7-phosphate
+
phosphate

Synonyms

2-dehydro-3-deoxy-D-arabino-heptonate-7-phosphate D-erythrose-4-phosphate-lyase (pyruvate-phosphorylating), 2-dehydro-3-deoxy-phosphoheptanoate aldolase, 2-dehydro-3-deoxy-phosphoheptonate aldolase, 2-keto-3-deoxy-D-arabino-heptonic acid 7-phosphate synthetase, 3-deoxy-7-phosphoheptulonate synthase, 3-deoxy-D-arabino heptulosonate 7-phosphate synthase, 3-deoxy-D-arabino-2-heptulosonic acid 7-phosphate synthetase, 3-deoxy-D-arabino-heptolosonate-7-phosphate synthetase, 3-deoxy-D-arabino-heptulosonate 7-phosphate synthase, 3-deoxy-D-arabino-heptulosonate 7-phosphate synthetase, 3-deoxy-D-arabino-heptulosonate-7-phosphate synthase, 3-deoxy-D-arabino-heptulosonic acid 7-phosphate synthase, 3-deoxy-D-arabinoheptulosonate 7-phosphate synthase, 3-deoxy-D-arabinoheptulosonate-7-phosphate synthetase, 7-phospho-2-dehydro-3-deoxy-D-arabino-heptonate D-erythrose-4-phosphate-lyase (pyruvate-phosphorylating), 7-phospho-2-keto-3-deoxy-D-arabino-heptonate D-erythrose-4-phosphate lyase (pyruvate-phosphorylating), aldolase, phospho-2-keto-3-deoxyheptanoate, Aro1A, Aro4, Aro4p, AroA, AroA(Q), aroF, AroFFR, AroG, D-erythrose-4-phosphate-lyase, D-erythrose-4-phosphate-lyase (pyruvate-phosphorylating), DAH7-P synthase, DAH7-P synthase (phe), DAH7P, DAH7P synthase, DAH7PS, DAHP synthase, DAHP synthase-phe, DAHP synthase-trp, DAHP synthase-tyr, DAHP(Phe), DAHPS, DAHPS(Tyr), Dax1, deoxy-D-arabino-heptulosonate-7-phosphate synthetase, DHS, DHS1, DS-Co, DS-Mn, EC 4.1.2.15, KDPH synthase, KDPH synthetase, More, mtDAH7Ps, MtDS, NCgl0950 DAHP synthase, NCgl2098 DAHP synthase, Nme-DAH7PS, OsDAHPS, PF1690, phospho-2-dehydro-3-deoxyheptonate aldolase, phospho-2-keto-3-deoxyheptanoate aldolase, Phospho-2-keto-3-deoxyheptonate aldolase, phospho-2-keto-3-deoxyheptonic aldolase, phospho-2-oxo-3-deoxyheptonate aldolase, phzC, TmaDAH7PS

ECTree

     2 Transferases
         2.5 Transferring alkyl or aryl groups, other than methyl groups
             2.5.1 Transferring alkyl or aryl groups, other than methyl groups (only sub-subclass identified to date)
                2.5.1.54 3-deoxy-7-phosphoheptulonate synthase

Inhibitors

Inhibitors on EC 2.5.1.54 - 3-deoxy-7-phosphoheptulonate synthase

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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(1R,2S)-1,2-epoxypropylphosphonic acid
-
-
(2R)-2-(phosphonooxy)propanoic acid
-
mimicking phosphohemiketal 2 (instable), competitive to substrate phosphoenolpyruvate
(2S)-2,7-bis(phosphonooxy)heptanoic acid
-
(2S)-2-(phosphonooxy)propanoic acid
-
mimicking phosphohemiketal 2 (instable), competitive to substrate phosphoenolpyruvate
(2Z)-3-phosphono-2-(trifluoromethyl)prop-2-enoic acid
-
trifluorinated phosphonate
(E)-2-methyl-3-phosphonoacrylic acid
-
most potent of the tested inhibitors mimicking intermediates in the reaction, vinyl phosphonate 4
(R)-phospholactate
-
(S)-phospholactate
-
1,10-phenanthroline
-
activity is restored by Fe2+ or Zn2+
2,3-bisphosphoglycerate
-
-
2-(phosphonomethyl)prop-2-enoic acid
-
mimics substrate phosphoenolpyruvate, and should be inert due to alkene structure but lacking an electron-donor, acts as competitive inhibitor
2-Methyl-DL-Trp
-
0.02 mM, 30% inhibition
2-phosphoglycerate
-
competitive with respect to phosphoenolpyruvate
3,4-dihydroxycinnamate
-
isoenzyme DS-Co
3-deoxy-D-arabino-heptonic acid 7-phosphate
-
-
3-deoxy-D-arabinoheptulosonate-7-phosphate oxime
3-deoxy-D-erythro-hept-2-ulosonate 7-phosphate
-
-
3-Methylphosphoenolpyruvate
-
-
3-Propylphosphoenolpyruvate
-
-
3-pyridine carboxyaldehyde
-
4-allylpyrocatechol
-
4-Methyl-DL-Trp
-
0.02 mM, 30% inhibition
5,5'-dithiobis(2-nitrobenzoate)
-
-
5-Fluoro-DL-Trp
-
0.02 mM, 56% inhibition
5-hydroxy-DL-Trp
-
0.02 mM, 10% inhibition
6-Methyl-DL-Trp
-
0.02 mM, 6% inhibition
7-Aza-DL-Trp
-
0.02 mM, 9% inhibition
7-Methyl-DL-Trp
-
0.02 mM, 14% inhibition
7-phospho-2-dehydro-3-deoxy-D-arabino-heptonate
allylpyrocatechol-3,4-diacetate
-
alpha-Methylphenylalanine
-
-
beta-2-Thienyl-D,L-Ala
-
-
beta-phenylserine
-
-
beta-Thienylalanine
-
-
chorismate
CN-
-
Tyr-sensitive isozyme, strong inhibition, reactivation by divalent cations only to a small extent
D-erythrose 4-phosphate
D-fructose 1,6-diphosphate
-
-
D-sedoheptulose 1,7-diphosphate
-
-
D-sedoheptulose 7-phosphate
-
-
diethyl dicarbonate
-
Phe-sensitive isozyme, pH-dependent, phosphoenolpyruvate protects wild-type and mutants H64G, H207G, H304G
dihydroxyphenylalanine
-
-
dipicolinic acid
DL-Dibromotryptophan
-
0.02 mM, 52% inhibition
DL-erythro-beta-Methyltryptophan
-
0.02 mM, 40% inhibition
DL-Homotryptophan
-
0.02 mM, 46% inhibition
eupalitin-3-O-galactoside
-
fosmidomycin
-
uncompetitive inhibitor, maximum level of inhibition after 10 min incubation, extent of inhibition dependent on the type of the metal cofactor, competitive inhibitor with respect to phosphoenolpyruvate
H2O2
DAHP synthase enzymes are inactivated by H2O2 in vitro and in vivo, H2O2 displaces the iron atom from the enzyme, only the Fe2+-metalloform of the enzyme can be inactivated by hydrogen peroxide or superoxide
Hg2+
-
complete inhibition at 1 mM
iodoacetamide
-
alkylation, abolishes the dependence on reducing agents
L-arogenate
-
isozyme DS-Mn, competitive against D-erythrose 4-phosphate, non-competitive against phosphoenolpyruvate
L-Phe
L-phenylalanine
L-Trp
L-tryptophan
L-Tyr
L-tyrosine
m-Chlorophenylalanine
-
-
m-Fluorophenylalanine
-
-
m-hydroxyphenylalanine
-
-
metal chelators
-
-
-
Mg2+
-
no inhibition of mutant C67L; wild-type and mutants
N-alpha-methyl-DL-Trp
-
0.02 mM, 60% inhibition
N-bromosuccinimide
-
-
N-ethylmaleimide
-
-
N-[Phosphomonomethyl]glycine
Na2SO4
-
slightly
o-chlorophenylalanine
-
-
o-Fluorophenylalanine
-
-
o-hydroxyphenylalanine
-
-
p-aminophenylalanine
-
-
p-chloromercuribenzoate
-
complete inhibition at 0.02 mM, reversible by cysteine
p-Fluorophenylalanine
-
-
p-hydroxymercuribenzoate
-
-
phenylalanine
phenylpyruvate
-
DAHP synthase-tyr
phosphate
phosphoenolpyruvate
pronounced substrate inhibition above 1 mM
prephenate
shikimate
-
1 mM, 3% residual activity
superoxide
displaces the iron atom from the enzyme, only the Fe2+-metalloform of the enzyme can be inactivated by hydrogen peroxide or superoxide. Superoxide stress promotes the mismetallation of DAHP synthase
tetraammonium (((carboxymethyl)[(2S,3R,4S)-2,3,4-trihydroxy-5-(phosphonatooxy)pentyl]amino)methyl)phosphonate
-
IC50: 0.0066 mM
Tetranitromethane
-
-
Trinitrobenzene sulfonate
-
-
tyrosine
vinyl phosphonate
-
[(1E)-7-bromo-2-carboxyhept-1-en-1-yl]phosphonate
-
inhibitor based on vinyl phosphonate, designed to fit into the binding sites of both phosphoenolpyruvate and D-erythrose 4-phosphate substrates simultaneously. Competitive with respect to phosphoenolpyruvate
[2-carboxy-7-(phosphonatooxy)hept-1-en-1-yl]phosphonate
-
inhibitor based on vinyl phosphonate ratio Z:E enantiomer 1:1. Inhibitor is designed to fit into the binding sites of both phosphoenolpyruvate and D-erythrose 4-phosphate substrates simultaneously. Competitive with respect to phosphoenolpyruvate
[2-carboxy-7-(phosphonatooxy)hept-2-en-1-yl]phosphonate
-
inhibitor based on allyl phosphonate, ratio Z:E enantiomer 7:3. Inhibitor is designed to fit into the binding sites of both phosphoenolpyruvate and D-erythrose 4-phosphate substrates simultaneously. Competitive with respect to phosphoenolpyruvate
additional information
-