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Information on EC 1.14.13.24 - 3-hydroxybenzoate 6-monooxygenase
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1.14.13.24 3-hydroxybenzoate 6-monooxygenaseIUBMB Comments
A flavoprotein (FAD). Acts also on a number of analogues of 3-hydroxybenzoate substituted in the 2, 4, 5 and 6 positions; NADPH can act instead of NADH, but more slowly.
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Word Map
- 1.14.13.24
- gentisate
- flavoprotein
- flavin
- fad
- rhodococcus
- salicylate
- hydroxylases
- jostii
- 2,5-dihydroxybenzoate
- maleylpyruvate
-
para-hydroxylation
- alcaligenes
-
nadh-dependent
-
flavin-dependent
-
ncimb
-
near-uv
- fumarylpyruvate
-
nadh-specific
- p-hydroxybenzoate
-
regioselective
The expected taxonomic range for this enzyme is: Bacteria, Eukaryota
Synonyms
3-hydroxybenzoate 6-hydroxylase, 3hb6h, 3-hydroxybenzoate-6-hydroxylase, 3-hba-6-hydroxylase, ncgl2923, mnx2p, 3-hydroxybenzoate 6-monooxygenase, m-hydroxybenzoate 6-hydroxylase, 3-hydroxybenzoic acid-6-hydroxylase, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
3-HBA-6-hydroxylase
-
-
-
-
3-hydroxybenzoate 6-hydroxylase
3-hydroxybenzoate-6-hydroxylase
3-hydroxybenzoic acid-6-hydroxylase
-
-
-
-
3HB6H
m-hydroxybenzoate 6-hydroxylase
-
-
-
-
MNX2
Mnx2p
NarX
Ncgl2923
oxygenase, 3-hydroxybenzoate 6-mono-
-
-
-
-
XlnD
3-hydroxybenzoate 6-hydroxylase
-
-
-
-
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
3-hydroxybenzoate + NADH + H+ + O2 = 2,5-dihydroxybenzoate + NAD+ + H2O
mechanism
-
3-hydroxybenzoate + NADH + H+ + O2 = 2,5-dihydroxybenzoate + NAD+ + H2O
A-stereospecificity
-
3-hydroxybenzoate + NADH + H+ + O2 = 2,5-dihydroxybenzoate + NAD+ + H2O
Arg169 is essential for catalytic activity
3-hydroxybenzoate + NADH + H+ + O2 = 2,5-dihydroxybenzoate + NAD+ + H2O
catalytic mechanism involving FAD, overview
3-hydroxybenzoate + NADH + H+ + O2 = 2,5-dihydroxybenzoate + NAD+ + H2O
catalytic mechanism involving FAD, overview
-
-
3-hydroxybenzoate + NADH + H+ + O2 = 2,5-dihydroxybenzoate + NAD+ + H2O
A-stereospecificity
-
-
3-hydroxybenzoate + NADH + H+ + O2 = 2,5-dihydroxybenzoate + NAD+ + H2O
-
-
-
-
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
oxidation
-
-
-
-
redox reaction
-
-
-
-
reduction
-
-
-
-
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PATHWAY SOURCE
PATHWAYS
-
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SYSTEMATIC NAME
IUBMB Comments
3-hydroxybenzoate,NADH:oxygen oxidoreductase (6-hydroxylating)
A flavoprotein (FAD). Acts also on a number of analogues of 3-hydroxybenzoate substituted in the 2, 4, 5 and 6 positions; NADPH can act instead of NADH, but more slowly.
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CAS REGISTRY NUMBER
COMMENTARY
51570-26-4
-
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
2,3,4-trihydroxybenzoate + NADH + H+ + O2
2,3,4,6-tetrahydroxybenzoate + NAD+ + H2O
-
-
-
-
?
2,3-dihydroxybenzoate + NADH + H+ + O2
2,3,6-trihydroxybenzoate + NAD+ + H2O
-
-
-
-
?
3,5-dihydroxybenzoate + NADH + H+ + O2
2,3,5,6-tetrahydroxybenzoate + NAD+ + H2O
-
-
-
-
?
3-hydroxy-3-methylbenzoate + NAD(P)H + O2
2,5-dihydroxy-3-methylbenzoate + NAD(P)+ + H2O
-
-
-
?
3-hydroxy-4-aminobenzoate + NADH + H+ + O2
4-amino-2,5-dihydroxybenzoate + NAD+ + H2O
-
-
-
-
?
3-hydroxy-4-methoxybenzoate + NADH + H+ + O2
4-methoxy-2,5-dihydroxybenzoate + NAD+ + H2O
-
-
-
-
?
3-hydroxy-4-methylbenzoate + NAD(P)H + O2
2,5-dihydroxy-4-methylbenzoate + NAD(P)+ + H2O
the substrate is an intermediate in the degradation of 2,5-xylenol, higher activity with the recombinant His-tagged enzyme compared to the native enzyme
-
-
?
3-hydroxy-4-methylbenzoate + NADH + H+ + O2
4-methyl-2,5-dihydroxybenzoate + NAD+ + H2O
-
-
-
-
?
3-hydroxy-5-methylbenzoate + NAD(P)H + O2
2,5-dihydroxy-3-methylbenzoate + NAD(P)+ + H2O
the substrate is an intermediate in the degradation of 3,5-xylenol, higher activity with the recombinant His-tagged enzyme compared to the native enzyme, preferred substrate
-
-
?
4-fluoro-3-hydroxybenzoate + NADH + O2
4-fluoro-2,5-dihydroxybenzoate + NAD+ + H2O
-
36% of the reaction with 3-hydroxybenzoate
-
?
2,3-dihydroxybenzoate + NADH + O2
2,3,5-trihydroxybenzoate + NAD+ + H2O
-
10.5% of the reaction with 3-hydroxybenzoate
-
?
2,3-dihydroxybenzoate + NADH + O2
2,3,5-trihydroxybenzoate + NAD+ + H2O
-
10.5% of the reaction with 3-hydroxybenzoate
-
?
3,4-dihydroxybenzoate + NADH + O2
2,4,5-trihydroxybenzoate + NAD+ + H2O
-
9% of the reaction with 3-hydroxybenzoate
-
?
3,4-dihydroxybenzoate + NADH + O2
2,4,5-trihydroxybenzoate + NAD+ + H2O
-
9% of the reaction with 3-hydroxybenzoate
-
?
3,5-dihydroxybenzoate + NADH + O2
2,3,5-trihydroxybenzoate + NAD+ + H2O
-
7% of the reaction with 3-hydroxybenzoate
-
?
3,5-dihydroxybenzoate + NADH + O2
2,3,5-trihydroxybenzoate + NAD+ + H2O
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7% of the reaction with 3-hydroxybenzoate
-
?
3-hydroxy-5-methylbenzoate + NADH + O2
2,5-dihydroxy-3-methylbenzoate + NAD+ + H2O
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31% of the reaction with 3-hydroxybenzoate
-
?
3-hydroxy-5-methylbenzoate + NADH + O2
2,5-dihydroxy-3-methylbenzoate + NAD+ + H2O
-
31% of the reaction with 3-hydroxybenzoate
-
?
3-hydroxybenzoate + NAD(P)H + H+ + O2
gentisate + NAD(P)+ + H2O
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-
i.e. 2,5-dihydroxybenzoate
-
?
3-hydroxybenzoate + NAD(P)H + H+ + O2
gentisate + NAD(P)+ + H2O
-
the small catabolic gene cluster nagR2-orf2I''KL in strain CJ2 may be multifunctional and is essential for the degradation of 3-hydroxybenzoate
i.e. 2,5-dihydroxybenzoate
-
?
3-hydroxybenzoate + NAD(P)H + O2
2,5-dihydroxybenzoate + NAD(P)+ + H2O
-
i.e. gentisate
-
?
3-hydroxybenzoate + NAD(P)H + O2
2,5-dihydroxybenzoate + NAD(P)+ + H2O
the enzyme is involved in the degradation of 2,5-xylenol and 3,5-xylenol via the gentisate pathway, overview
-
-
?
3-hydroxybenzoate + NAD(P)H + O2
2,5-dihydroxybenzoate + NAD(P)+ + H2O
-
i.e. gentisate
-
?
3-hydroxybenzoate + NAD(P)H + O2
2,5-dihydroxybenzoate + NAD(P)+ + H2O
the enzyme is involved in the degradation of 2,5-xylenol and 3,5-xylenol via the gentisate pathway, overview
-
-
?
3-hydroxybenzoate + NADH + H+ + O2
2,5-dihydroxybenzoate + NAD+ + H2O
-
i.e. gentisate
-
?
3-hydroxybenzoate + NADH + H+ + O2
2,5-dihydroxybenzoate + NAD+ + H2O
-
i.e. gentisate
-
?
3-hydroxybenzoate + NADH + H+ + O2
2,5-dihydroxybenzoate + NAD+ + H2O
-
-
-
-
?
3-hydroxybenzoate + NADH + H+ + O2
2,5-dihydroxybenzoate + NAD+ + H2O
-
-
-
-
r
3-hydroxybenzoate + NADH + H+ + O2
2,5-dihydroxybenzoate + NAD+ + H2O
-
-
-
-
?
3-hydroxybenzoate + NADH + H+ + O2
2,5-dihydroxybenzoate + NAD+ + H2O
-
-
-
?
3-hydroxybenzoate + NADH + H+ + O2
2,5-dihydroxybenzoate + NAD+ + H2O
-
the enzyme clearly prefers NADH as external electron donor over NADPH
-
-
?
3-hydroxybenzoate + NADH + H+ + O2
2,5-dihydroxybenzoate + NAD+ + H2O
-
-
-
?
3-hydroxybenzoate + NADH + H+ + O2
2,5-dihydroxybenzoate + NAD+ + H2O
NarX shows activity on 3-hydroxybenzoate rather than on salicylate
-
-
?
3-hydroxybenzoate + NADH + H+ + O2
2,5-dihydroxybenzoate + NAD+ + H2O
-
-
-
?
3-hydroxybenzoate + NADH + H+ + O2
2,5-dihydroxybenzoate + NAD+ + H2O
NarX shows activity on 3-hydroxybenzoate rather than on salicylate
-
-
?
3-hydroxybenzoate + NADH + O2
2,5-dihydroxybenzoate + NAD+ + H2O
-
-
-
?
3-hydroxybenzoate + NADH + O2
2,5-dihydroxybenzoate + NAD+ + H2O
-
-
-
?
3-hydroxybenzoate + NADH + O2
2,5-dihydroxybenzoate + NAD+ + H2O
-
i.e. gentisate
-
?
3-hydroxybenzoate + NADH + O2
2,5-dihydroxybenzoate + NAD+ + H2O
-
-
-
-
?
3-hydroxybenzoate + NADH + O2
2,5-dihydroxybenzoate + NAD+ + H2O
-
-
-
-
?
3-hydroxybenzoate + NADH + O2
2,5-dihydroxybenzoate + NAD+ + H2O
-
-
-
-
?
3-hydroxybenzoate + NADH + O2
2,5-dihydroxybenzoate + NAD+ + H2O
-
strictly specific for 3-hydroxybenzoate
-
-
?
3-hydroxybenzoate + NADH + O2
2,5-dihydroxybenzoate + NAD+ + H2O
-
key role in metabolism of aromatic compounds
-
-
?
3-hydroxybenzoate + NADH + O2
2,5-dihydroxybenzoate + NAD+ + H2O
-
-
-
-
?
3-hydroxybenzoate + NADH + O2
2,5-dihydroxybenzoate + NAD+ + H2O
-
-
-
-
?
3-hydroxybenzoate + NADPH + H+ + O2
2,5-dihydroxybenzoate + NADP+ + H2O
-
-
-
-
r
3-hydroxybenzoate + NADPH + H+ + O2
2,5-dihydroxybenzoate + NADP+ + H2O
-
-
-
-
?
3-hydroxybenzoate + NADPH + H+ + O2
2,5-dihydroxybenzoate + NADP+ + H2O
-
-
-
-
?
3-hydroxybenzoate + NADPH + H+ + O2
2,5-dihydroxybenzoate + NADP+ + H2O
-
i.e. gentisate
-
?
3-hydroxybenzoate + NADPH + H+ + O2
2,5-dihydroxybenzoate + NADP+ + H2O
-
i.e. gentisate
-
?
3-hydroxybenzoate + NADPH + H+ + O2
2,5-dihydroxybenzoate + NADP+ + H2O
-
-
-
-
r
3-hydroxybenzoate + NADPH + H+ + O2
2,5-dihydroxybenzoate + NADP+ + H2O
-
-
-
-
r
3-hydroxybenzoate + NADPH + H+ + O2
2,5-dihydroxybenzoate + NADP+ + H2O
-
-
-
-
r
3-hydroxybenzoate + NADPH + H+ + O2
2,5-dihydroxybenzoate + NADP+ + H2O
-
the enzyme clearly prefers NADH as external electron donor over NADPH
-
-
?
3-hydroxybenzoate + NADPH + H+ + O2
2,5-dihydroxybenzoate + NADP+ + H2O
-
-
-
?
3-hydroxybenzoate + NADPH + H+ + O2
2,5-dihydroxybenzoate + NADP+ + H2O
-
-
-
?
additional information
?
-
-
acts also on a number of analogs of 3-hydroxybenzoate substituted in the 2, 3, 5 and 6 positions
-
-
?
additional information
?
-
-
the enzyme shows no salicylate 5-hydroxylase activity
-
-
?
additional information
?
-
degradation of 2,5-xylenol and 3,5-xylenol in strain P25X depends on isozyme I, not isozyme II
-
-
?
additional information
?
-
degradation of 2,5-xylenol and 3,5-xylenol in strain P25X depends on isozyme I, not isozyme II
-
-
?
additional information
?
-
the purified H6-NarX protein shows no detectable activity against the 3HBA structural analogues, including 2-hydroxybenzoate, i.e. salicylate, 4-hydroxybenzoate, or 4-substituted derivatives (4-CH3, 4-NH2, and 4-NO2) of 3-hydroxybenzoate
-
-
?
additional information
?
-
-
the purified H6-NarX protein shows no detectable activity against the 3HBA structural analogues, including 2-hydroxybenzoate, i.e. salicylate, 4-hydroxybenzoate, or 4-substituted derivatives (4-CH3, 4-NH2, and 4-NO2) of 3-hydroxybenzoate
-
-
?
additional information
?
-
the purified H6-NarX protein shows no detectable activity against the 3HBA structural analogues, including 2-hydroxybenzoate, i.e. salicylate, 4-hydroxybenzoate, or 4-substituted derivatives (4-CH3, 4-NH2, and 4-NO2) of 3-hydroxybenzoate
-
-
?
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NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
3-hydroxybenzoate + NAD(P)H + H+ + O2
gentisate + NAD(P)+ + H2O
-
the small catabolic gene cluster nagR2-orf2I''KL in strain CJ2 may be multifunctional and is essential for the degradation of 3-hydroxybenzoate
i.e. 2,5-dihydroxybenzoate
-
?
3-hydroxybenzoate + NAD(P)H + O2
2,5-dihydroxybenzoate + NAD(P)+ + H2O
the enzyme is involved in the degradation of 2,5-xylenol and 3,5-xylenol via the gentisate pathway, overview
-
-
?
3-hydroxybenzoate + NAD(P)H + O2
2,5-dihydroxybenzoate + NAD(P)+ + H2O
the enzyme is involved in the degradation of 2,5-xylenol and 3,5-xylenol via the gentisate pathway, overview
-
-
?
3-hydroxybenzoate + NADH + H+ + O2
2,5-dihydroxybenzoate + NAD+ + H2O
-
i.e. gentisate
-
?
3-hydroxybenzoate + NADH + H+ + O2
2,5-dihydroxybenzoate + NAD+ + H2O
-
i.e. gentisate
-
?
3-hydroxybenzoate + NADH + H+ + O2
2,5-dihydroxybenzoate + NAD+ + H2O
-
-
-
-
?
3-hydroxybenzoate + NADH + H+ + O2
2,5-dihydroxybenzoate + NAD+ + H2O
-
-
-
-
?
3-hydroxybenzoate + NADH + H+ + O2
2,5-dihydroxybenzoate + NAD+ + H2O
-
-
-
?
3-hydroxybenzoate + NADH + H+ + O2
2,5-dihydroxybenzoate + NAD+ + H2O
-
the enzyme clearly prefers NADH as external electron donor over NADPH
-
-
?
3-hydroxybenzoate + NADH + H+ + O2
2,5-dihydroxybenzoate + NAD+ + H2O
NarX shows activity on 3-hydroxybenzoate rather than on salicylate
-
-
?
3-hydroxybenzoate + NADH + H+ + O2
2,5-dihydroxybenzoate + NAD+ + H2O
NarX shows activity on 3-hydroxybenzoate rather than on salicylate
-
-
?
3-hydroxybenzoate + NADH + O2
2,5-dihydroxybenzoate + NAD+ + H2O
-
i.e. gentisate
-
?
3-hydroxybenzoate + NADH + O2
2,5-dihydroxybenzoate + NAD+ + H2O
-
key role in metabolism of aromatic compounds
-
-
?
3-hydroxybenzoate + NADPH + H+ + O2
2,5-dihydroxybenzoate + NADP+ + H2O
-
-
-
-
?
3-hydroxybenzoate + NADPH + H+ + O2
2,5-dihydroxybenzoate + NADP+ + H2O
-
-
-
-
?
3-hydroxybenzoate + NADPH + H+ + O2
2,5-dihydroxybenzoate + NADP+ + H2O
-
i.e. gentisate
-
?
3-hydroxybenzoate + NADPH + H+ + O2
2,5-dihydroxybenzoate + NADP+ + H2O
-
i.e. gentisate
-
?
3-hydroxybenzoate + NADPH + H+ + O2
2,5-dihydroxybenzoate + NADP+ + H2O
-
-
-
?
3-hydroxybenzoate + NADPH + H+ + O2
2,5-dihydroxybenzoate + NADP+ + H2O
-
-
-
?
additional information
?
-
degradation of 2,5-xylenol and 3,5-xylenol in strain P25X depends on isozyme I, not isozyme II
-
-
?
additional information
?
-
degradation of 2,5-xylenol and 3,5-xylenol in strain P25X depends on isozyme I, not isozyme II
-
-
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
FAD
-
1 mol FAD per mol enzyme, exogenous addition of FAD required to regenerate oxidized FAD during catalysis
FAD
3fold activation at 0.015 mM. Sequence analysis of FAD/NADPH-binding domain of Ncgl2923, overview
FAD
-
residues 305, 306 and 308 are important for FAD binding. FAD concentration in the purified 3HB6H (0.29 mM) is 0.30 mM, and FAD/enzyme ratio is 1.02/0.05 determined by HPLC analysis
NADH
XlnD can utilize either NADH or NADPH as the electron donor, NADH is preferred
NADPH
XlnD can utilize either NADH or NADPH as the electron donor, NADH is preferred
additional information
the enzyme harbors a phospholipid ligand. The purified enzyme obtained from expressing the gene encoding 3HB6H from Rhodococcus jostii RHA1 in the host Escherichia coli contains a mixture of phosphatidylglycerol and phosphatidylethanolamine, which are the major constituents of the cytoplasmic membrane of Escherichia coli. The enzyme that is produced in the host Rhodococcus jostii RHA#2 by employing a newly developed actinomycete expression system, contains phosphatidylinositol, which is a specific constituent of actinomycete membranes. The lipid cofactor stabilizes monomer-monomer contact
-
additional information
-
the enzyme harbors a phospholipid ligand. The purified enzyme obtained from expressing the gene encoding 3HB6H from Rhodococcus jostii RHA1 in the host Escherichia coli contains a mixture of phosphatidylglycerol and phosphatidylethanolamine, which are the major constituents of the cytoplasmic membrane of Escherichia coli. The enzyme that is produced in the host Rhodococcus jostii RHA#2 by employing a newly developed actinomycete expression system, contains phosphatidylinositol, which is a specific constituent of actinomycete membranes. The lipid cofactor stabilizes monomer-monomer contact
-
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
additional information
additional information
-
enzyme activity is highest without salinity and metal salts. Ca2+ and Mn2+ have a poor effect on enzyme activity at 0.5 mM. With salinity ranging from 0 to 85.56 mM, the increase in salinity clearly causes decreased enzyme activity, 3% activity remaining at 85.56 mM salinity
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
Cu2+
-
85% inhibition at 0.01 mM, inhibition can be reversed by thiol reagents
diethylpyrocarbonate
-
80% loss of activity after 12 min at 0.1 mM, pseudo-first-order kinetics, substrate protects, 0.1 M hydroxylamine restores 75-85% of enzyme activity
Hg2+
-
85% inhibition at 0.01 mM, inhibition can be reversed by thiol reagents
N-bromosuccinimide
-
85-90% loss of activity at 0.04 mM, substrate protects, 10 mM N-acetylimidazole restores 85-90% of enzyme activity
Phenylglyoxal
-
70% loss of activity after 30 min at 0.5 mM, dialysis results in recovery of the enzyme, preincubation with the substrate causes significant protection
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
2,5-Dihydroxybenzoate
-
i.e. gentisate, strongly stimulates the NADH oxidase activity of the enzyme
additional information
isozyme II is strictly inducible by specific aromatic substrates
-
additional information
-
enzyme activity is not stimulated by salicylate
-
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE