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Information on EC 1.3.1.28 - 2,3-dihydro-2,3-dihydroxybenzoate dehydrogenase for references in articles please use BRENDA:EC1.3.1.28
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EC Tree
The enzyme appears in viruses and cellular organisms
Synonyms
2,3-DHB dehydrogenase, 2,3-dihydro-2,3-dihydroxybenzoic acid dehydrogenase, cbxG, Cold shock protein CSI14, dehydrogenase, 2,3-dihydro-2,3-dihydroxybenzoate, EC 1.1.1.109, EntA,
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2,3-DHB dehydrogenase
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2,3-dihydro-2,3-dihydroxybenzoic acid dehydrogenase
Cold shock protein CSI14
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dehydrogenase, 2,3-dihydro-2,3-dihydroxybenzoate
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EC 1.1.1.109
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formerly
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2,3-dihydro-2,3-dihydroxybenzoic acid dehydrogenase
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2,3-dihydro-2,3-dihydroxybenzoic acid dehydrogenase
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EntA
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(2S,3S)-2,3-dihydro-2,3-dihydroxybenzoate + NAD+ = 2,3-dihydroxybenzoate + NADH + H+
(2S,3S)-2,3-dihydro-2,3-dihydroxybenzoate + NAD+ = 2,3-dihydroxybenzoate + NADH + H+
enzyme functions as an alcohol dehydrogenase which oxidizes the C3-hydroxylgroup of the substrate, the transient intermediate 2-hydroxy-3-oxo-4,6-cyclohexadiene-1-carboxylate undergoes rapid aromatization to give 2,3-dihydroxybenzoate
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(2S,3S)-2,3-dihydro-2,3-dihydroxybenzoate + NAD+ = 2,3-dihydroxybenzoate + NADH + H+
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(2S,3S)-2,3-dihydro-2,3-dihydroxybenzoate:NAD+ oxidoreductase
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(2S,3S)-2,3-dihydro-2,3-dihydroxybenzoate + NAD+
2,3-dihydroxybenzoate + NADH + H+
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2-cyclohexen-1-ol + NAD+
1-oxo-2-cyclohexene + NADH
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r
3-hydroxy-4-cyclohexene-1-carboxylate
3-oxo-4-cyclohexene-1-carboxylate + NADH
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reversible only with 3-keto compounds, not with 2-keto compounds
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r
4-isopropyl-2,3-dihydroxybenzoate + NAD+
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4-trifluoromethyl-2,3-dihydro-2,3-dihydroxybenzoate + NAD+
4-trifluoromethyl-2,3-dihydroxybenzoate + NADH
cis-1,3-cyclohexadiene-5,6-diol + NAD+
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r
cis-3-hydroxy-cyclohexane-1-carboxylate + NAD+
3-oxo-cyclohexane-1-carboxylate + NADH
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r
methyl-2,3-dihydro-3-hydroxybenzoate + NAD+
3-hydroxybenzoate + NADH
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r
methyl-3-hydroxy-1,4-cyclohexadien-1-carboxylate + NAD+
3-hydroxybenzoate + NADH
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r
trans-1,3-cyclohexadiene-5,6-diol + NAD+
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r
trans-2,3-dihydro-2,3-dihydroxybenzoate + NAD+
2,3-dihydroxybenzoate + NADH
trans-3-hydroxy-cyclohexane-1-carboxylate + NAD+
3-oxo-cyclohexane-1-carboxylate + NADH
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r
4-isopropyl-2,3-dihydroxybenzoate + NAD+
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4-isopropyl-2,3-dihydroxybenzoate + NAD+
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4-trifluoromethyl-2,3-dihydro-2,3-dihydroxybenzoate + NAD+
4-trifluoromethyl-2,3-dihydroxybenzoate + NADH
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low turnover
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4-trifluoromethyl-2,3-dihydro-2,3-dihydroxybenzoate + NAD+
4-trifluoromethyl-2,3-dihydroxybenzoate + NADH
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low turnover
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trans-2,3-dihydro-2,3-dihydroxybenzoate + NAD+
2,3-dihydroxybenzoate + NADH
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ir
trans-2,3-dihydro-2,3-dihydroxybenzoate + NAD+
2,3-dihydroxybenzoate + NADH
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genetic results suggest that the enzyme may also have isochorismate synthase activity
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(2S,3S)-2,3-dihydro-2,3-dihydroxybenzoate + NAD+
2,3-dihydroxybenzoate + NADH + H+
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NAD+
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absolutely required
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4-Trifluoromethyl-2,3-dihydro-2,3-dihydroxybenzoate
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competitive inhibition
cis-2-hydroxy-3-cyclohexen-1-carboxylate
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cis-2-hydroxycyclohexane-1-carboxylate
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trans-2-hydroxycyclohexane-1-carboxylate
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0.3
2,3-Dihydro-2,3-dihydroxybenzoate
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83.3
2-Cyclohexen-1-ol
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0.017
4-isopropyl-2,3-dihydroxybenzoate
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168
cis-3,5-cyclohexadiene-1,2-diol
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2.8
cis-3-hydroxy-4-cyclohexene-1-carboxylate
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4.1
cis-3-hydroxycyclohexane-1-carboxylic acid
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0.26
methyl 2,3-dihydro-2,3-dihydroxybenzoate
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1.7
methyl-3-hydroxy-1,4-cyclohexadiene-1-carboxylate
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0.037
NAD+
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substrate 4-isopropyl-2,3-dihydroxybenzoate
16.5
trans-3,5-cyclohexadiene-1,2-diol
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1.9
trans-3-hydroxy-2-cyclohexene-1-carboxylate
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25.2
trans-3-hydroxycyclohexane-1-carboxylic acid
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25.3
2,3-dihydo-2,3-dihydroxybenzoate
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16.7
cis-3,5-cyclohexadiene-1,2-diol
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cis-3-hydroxy-4-cyclohexene-1-carboxylate
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5
cis-3-hydroxycyclohexane-1-carboxylic acid
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17.5
methyl 2,3-dihydro-2,3-dihydroxybenzoate
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3
methyl-3-hydroxy-1,4-cyclohexadiene-1-carboxylate
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92.5
trans-2,3-dihydro-2,3-dihydroxy-benzoate
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1
trans-3,5-cyclohexadiene-1,2-diol
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5
trans-3-hydroxy-2-cyclohexene-1-carboxylate
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0.733
trans-3-hydroxycyclohexane-1-carboxylic acid
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0.012
4-Trifluoromethyl-2,3-dihydro-2,3-dihydroxybenzoate
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1.4
cis-2-hydroxy-3-cyclohexen-1-carboxylate
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3.3
cis-2-hydroxycyclohexane-1-carboxylate
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2.3
trans-2-hydroxycyclohexane-1-carboxylate
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0.0046
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enzyme activity in crude extracts of cells grown in the presence of 0.002 mM iron, enzyme is repressed by high iron concentrations
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brenda
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brenda
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brenda
JT strains
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JT strains
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brenda
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brenda
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Escherichia coli (strain K12)
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26000
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x * 26000, deduced from nucleotide sequence
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?
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x * 26000, deduced from nucleotide sequence
octamer
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8 * 26249-26253, deduced from nucleotide sequence
additional information
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enzyme can form a specific complex with 2,3-dihydroxybenzoate-AMP ligase EntE. Cross-linked product with a molecular mass of more than 250 kDa, suggesting a complex stoichiometry of one EntA tetramer and four EntE monomers. Addition of a 4-fold excess of EntA to an EntE assay mixture results in a 6fold stimulation of EntE activity; enzyme undergoes concentration-dependent dimer-tetramer self-association with a KD value of 12.3 microM, analytical ultracentrifugation
tetramer
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to 2.0 A resolution by hanging-drop method
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unstable after chromatography on DEAE cellulose
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by two IMAC chromatography steps
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into vector pET15b and expressed in Escherichia coli BL21(DE3)
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Young, I.G.; Gibson, F.
Regulation of the enzymes involved in the biosynthesis of 2,3-dihydroxybenzoic acid in Aerobacter aerogenes and Escherichia coli
Biochim. Biophys. Acta
177
401-411
1969
Klebsiella aerogenes
brenda
Nahlik, M.S.; Fleming, T.P.; McIntosh, M.A.
Cluster of genes controlling synthesis and activation of 2,3-dihydroxybenzoic acid in production of enterobactin in Escherichia coli
J. Bacteriol.
169
4163-4170
1987
Escherichia coli
brenda
Sakaitani, M.; Rusnak, F.; Quinn, N.R.; Tu, C.; Frigo, R.B.; Berchtold, G.A.; Walsh, C.T.
Mechanistic studies on trans-2,3-dihydro-2,3-dihydroxybenzoate dehydrogenase (Ent A) in the biosynthesis of the iron chelator enterobactin
Biochemistry
29
6789-6798
1990
Escherichia coli
brenda
Liu, J.; Duncan, K.; Walsh, C.T
Nucleotide sequence of a cluster of Escherichia coli enterobactin biosynthesis genes: identification of entA and purification of its product 2,3-dihydro-2,3-dihydroxybenzoate dehydrogenase
J. Bacteriol.
171
791-798
1989
Escherichia coli
brenda
Engesser, K.H.; Rubio, M.A.; Ribbons, D.W.
Bacterial metabolism of side chain fluorinated aromatics: cometabolism of 4-trifluoromethyl(TFM)-benzoate by 4-isopropylbenzoate grown Pseudomonas putida JT strains
Arch. Microbiol.
149
198-206
1988
Pseudomonas putida, Pseudomonas putida JT
brenda
Schrodt Nahlik, M.; Brickman, T.J.; Ozenberger, B.A.; McIntosh, M.A.
Nucleotide sequence and transcriptional organization of the Escherichia coli enterobactin biosynthesis cistrons entB and entA
J. Bacteriol.
171
784-790
1989
Escherichia coli
brenda
Sundlov, J.A.; Garringer, J.A.; Carney, J.M.; Reger, A.S.; Drake, E.J.; Duax, W.L.; Gulick, A.M.
Determination of the crystal structure of EntA, a 2,3-dihydro-2,3-dihydroxybenzoic acid dehydrogenase from Escherichia coli
Acta Crystallogr. Sect. D
D62
734-740
2006
Escherichia coli, Escherichia coli JM109
brenda
Khalil, S.; Pawelek, P.D.
Enzymatic adenylation of 2,3-dihydroxybenzoate is enhanced by a protein-protein interaction between Escherichia coli 2,3-dihydro-2,3-dihydroxybenzoate dehydrogenase (EntA) and 2,3-dihydroxybenzoate-AMP ligase (EntE)
Biochemistry
50
533-545
2011
Escherichia coli
brenda
Losada, A.A.; Cano-Prieto, C.; Garcia-Salcedo, R.; Brana, A.F.; Mendez, C.; Salas, J.A.; Olano, C.
Caboxamycin biosynthesis pathway and identification of novel benzoxazoles produced by cross-talk in Streptomyces sp. NTK 937
Microb. Biotechnol.
10
873-885
2017
Streptomyces sp. NTK 937
brenda
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1.3.1.28 2,3-dihydro-2,3-dihydroxybenzoate dehydrogenase
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