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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The enzyme appears in viruses and cellular organisms

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EC NUMBER
COMMENTARY hide
1.3.1.28
-
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RECOMMENDED NAME
GeneOntology No.
2,3-dihydro-2,3-dihydroxybenzoate dehydrogenase
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REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
(2S,3S)-2,3-dihydro-2,3-dihydroxybenzoate + NAD+ = 2,3-dihydroxybenzoate + NADH + H+
show the reaction diagram
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
oxidation
-
-
-
-
redox reaction
-
-
-
-
reduction
-
-
-
-
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
2,3-dihydroxybenzoate biosynthesis
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enterobactin biosynthesis
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Biosynthesis of siderophore group nonribosomal peptides
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-
Biosynthesis of secondary metabolites
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Biosynthesis of antibiotics
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-
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SYSTEMATIC NAME
IUBMB Comments
(2S,3S)-2,3-dihydro-2,3-dihydroxybenzoate:NAD+ oxidoreductase
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CAS REGISTRY NUMBER
COMMENTARY hide
37250-40-1
-
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
JT strains
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Manually annotated by BRENDA team
JT strains
-
-
Manually annotated by BRENDA team
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SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(2S,3S)-2,3-dihydro-2,3-dihydroxybenzoate + NAD+
2,3-dihydroxybenzoate + NADH + H+
show the reaction diagram
-
-
-
-
?
2-cyclohexen-1-ol + NAD+
1-oxo-2-cyclohexene + NADH
show the reaction diagram
-
-
-
r
3-hydroxy-4-cyclohexene-1-carboxylate
3-oxo-4-cyclohexene-1-carboxylate + NADH
show the reaction diagram
-
reversible only with 3-keto compounds, not with 2-keto compounds
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r
4-isopropyl-2,3-dihydroxybenzoate + NAD+
?
show the reaction diagram
4-trifluoromethyl-2,3-dihydro-2,3-dihydroxybenzoate + NAD+
4-trifluoromethyl-2,3-dihydroxybenzoate + NADH
show the reaction diagram
cis-1,3-cyclohexadiene-5,6-diol + NAD+
?
show the reaction diagram
-
-
-
-
r
cis-3-hydroxy-cyclohexane-1-carboxylate + NAD+
3-oxo-cyclohexane-1-carboxylate + NADH
show the reaction diagram
-
-
-
r
methyl-2,3-dihydro-3-hydroxybenzoate + NAD+
3-hydroxybenzoate + NADH
show the reaction diagram
-
-
-
r
methyl-3-hydroxy-1,4-cyclohexadien-1-carboxylate + NAD+
3-hydroxybenzoate + NADH
show the reaction diagram
-
-
-
r
trans-1,3-cyclohexadiene-5,6-diol + NAD+
?
show the reaction diagram
-
-
-
-
r
trans-2,3-dihydro-2,3-dihydroxybenzoate + NAD+
2,3-dihydroxybenzoate + NADH
show the reaction diagram
trans-3-hydroxy-cyclohexane-1-carboxylate + NAD+
3-oxo-cyclohexane-1-carboxylate + NADH
show the reaction diagram
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-
-
r
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NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
(2S,3S)-2,3-dihydro-2,3-dihydroxybenzoate + NAD+
2,3-dihydroxybenzoate + NADH + H+
show the reaction diagram
-
-
-
-
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
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INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
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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-
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
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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-
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
25.3
2,3-dihydo-2,3-dihydroxybenzoate
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-
1
2-Cyclohexen-1-ol
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-
16.7
cis-3,5-cyclohexadiene-1,2-diol
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-
23
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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-
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Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
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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-
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.0046
-
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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PDB
SCOP
CATH
UNIPROT
ORGANISM
P15047
Escherichia coli (strain K12);
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
26000
-
x * 26000, deduced from nucleotide sequence
210000
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gel filtration
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SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
?
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x * 26000, deduced from nucleotide sequence
octamer
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8 * 26249-26253, deduced from nucleotide sequence
tetramer
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
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Crystallization/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
to 2.0 A resolution by hanging-drop method
-
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GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
unstable after chromatography on DEAE cellulose
-
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Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
by two IMAC chromatography steps
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
into vector pET15b and expressed in Escherichia coli BL21(DE3)
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Show AA Sequence (845 entries)
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LINKS TO OTHER DATABASES (specific for EC-Number 1.3.1.28)
ExplorEnz
ExPASy
KEGG
MetaCyc
SABIO-RK
NCBI: PubMed, Protein, Nucleotide, Structure, Genome, OMIM
IUBMB Enzyme Nomenclature
PROSITE Database of protein families and domains
InterPro (database of protein families, domains and functional sites)