Information on EC 1.3.1.19 - cis-1,2-dihydrobenzene-1,2-diol dehydrogenase

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The expected taxonomic range for this enzyme is: Proteobacteria

EC NUMBER
COMMENTARY hide
1.3.1.19
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RECOMMENDED NAME
GeneOntology No.
cis-1,2-dihydrobenzene-1,2-diol dehydrogenase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
cis-1,2-dihydrobenzene-1,2-diol + NAD+ = catechol + NADH + H+
show the reaction diagram
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
dehydrogenation
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oxidation
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redox reaction
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reduction
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
benzene degradation
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Benzoate degradation
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Chlorocyclohexane and chlorobenzene degradation
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Metabolic pathways
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Microbial metabolism in diverse environments
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Polycyclic aromatic hydrocarbon degradation
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Styrene degradation
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Toluene degradation
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toluene degradation to 2-oxopent-4-enoate (via toluene-cis-diol)
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SYSTEMATIC NAME
IUBMB Comments
cis-1,2-dihydrobenzene-1,2-diol:NAD+ oxidoreductase
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CAS REGISTRY NUMBER
COMMENTARY hide
51923-03-6
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
metabolism
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
1,2-propanediol + NAD+
propen-1,2-diol + NADH
show the reaction diagram
5-methyl-hex-4-ene-1,2-diol + NAD+
5-methyl-hex-1,4-diene-1,2-diol + NADH + H+
show the reaction diagram
7-methyl-oct-6-ene-1,2-diol + NAD+
7-methyl-oct-1,6-diene-1,2-diol + NADH + H+
show the reaction diagram
butane-1,2-diol + NAD+
but-1-ene-1,2-diol + NADH
show the reaction diagram
cis-1,2-cyclohexanediol + NAD+
cyclohex-1-ene-1,2-diol + NADH
show the reaction diagram
cis-1,2-dihydrobenzene-1,2-diol + NAD+
catechol + NADH
show the reaction diagram
cis-1,2-dihydrobenzene-3-bromo-(R,R)-1,2-diol + NAD+
3-bromocatechol + NADH
show the reaction diagram
cis-1,2-dihydrobenzene-3-chloro-(R,R)-1,2-diol + NAD+
3-chlorocatechol + NADH
show the reaction diagram
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22% of activity with cis-1,2-dihydrobenzene-1,2-diol
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?
cis-1,2-dihydrobenzene-3-fluoro-(R,R)-1,2-diol + NAD+
3-fluorocatechol + NADH
show the reaction diagram
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35% of activity with cis-1,2-dihydrobenzene-1,2-diol
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?
decane-1,2-diol + NAD+
dec-1-ene-1,2-diol + NADH
show the reaction diagram
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8% of activity with cis-1,2-dihydrobenzene-1,2-diol
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?
glycerol + NAD+
?
show the reaction diagram
isobutane-1,2-diol + NAD+
isobut-1-ene-1,2-diol + NADH
show the reaction diagram
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28% of activity with cis-1,2-dihydrobenzene-1,2-diol
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?
naphthalene-cis-1,2-dihydrodiol + NAD+
?
show the reaction diagram
nonane-1,2-diol + NAD+
non-1-ene-1,2-diol + NADH
show the reaction diagram
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15% of activity with cis-1,2-dihydrobenzene-1,2-diol
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?
propane-1,2-diol + NAD+
prop-1-ene-1,2-diol + NADH
show the reaction diagram
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36% of activity with cis-1,2-dihydrobenzene-1,2-diol
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?
trimethylbutane-1,2-diol + NAD+
trimethylbut-1-ene-1,2-diol + NADH
show the reaction diagram
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21% of activity with cis-1,2-dihydrobenzene-1,2-diol
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?
additional information
?
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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
cis-1,2-dihydrobenzene-1,2-diol + NAD+
catechol + NADH
show the reaction diagram
naphthalene-cis-1,2-dihydrodiol + NAD+
?
show the reaction diagram
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Fe2+
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optimum Fe2+ concentration 0.1 mM
additional information
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no metal ions requirement
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
1,10-phenanthroline
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p-chloromercuribenzoic acid
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
L-cysteine
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.01 - 0.286
cis-1,2-dihydrobenzene-1,2-diol
46
glycerol
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cosubstrate NAD+
0.0435 - 0.57
NAD+
0.066
naphthalene-cis-1,2-dihydrodiol
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pH 7.2, 45C
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.098
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crude enzyme extract, pH 7.2, 45C
5.1
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purified native enzyme, pH 7.2, 45C
19.1
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cis-1,2-dihydrobenzene-1,2-diol, NAD+
68
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glycerol, NAD+
153
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cis-1,2-dihydrobenzene-1,2-diol, NAD+
313
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cis-1,2-cyclohexanediol, NAD+
513
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1,2-propanediol, NAD+
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7.4
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with NAD+ as cofactor and Fe2+ ions, 25 mM potassium phosphate buffer
9
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with NAD+ as cofactor, 100 mM potassium carbonate buffer
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
5 - 9
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activity range
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
TEMPERATURE RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
5 - 60
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activity range
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
160000
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gel filtration
166000
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PAGE
220000
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gel filtration
440000
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ultracentrifugation
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
hexamer
homohexamer
tetramer
Crystallization/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
pH STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7.9
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in 25 mM-potassium phosphate buffer
390586
GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
dilution, 0-4C, sharp fall in activity in the first 5-10 h
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loss of activity by ammonium sulfate precipitation and subsequent dialysis, restored by Fe2+
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STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
0-4C or frozen at -22C, concentrated solution, several weeks
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enzyme activity is retained during purification and storage in 100 mM Tris-HCl buffer, pH 7.2, containing 5% ethanol
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less stable at 4C than at -20C, loss of activity at 4C gradually over a few days
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Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
dye-affinity chromatography and NAD+ agarose chromatography
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native enzyme from strain 26K by anion exchange and hydrophobic interaction chromatography
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Q-Sepharose, Superdex 200, Mono Q
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
gene bedD encoding cis-benzene dihydrodiol dehydrogenase on the natural plasmid pHMT112, expressed in Escherichia coli; sequenze similarity to glycerol dehydrogenase of Escherichia coli
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APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
analysis
synthesis