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
1.3.1.19
-
RECOMMENDED NAME
GeneOntology No.
cis-1,2-dihydrobenzene-1,2-diol dehydrogenase
REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
cis-1,2-dihydrobenzene-1,2-diol + NAD+ = catechol + NADH + H+
show the reaction diagram
-
-
-
-
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
dehydrogenation
-
-
-
-
oxidation
-
-
-
-
redox reaction
-
-
-
-
reduction
-
-
-
-
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
benzene degradation
-
-
Benzoate degradation
-
-
Chlorocyclohexane and chlorobenzene degradation
-
-
Metabolic pathways
-
-
Microbial metabolism in diverse environments
-
-
Polycyclic aromatic hydrocarbon degradation
-
-
Styrene degradation
-
-
Toluene degradation
-
-
toluene degradation to 2-oxopent-4-enoate (via toluene-cis-diol)
-
-
SYSTEMATIC NAME
IUBMB Comments
cis-1,2-dihydrobenzene-1,2-diol:NAD+ oxidoreductase
-
SYNONYMS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
cis-1,2-dihydrocyclohexa-3,5-diene oxidoreductase
-
-
cis-benzene dihydrodiol dehydrogenase
-
-
cis-benzene dihydrodiol dehydrogenase
-
bedD enzyme
cis-benzene dihydrodiol dehydrogenase
Pseudomonas putida ML2
-
; bedD enzyme
-
cis-benzene glycol dehydrogenase
-
-
cis-benzene glycol dehydrogenase
Pseudomonas putida ML2
-
-
-
naphthalene cis-1,2-dihydrodiol dehydrogenase
-
-
naphthalene cis-1,2-dihydrodiol dehydrogenase
Pseudomonas fluorescens 26K
-
-
-
NDDH
Pseudomonas fluorescens 26K
-
-
-
CAS REGISTRY NUMBER
COMMENTARY
51923-03-6
-
ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
Pseudomonas fluorescens 26K
-
-
-
Manually annotated by BRENDA team
Pseudomonas fluorescens N3
-
-
-
Manually annotated by BRENDA team
biotype B
-
-
Manually annotated by BRENDA team
Pseudomonas putida ML2
ML2
-
-
Manually annotated by BRENDA team
Pseudomonas putida ML2
strain ML2
-
-
Manually annotated by BRENDA team
Pseudomonas putida MST
-
-
-
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
metabolism
-
the enzyme is involved in the metabolism and degradation of naphthalene
metabolism
Pseudomonas fluorescens 26K
-
the enzyme is involved in the metabolism and degradation of naphthalene
-
SUBSTRATE
PRODUCT                      
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
LITERATURE
(Substrate)
COMMENTARY
(Product)
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
1,2-propanediol + NAD+
propen-1,2-diol + NADH
show the reaction diagram
-
-
-
-
?
1,2-propanediol + NAD+
propen-1,2-diol + NADH
show the reaction diagram
Pseudomonas putida ML2
-
-
-
-
?
5-methyl-hex-4-ene-1,2-diol + NAD+
5-methyl-hex-1,4-diene-1,2-diol + NADH + H+
show the reaction diagram
Pseudomonas putida, Pseudomonas putida ML2, Pseudomonas putida 8859
-
25% of activity with cis-1,2-dihydrobenzene-1,2-diol
-
-
?
7-methyl-oct-6-ene-1,2-diol + NAD+
7-methyl-oct-1,6-diene-1,2-diol + NADH + H+
show the reaction diagram
Pseudomonas putida, Pseudomonas putida ML2, Pseudomonas putida 8859
-
13% of activity with cis-1,2-dihydrobenzene-1,2-diol
-
-
?
butane-1,2-diol + NAD+
but-1-ene-1,2-diol + NADH
show the reaction diagram
Pseudomonas putida, Pseudomonas putida ML2, Pseudomonas putida 8859
-
29% of activity with cis-1,2-dihydrobenzene-1,2-diol
-
-
?
cis-1,2-cyclohexanediol + NAD+
cyclohex-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
Pseudomonas putida ML2
-
-
-
-
?
cis-1,2-dihydrobenzene-1,2-diol + NAD+
catechol + NADH
show the reaction diagram
-
-
-
?
cis-1,2-dihydrobenzene-1,2-diol + NAD+
catechol + NADH
show the reaction diagram
-
-
-
?
cis-1,2-dihydrobenzene-1,2-diol + NAD+
catechol + NADH
show the reaction diagram
-
-
-
?
cis-1,2-dihydrobenzene-1,2-diol + NAD+
catechol + NADH
show the reaction diagram
-
-
-
?
cis-1,2-dihydrobenzene-1,2-diol + NAD+
catechol + NADH
show the reaction diagram
-
-
-
?
cis-1,2-dihydrobenzene-1,2-diol + NAD+
catechol + NADH
show the reaction diagram
-
-
-
-
?
cis-1,2-dihydrobenzene-1,2-diol + NAD+
catechol + NADH
show the reaction diagram
-
specific for the cis-form of benzene glycol and for NAD+ as a hydrogen acceptor
-
?
cis-1,2-dihydrobenzene-1,2-diol + NAD+
catechol + NADH
show the reaction diagram
-
specific for the cis-form of benzene glycol and for NAD+ as a hydrogen acceptor
-
?
cis-1,2-dihydrobenzene-1,2-diol + NAD+
catechol + NADH
show the reaction diagram
Pseudomonas putida ML2
-
-
-
?
cis-1,2-dihydrobenzene-1,2-diol + NAD+
catechol + NADH
show the reaction diagram
Pseudomonas putida ML2
-
-
-
?
cis-1,2-dihydrobenzene-1,2-diol + NAD+
catechol + NADH
show the reaction diagram
Pseudomonas putida ML2
-
-
-
?
cis-1,2-dihydrobenzene-1,2-diol + NAD+
catechol + NADH
show the reaction diagram
Pseudomonas putida ML2, Pseudomonas putida 8859
-
-
-
-
?
cis-1,2-dihydrobenzene-3-bromo-(R,R)-1,2-diol + NAD+
3-bromocatechol + NADH
show the reaction diagram
Pseudomonas putida, Pseudomonas putida ML2, Pseudomonas putida 8859
-
7% of activity with cis-1,2-dihydrobenzene-1,2-diol
-
-
?
cis-1,2-dihydrobenzene-3-chloro-(R,R)-1,2-diol + NAD+
3-chlorocatechol + NADH
show the reaction diagram
-
22% of activity with cis-1,2-dihydrobenzene-1,2-diol
-
-
?
cis-1,2-dihydrobenzene-3-fluoro-(R,R)-1,2-diol + NAD+
3-fluorocatechol + NADH
show the reaction diagram
-
35% of activity with cis-1,2-dihydrobenzene-1,2-diol
-
-
?
decane-1,2-diol + NAD+
dec-1-ene-1,2-diol + NADH
show the reaction diagram
-
8% of activity with cis-1,2-dihydrobenzene-1,2-diol
-
-
?
glycerol + NAD+
?
show the reaction diagram
Pseudomonas putida, Pseudomonas putida ML2
-
-
-
-
?
naphthalene-cis-1,2-dihydrodiol + NAD+
?
show the reaction diagram
Pseudomonas fluorescens, Pseudomonas fluorescens 26K
-
-
-
-
?
nonane-1,2-diol + NAD+
non-1-ene-1,2-diol + NADH
show the reaction diagram
-
15% of activity with cis-1,2-dihydrobenzene-1,2-diol
-
-
?
propane-1,2-diol + NAD+
prop-1-ene-1,2-diol + NADH
show the reaction diagram
-
36% of activity with cis-1,2-dihydrobenzene-1,2-diol
-
-
?
trimethylbutane-1,2-diol + NAD+
trimethylbut-1-ene-1,2-diol + NADH
show the reaction diagram
-
21% of activity with cis-1,2-dihydrobenzene-1,2-diol
-
-
?
isobutane-1,2-diol + NAD+
isobut-1-ene-1,2-diol + NADH
show the reaction diagram
-
28% of activity with cis-1,2-dihydrobenzene-1,2-diol
-
-
?
additional information
?
-
Pseudomonas fluorescens, Pseudomonas fluorescens 26K
-
NDDH is inactive against cis-1,2-dihydronaphthalene and salicylaldehyde
-
-
-
NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
LITERATURE
(Substrate)
COMMENTARY
(Product)
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
cis-1,2-dihydrobenzene-1,2-diol + NAD+
catechol + NADH
show the reaction diagram
-
-
-
?
cis-1,2-dihydrobenzene-1,2-diol + NAD+
catechol + NADH
show the reaction diagram
-
-
-
?
cis-1,2-dihydrobenzene-1,2-diol + NAD+
catechol + NADH
show the reaction diagram
-
-
-
?
cis-1,2-dihydrobenzene-1,2-diol + NAD+
catechol + NADH
show the reaction diagram
-
-
-
?
cis-1,2-dihydrobenzene-1,2-diol + NAD+
catechol + NADH
show the reaction diagram
-
-
-
?
cis-1,2-dihydrobenzene-1,2-diol + NAD+
catechol + NADH
show the reaction diagram
-
-
-
-
?
cis-1,2-dihydrobenzene-1,2-diol + NAD+
catechol + NADH
show the reaction diagram
Pseudomonas putida ML2
-
-
-
?
cis-1,2-dihydrobenzene-1,2-diol + NAD+
catechol + NADH
show the reaction diagram
Pseudomonas putida ML2
-
-
-
?
cis-1,2-dihydrobenzene-1,2-diol + NAD+
catechol + NADH
show the reaction diagram
Pseudomonas putida ML2
-
-
-
?
cis-1,2-dihydrobenzene-1,2-diol + NAD+
catechol + NADH
show the reaction diagram
Pseudomonas putida ML2, Pseudomonas putida 8859
-
-
-
-
?
naphthalene-cis-1,2-dihydrodiol + NAD+
?
show the reaction diagram
Pseudomonas fluorescens, Pseudomonas fluorescens 26K
-
-
-
-
?
COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
NAD+
-
dependent on
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Fe2+
-
optimum Fe2+ concentration 0.1 mM
additional information
-
no metal ions requirement
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
1,10-phenanthroline
-
-
p-chloromercuribenzoic acid
-
-
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
L-cysteine
-
-
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.01
cis-1,2-dihydrobenzene-1,2-diol
-
cosubstrate NAD+
0.0665
cis-1,2-dihydrobenzene-1,2-diol
-
cosubstrate NAD+
0.12
cis-1,2-dihydrobenzene-1,2-diol
-
30C, pH 8.0
0.286
cis-1,2-dihydrobenzene-1,2-diol
-
cosubstrate NAD+
46
glycerol
-
cosubstrate NAD+
0.0435
NAD+
-
-
0.068
NAD+
-
30C, pH 8.0
0.22
NAD+
-
-
0.57
NAD+
-
-
0.066
naphthalene-cis-1,2-dihydrodiol
-
pH 7.2, 45C
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
0.098
-
crude enzyme extract, pH 7.2, 45C
5.1
-
purified native enzyme, pH 7.2, 45C
19.1
-
cis-1,2-dihydrobenzene-1,2-diol, NAD+
68
-
glycerol, NAD+
153
-
cis-1,2-dihydrobenzene-1,2-diol, NAD+
313
-
cis-1,2-cyclohexanediol, NAD+
513
-
1,2-propanediol, NAD+
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
7.2
-
with NAD+ as cofactor, 83 mM potassium phosphate buffer
7.4
-
with NAD+ as cofactor and Fe2+ ions, 25 mM potassium phosphate buffer
9
-
with NAD+ as cofactor, 100 mM potassium carbonate buffer
pH RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
5 - 9
-
activity range
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
30
-
enzyme assay
30
-
enzyme assay
TEMPERATURE RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
5 - 60
-
activity range
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
Pseudomonas fluorescens 26K
-
-
-
Manually annotated by BRENDA team
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
160000
-
gel filtration
711182
166000
-
PAGE
390589
220000
-
gel filtration
654397
440000
-
ultracentrifugation
390586
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
hexamer
-
6 * 40000, SDS-PAGE
hexamer
Pseudomonas putida ML2, Pseudomonas putida 8859
-
6 * 40000, SDS-PAGE
-
homohexamer
-
6 * 27000, SDS-PAGE
homohexamer
Pseudomonas fluorescens 26K
-
6 * 27000, SDS-PAGE
-
tetramer
-
4 * 110000, SDS-PAGE
tetramer
-
4 * 39000, SDS-PAGE
tetramer
-
4 * 110000, X-ray analysis
tetramer
Pseudomonas putida ML2
-
4 * 110000, X-ray analysis, 4 * 39000, SDS-PAGE
-
Crystallization/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
pH STABILITY
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
7.9
-
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
-
loss of activity by ammonium sulfate precipitation and subsequent dialysis, restored by Fe2+
-
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
enzyme activity is retained during purification and storage in 100 mM Tris-HCl buffer, pH 7.2, containing 5% ethanol
-
less stable at 4C than at -20C, loss of activity at 4C gradually over a few days
-
0-4C or frozen at -22C, concentrated solution, several weeks
-
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
native enzyme from strain 26K by anion exchange and hydrophobic interaction chromatography
-
dye-affinity chromatography and NAD+ agarose chromatography
-
Q-Sepharose, Superdex 200, Mono Q
-
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
-
APPLICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
synthesis
-
preparation of two recombinant strains each containing two enzymatic activities mutually expressed through regulated systems for production of functionalized epoxides in one-pot reactions. The gene coding for styrene monooxygenase from Pseudomonas fluorescens ST and the gene coding for naphthalene dihydrodiol dehydrogenase from Pseudomonas fluorescens N3 are expressed either in Pseudomonas putida PaW340 or in Escherichia coli. The combination of the enzymes allows to obtain the transformation of allylic primary alcohols into alpha,beta-epoxy acids
synthesis
Pseudomonas fluorescens N3
-
preparation of two recombinant strains each containing two enzymatic activities mutually expressed through regulated systems for production of functionalized epoxides in one-pot reactions. The gene coding for styrene monooxygenase from Pseudomonas fluorescens ST and the gene coding for naphthalene dihydrodiol dehydrogenase from Pseudomonas fluorescens N3 are expressed either in Pseudomonas putida PaW340 or in Escherichia coli. The combination of the enzymes allows to obtain the transformation of allylic primary alcohols into alpha,beta-epoxy acids
-
analysis
-
Escherichia coli, which carry genes coding for benzene dioxygenase and benzene dihydrodiol dehydrogenase, can be used to monitor benzene pollution in environmental airsamples collected from an oil refinery. The procedures involving whole-cell bioassays determine the concentration of benzene through benzene dioxygenase activity, which allows for direct correlation of oxygen consumption, and through the benzene dihydrodiol dehydrogenase that causes catechol accumulation and restores NADH necessary for the activity of the first enzyme. The assay is sensitive enough to detect the benzene vapor at a concentration level of 0.01 mM in about 30 min. The assay is applicalble to on-line monitoring of benzene concentration, no particular treatment of environmental samples is required
analysis
Pseudomonas putida MST
-
Escherichia coli, which carry genes coding for benzene dioxygenase and benzene dihydrodiol dehydrogenase, can be used to monitor benzene pollution in environmental airsamples collected from an oil refinery. The procedures involving whole-cell bioassays determine the concentration of benzene through benzene dioxygenase activity, which allows for direct correlation of oxygen consumption, and through the benzene dihydrodiol dehydrogenase that causes catechol accumulation and restores NADH necessary for the activity of the first enzyme. The assay is sensitive enough to detect the benzene vapor at a concentration level of 0.01 mM in about 30 min. The assay is applicalble to on-line monitoring of benzene concentration, no particular treatment of environmental samples is required
-