Information on EC 1.3.1.29 - cis-1,2-dihydro-1,2-dihydroxynaphthalene dehydrogenase

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The expected taxonomic range for this enzyme is: Bacteria, Eukaryota

EC NUMBER
COMMENTARY hide
1.3.1.29
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RECOMMENDED NAME
GeneOntology No.
cis-1,2-dihydro-1,2-dihydroxynaphthalene dehydrogenase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
(1R,2S)-1,2-dihydronaphthalene-1,2-diol + NAD+ = naphthalene-1,2-diol + NADH + H+
show the reaction diagram
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
oxidation
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redox reaction
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reduction
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
naphthalene degradation (aerobic)
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Polycyclic aromatic hydrocarbon degradation
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Naphthalene degradation
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Metabolic pathways
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Microbial metabolism in diverse environments
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SYSTEMATIC NAME
IUBMB Comments
cis-1,2-dihydronaphthalene-1,2-diol:NAD+ 1,2-oxidoreductase
Also acts, at half the rate, on cis-anthracene dihydrodiol and cis-phenanthrene dihydrodiol.
CAS REGISTRY NUMBER
COMMENTARY hide
53986-49-5
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
strain C125
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Manually annotated by BRENDA team
strain C125
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Manually annotated by BRENDA team
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-
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Manually annotated by BRENDA team
strain CHY-1
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Manually annotated by BRENDA team
strain N3
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Manually annotated by BRENDA team
strain N3
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Manually annotated by BRENDA team
strain 8859
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Manually annotated by BRENDA team
strain G7
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Manually annotated by BRENDA team
strain NCIB 9816
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Manually annotated by BRENDA team
strain NCIMB12038
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Manually annotated by BRENDA team
strain NCIMB12038
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Manually annotated by BRENDA team
strain ES11
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Manually annotated by BRENDA team
strain ES11
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-
Manually annotated by BRENDA team
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(1R,2S)-cis-1,2-dihydronaphthalene-1,2-diol + NAD+
naphthalene-1,2-diol + NADH
show the reaction diagram
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best substrate, stereospecific for the (1R,2S)-enantiomer, no activity with the (1S,2R)-enantiomer
-
-
?
(1S,2R)-1,2-dihydroxy-3-methylcyclohexa-3,5-diene + NAD+
?
show the reaction diagram
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-
-
-
?
(1S,2R)-1,2-dihydroxy-3-phenylcyclohexa-3,5-diene + NAD+
?
show the reaction diagram
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-
-
-
?
(1S,2S)-1,2-dihydroxy-3-bromocyclohexa-3,5-diene + NAD+
?
show the reaction diagram
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stereospecific for the (1S,2S)-enantiomer, no activity with the (1R,2R)-enantiomer
-
-
?
(1S,2S)-1,2-dihydroxy-3-chlorocyclohexa-3,5-diene + NAD+
?
show the reaction diagram
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stereospecific for the (1S,2S)-enantiomer, no activity with the (1R,2R)-enantiomer
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-
?
(1S,2S)-1,2-dihydroxy-3-fluorocyclohexa-3,5-diene + NAD+
?
show the reaction diagram
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stereospecific for the (1S,2S)-enantiomer, no activity with the (1R,2R)-enantiomer
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-
?
(1S,2S)-1,2-dihydroxy-3-iodocyclohexa-3,5-diene + NAD+
?
show the reaction diagram
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stereospecific for the (1S,2S)-enantiomer, no activity with the (1R,2R)-enantiomer
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-
?
1,2,5,6,7,8-hexahydro-cis-1,2-naphthalene diol + NAD+
5,6,7,8-tetrahydro-1,2-naphthalene diol + NADH + H+
show the reaction diagram
2,3-dihydroxy-2,3-dihydrobiphenyl + NAD+
2,3-dihydroxybiphenyl + NADH + H+
show the reaction diagram
3,4-dihydro-3,4-dihydroxy-2,2',5,5'-tetrachlorobiphenyl + NAD+
3,4-dihydroxy-2,2',5,5'-tetrachlorobiphenyl + NADH
show the reaction diagram
anthracene 1,2-dihydrodiol + NAD+
anthracene 1,2-diol + NADH + H+
show the reaction diagram
benzo(a)anthracene 1,2-dihydrodiol + NAD+
benzo(a)anthracene 1,2-diol + NADH + H+
show the reaction diagram
benzo(a)pyrene-9,10-dihydrodiol + NAD+
9,10-dihydroxy-benzo(a)pyrene + NADH + H+
show the reaction diagram
chrysene 3,4-dihydrodiol + NAD+
chrysene 3,4-diol + NADH + H+
show the reaction diagram
cis-(1R,2S)-dihydroxy-1,2-dihydronaphthalene + NAD+
1,2-dihydroxynaphthalene + NADH
show the reaction diagram
cis-1,2-dihydrobenzene-1,2-diol + NAD+
benzene-1,2-diol + NADH
show the reaction diagram
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?
cis-1,2-dihydronaphthalene-1,2-diol + NAD+
naphthalene-1,2-diol + NADH
show the reaction diagram
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-
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?
cis-2,3-dihydro-2,3-dihydroxybiphenyl + NAD+
cis-2,3-dihydroxybiphenyl + NADH
show the reaction diagram
cis-anthracene dihydrodiol + NAD+
1,2-dihydroxyanthracene + NADH
show the reaction diagram
cis-benzene dihydrodiol + NAD+
1,2-dihydroxybenzene + NADH
show the reaction diagram
cis-biphenyl dihydrodiol + NAD+
3-phenyl-1,2-dihydroxybenzene + NADH
show the reaction diagram
cis-ethylbenzene dihydrodiol + NAD+
3-ethyl-1,2-dihydroxybenzene + NADH
show the reaction diagram
cis-phenanthrene dihydrodiol + NAD+
3,4-dihydroxyphenanthrene + NADH
show the reaction diagram
cis-toluene dihydrodiol + NAD+
3-methyl-1,2-dihydroxybenzene + NADH
show the reaction diagram
fluoranthene 2,3-dihydrodiol + NAD+
2,3-dihydroxyfluoranthene + NADH + H+
show the reaction diagram
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?
naphthalene-1,2-dihydrodiol + NAD+
naphthalene-1,2-diol + NADH + H+
show the reaction diagram
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?
phenanthrene 3,4-dihydrodiol + NAD+
phenanthrene 3,4-diol + NADH + H+
show the reaction diagram
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?
pyrene 4,5-dihydrodiol + NAD+
4,5-dihydroxypyrene + NADH + H+
show the reaction diagram
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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-dihydronaphthalene-1,2-diol + NAD+
naphthalene-1,2-diol + NADH
show the reaction diagram
-
-
-
-
?
additional information
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
NADP+
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activity 25fold lower than with NAD+
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
2,2'-dipyridyl
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16.7 mM, 55% inhibition
3,4-Dihydroxyphenanthrene
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8-hydroxyquinoline
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16.7 mM, 25% inhibition
EDTA
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16.7 mM, 17% inhibition
p-chloromercuribenzoate
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16.7 mM, 87% inhibition
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.062
3,4-dihydro-3,4-dihydroxy-2,2',5,5'-tetrachlorobiphenyl
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strain G7
0.002
anthracene 1,2-dihydrodiol
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0.0071
benzo(a)anthracene 1,2-dihydrodiol
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0.0035 - 0.0036
biphenyl 2,3-dihydrodiol
0.0022 - 0.0057
chrysene 3,4-dihydrodiol
0.11
cis-2,3-dihydro-2,3-dihydroxybiphenyl
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strain G7
0.05
cis-benzene dihydrodiol
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strain biotype A grown on benzene
0.011 - 0.8
cis-Naphthalene dihydrodiol
0.024
cis-Toluene dihydrodiol
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strain biotype A grown on toluene
0.029 - 1.04
NAD+
0.00141
naphthalene 1,2-dihydrodiol
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0.00185
phenanthrene 3,4-dihydrodiol
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.1
3,4-dihydro-3,4-dihydroxy-2,2',5,5'-tetrachlorobiphenyl
Pseudomonas putida
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strain G7
21.6
anthracene 1,2-dihydrodiol
Novosphingobium aromaticivorans
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9.1
benzo(a)anthracene 1,2-dihydrodiol
Novosphingobium aromaticivorans
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7.9
benzo(a)pyrene dihydrodiol
Novosphingobium aromaticivorans
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24.6 - 321
biphenyl 2,3-dihydrodiol
20.3 - 218
chrysene 3,4-dihydrodiol
51.7
cis-2,3-dihydro-2,3-dihydroxybiphenyl
Pseudomonas putida
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strain G7
149
cis-Naphthalene dihydrodiol
Pseudomonas putida
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strain G7
5.25
fluoranthene 2,3-dihydrodiol
Novosphingobium aromaticivorans
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28.2
naphthalene 1,2-dihydrodiol
Novosphingobium aromaticivorans
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16.7
phenanthrene 3,4-dihydrodiol
Novosphingobium aromaticivorans
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6.35
pyrene 4,5-dihydrodiol
Novosphingobium aromaticivorans
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.0041
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recombinant enzyme expressed in Escherichia coli
0.007
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activity in extracts of cells grown on succinate, substrate cis-benzene diol
0.008
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activity in extracts of cells grown on succinate, substrate 1,2,5,6,7,8-hexahydro-cis-1,2-naphthalene diol
0.012
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activity in extracts of cells grown on succinate, substrate cis-toluene diol
0.015 - 0.03
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recombinant enzyme expressed in Escherichia coli
0.03
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recombinant enzyme expressed in Escherichia coli, induction with salicylate
0.032
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enzyme activity in crude extracts of strain PL6 grown on medium containing arginine and salicylate
0.036
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activity in extracts of cells grown on tetralin, substrate cis-benzene diol
0.041
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activity in extracts of cells grown on o-xylene, substrate cis-benzene diol
0.067
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activity in extracts of cells grown on tetralin, substrate 1,2,5,6,7,8-hexahydro-cis-1,2-naphthalene diol
0.084
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activity in extracts of cells grown on o-xylene, substrate 1,2,5,6,7,8-hexahydro-cis-1,2-naphthalene diol
0.09 - 0.182
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recombinant enzyme expressed in Pseudomonas putida
0.096
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activity in extracts of cells grown on o-xylene, substrate cis-toluene diol
0.103
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activity in extracts of cells grown on tetralin, substrate cis-toluene diol
0.14
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enzyme activity in crude extracts of strain C84-15
0.19
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activity in crude extracts
0.205
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enzyme activity in crude extracts of strain NP
0.21
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enzyme activity in crude extracts of strain NCIB 9816
0.25
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activity in crude extracts of strain NP
0.39
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recombinant enzyme expressed in Pseudomonas putida strain AC10
0.42
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activity in crude extracts of strain NCIB
0.62
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activity in crude extracts of strain biotype A grown on benzene
0.94
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activity in crude extracts of strain biotype A grown on toluene
12
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purified enzyme, substrate (1R,2S)-cis-1,2-dihydronaphthalene-1,2-diol
16
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purified enzyme, substrate (1S,2R)-1,2-dihydroxy-3-phenylcyclohexa-3,5-diene
19
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purified enzyme, substrate (1S,2S)-1,2-dihydroxy-3-chlorocyclohexa-3,5-diene
20
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purified enzyme, substrate (1S,2S)-1,2-dihydroxy-3-fluorocyclohexa-3,5-diene
20.6
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purified enzyme, substrate (1S,2S)-1,2-dihydroxy-3-bromocyclohexa-3,5-diene
21.4
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purified enzyme, substrate (1S,2S)-1,2-dihydroxy-3-iodocyclohexa-3,5-diene
22
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purified enzyme, substrate (1S,2R)-1,2-dihydroxy-3-methylcyclohexa-3,5-diene
26
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purified enzyme, substrate cis-1,2-dihydrobenzene-1,2-diol
additional information
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
8
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assay at
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
30
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assay at
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
92000
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gel filtration
102000
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gel filtration
103000
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gel filtration
112000
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strain NCIB 9816, gel filtration
155000 - 160000
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biotype A, depending on growth medium, gel filtration
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
tetramer
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
2-mercaptoethanol stabilizes
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STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
4°C, 11 days, little loss of activity
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Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
by Co2+-loaded immobilized metal affinity chromatography
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to homogeneity by ion exchange chromatography and gel filtration
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expressed in Escherichia coli strain JM109
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expression in Escherichia coli
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expression in Escherichia coli and Pseudomonas putida
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into pET15b and overexpressed as His-tagged protein in Escherichia coli BL21(DE3)
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