Information on EC 1.13.11.39 - biphenyl-2,3-diol 1,2-dioxygenase

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The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
1.13.11.39
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RECOMMENDED NAME
GeneOntology No.
biphenyl-2,3-diol 1,2-dioxygenase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
biphenyl-2,3-diol + O2 = 2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoate
show the reaction diagram
also acts on 3-isopropylcatechol, forming 7-methyl-2-hydroxy-6-oxoocta-2,4-dienoate. Not identical with EC1.13.11.2 catechol 2,3-dioxygenase
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
dioxygenation
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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
2-hydroxybiphenyl degradation
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biphenyl degradation
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carbazole degradation
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diphenyl ethers degradation
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Chlorocyclohexane and chlorobenzene degradation
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Dioxin degradation
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Metabolic pathways
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Microbial metabolism in diverse environments
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SYSTEMATIC NAME
IUBMB Comments
biphenyl-2,3-diol:oxygen 1,2-oxidoreductase (decyclizing)
Contains Fe2+ or Mn2+ [3]. This enzyme participates in the degradation pathway of biphenyl and PCB (poly chlorinated biphenyls), and catalyses the first ring cleavage step by incorporating two oxygen atoms into the catechol ring formed by EC 1.3.1.56, cis-2,3-dihydrobiphenyl-2,3-diol dehydrogenase.The enzyme from the bacterium Burkholderia xenovorans LB400 can also process catechol, 3-methylcatechol, and 4-methylcatechol, but less efficiently [1]. The enzyme from the carbazole-degrader Pseudomonas resinovorans strain CA10 also accepts 2'-aminobiphenyl-2,3-diol [5]. The enzyme from Ralstonia sp. SBUG 290 can also accept 1,2-dihydroxydibenzofuran and 1,2-dihydroxynaphthalene [4]. The enzyme is strongly inhibited by the substrate [1].Not identical with EC 1.13.11.2 catechol 2,3-dioxygenase.
CAS REGISTRY NUMBER
COMMENTARY hide
103679-58-9
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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Manually annotated by BRENDA team
LB400
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Manually annotated by BRENDA team
LB400
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Manually annotated by BRENDA team
SMN4
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Manually annotated by BRENDA team
SMN4
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Manually annotated by BRENDA team
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UniProt
Manually annotated by BRENDA team
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Manually annotated by BRENDA team
ATCC 31258
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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
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
activated sludge metagenome, gene bphC_meta
UniProt
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
metabolism
physiological function
additional information
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-dihydroxydibenzofuran + O2
?
show the reaction diagram
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?
1,2-dihydroxynaphthalene + O2
?
show the reaction diagram
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-
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?
2',3',5'-trichloro-2,3-dihydroxybiphenyl + O2
2-hydroxy-6-oxo-6-(2',3',5'-trichlorophenyl)-hexa-2,4-dienoate + H2O
show the reaction diagram
2',3'-dichloro-2,3-dihydroxybiphenyl + O2
2-hydroxy-6-oxo-6-(2',3'-dichlorophenyl)-hexa-2,4-dienoate + H2O
show the reaction diagram
2',4'-dichloro-2,3-dihydroxybiphenyl + O2
2-hydroxy-6-oxo-6-(2',4'-dichlorophenyl)-hexa-2,4-dienoate + H2O
show the reaction diagram
2'-aminobiphenyl-2,3-diol + O2
(2E,4E)-6-(2-aminophenyl)-2-hydroxy-6-oxohexa-2,4-dienoate + H+
show the reaction diagram
2'-aminobiphenyl-2,3-diol + O2
?
show the reaction diagram
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?
2'-chloro-2,3-dihydroxybiphenyl + O2
2-hydroxy-6-oxo-6-(2'-chlorophenyl)-hexa-2,4-dienoate + H2O
show the reaction diagram
2,2',3,3'-tetrachlorobiphenyl + O2
?
show the reaction diagram
-
-
-
-
?
2,2',3-trihydroxybiphenyl + O2
?
show the reaction diagram
-
-
-
-
?
2,2'-dibromobiphenyl + O2
?
show the reaction diagram
2,2'-dichlorobiphenyl + O2
?
show the reaction diagram
-
-
-
-
?
2,2'-dichlorobiphenyl + O2
cis-5,6-dihydro-5,6-dihydroxy-2,2'-dichlorobiphenyl
show the reaction diagram
-
-
-
-
?
2,2'-difluorobiphenyl + O2
?
show the reaction diagram
2,2'-dihydroxybiphenyl + O2
6-(2-hydroxyphenyl)-6-oxohexa-2,4-dienoate
show the reaction diagram
2,2'-dinitrobiphenyl + O2
?
show the reaction diagram
2,3-dihydroxy-3'-chlorobiphenyl + O2
2-hydroxy-6-oxo-6-(3'-chlorophenyl)-hexa-2,4-dienoate + H2O
show the reaction diagram
2,3-dihydroxybiphenyl + O2
2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoate
show the reaction diagram
2,3-dihydroxybiphenyl + O2
2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoate + H2O
show the reaction diagram
3',4',5'-trichloro-2,3-dihydroxybiphenyl + O2
2-hydroxy-6-oxo-6-(3',4',5'-trichlorophenyl)-hexa-2,4-dienoate + H2O
show the reaction diagram
3',4'-dichloro-2,3-dihydroxybiphenyl + O2
2-hydroxy-6-oxo-6-(3',4'-dichlorophenyl)-hexa-2,4-dienoate + H2O
show the reaction diagram
3',5'-dichloro-2,3-dihydroxybiphenyl + O2
2-hydroxy-6-oxo-6-(3',5'-dichlorophenyl)-hexa-2,4-dienoate + H2O
show the reaction diagram
3'-chloro-2,3-dihydroxybiphenyl + O2
2-hydroxy-6-oxo-6-(3'-chlorophenyl)-hexa-2,4-dienoate + H2O
show the reaction diagram
3,3'-dichlorobiphenyl + O2
?
show the reaction diagram
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?
3,5-dichlorocatechol + O2
3,5-dichloro-2-hydroxy-6-oxohexa-2,4-dienoate
show the reaction diagram
3-chlorocatechol + O2
3-chloro-2-hydroxymuconic semialdehyde + H2O
show the reaction diagram
3-chlorocatechol + O2
?
show the reaction diagram
3-ethylcatechol + O2
2-hydroxy-7-methyl-6-oxoocta-2,4-dienoate
show the reaction diagram
3-formylcatechol + O2
?
show the reaction diagram
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?
3-isoporopylcatechol + O2
2-hydroxy-7-methyl-6-oxo-octa-2,4-dienoate + ?
show the reaction diagram
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relative activity 179%
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?
3-isopropylcatechol + O2
2-hydroxy-7-methyl-6-oxo-octa-2,4-dienoate + ?
show the reaction diagram
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?
3-methoxycatechol + O2
2-hydroxy-3-methoxy-6-oxohexa-2,4-dienoate
show the reaction diagram
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relative activity 13%
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?
3-methylcatechol + O2
2-hydroxy-6-oxohepta-2,4-dienoate
show the reaction diagram
3-methylcatechol + O2
?
show the reaction diagram
4'-chloro-2,3-dihydroxybiphenyl + O2
2-hydroxy-6-oxo-6-(4'-chlorophenyl)-hexa-2,4-dienoate + H2O
show the reaction diagram
4,4'-dichlorobiphenyl + O2
?
show the reaction diagram
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?
4-chloro-2,3-dihydroxybiphenyl + O2
3-chloro-2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoate
show the reaction diagram
4-chlorobiphenyl + O2
?
show the reaction diagram
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?
4-chlorocatechol + O2
4-chloro-2-hydroxy-6-oxohexa-2,4-dienoate
show the reaction diagram
4-chlorocatechol + O2
?
show the reaction diagram
4-methylcatechol + O2
2-hydroxy-4-methyl-6-oxohexa-2,4-dienoate
show the reaction diagram
4-methylcatechol + O2
?
show the reaction diagram
biphenyl + O2
?
show the reaction diagram
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?
biphenyl-2,3-diol + O2
2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoate
show the reaction diagram
biphenyl-2,3-diol + O2
2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoate + H2O
show the reaction diagram
catechol + O2
2-hydroxymuconate semialdehyde
show the reaction diagram
catechol + O2
2-hydroxymuconic semialdehyde
show the reaction diagram
catechol + O2
?
show the reaction diagram
cis-5,6-dihydro-5,6-dihydroxy-2,2'-dichlorobiphenyl + O2
?
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
biphenyl-2,3-diol + O2
2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoate
show the reaction diagram
biphenyl-2,3-diol + O2
2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoate + H2O
show the reaction diagram
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Fe
0.8 mol iron per mol subunit of BphC1; 1.0 mol iron per mol subunit of BphC1
Fe3+
1 mM, activates
Iron
-
ferrous enzyme
Manganese
enzyme contains 4.0-4.8 manganese atoms per enzyme molecule, depending on the batch
additional information
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
1,10-phenanthroline
2,3-Dihydroxybiphenyl
2-Hydroxypyridine N-oxide
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0.2 mM
3,4-dihydroxybiphenyl
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strain CB406, inactivation in presence of O2
3-chlorocatechol
3-ethylcatechol
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reversible substrate inhibition
3-methylcatechol
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4-Chlorocatechol
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4-methylcatechol
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8-hydroxyquinoline
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5 mM 30 min
acetone
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competitive inhibition
alpha,alpha'-dipyridyl
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inhibits catalysis, but protects the Fe2+ from oxidative inactivation
Ba2+
1 mM, moderate inhibition
diethyldithiocarbamic acid
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5 mM 30 min
Hg2+
1 mM, complete inhibition
iodoacetic acid
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5 mM 30 min
isopropylalcohol
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L-ascorbic acid
completely inhibits at concentrations over 25 mM
N-ethylmaleimide
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5 mM 30 min
Ni2+
1 mM, strong inhibition
o-phenanthroline
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tert-butanol
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Zn2+
1 mM, complete inhibition with substrate biphenyl-2,3-diol, not with catechols
additional information
-
do not cleave 3,4-dihydroxybiphenyl, but is not inactivated
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.014
2'-aminobiphenyl-2,3-diol
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pH 7.5, 25C
0.001 - 0.019
2'-chloro-2,3-dihydroxybiphenyl
0.0026
2,2'-dichlorobiphenyl
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-
0.000095 - 0.74
2,3-Dihydroxybiphenyl
0.00045 - 0.01
3'-chloro-2,3-dihydroxybiphenyl
0.0033
3,3'-dichlorobiphenyl
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-
0.007 - 0.03
3,5-dichlorocatechol
0.025 - 2.1
3-chlorocatechol
0.0108
3-formylcatechol
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in 50 mM Hepes (pH 7.5) at 25C
0.001 - 14.6
3-methylcatechol
0.0015 - 0.012
4'-chloro-2,3-dihydroxybiphenyl
0.025 - 0.0496
4-Chlorocatechol
0.0273 - 93
4-methylcatechol
0.0062
biphenyl
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-
0.00046 - 0.087
biphenyl-2,3-diol
0.0062 - 2.4
catechol
0.028 - 1.28
O2
additional information
additional information
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.25 - 7.5
2'-chloro-2,3-dihydroxybiphenyl
4.8 - 84.1
2,3-Dihydroxybiphenyl
4 - 12
3'-chloro-2,3-dihydroxybiphenyl
4 - 15
3-chlorocatechol
0.8
3-formylcatechol
-
in 50 mM Hepes (pH 7.5) at 25C
3 - 44
3-methylcatechol
4.5 - 18.8
4'-chloro-2,3-dihydroxybiphenyl
1
4-Chlorocatechol
pH 8.0, 20C
0.064 - 43.2
4-methylcatechol
8.78 - 165
biphenyl-2,3-diol
0.016 - 52.56
catechol
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
250
2'-aminobiphenyl-2,3-diol
-
pH 7.5, 25C
4450
2,3-Dihydroxybiphenyl
pH 8.0, 20C
89.8 - 10300
3-methylcatechol
20
4-Chlorocatechol
pH 8.0, 20C
2 - 1582
4-methylcatechol
224.6 - 40530
biphenyl-2,3-diol
24 - 8477
catechol
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
3
2,3-Dihydroxybiphenyl
-
reversible substrate inhibition
0.22
3-chlorocatechol
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-
11
3-ethylcatechol
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13
acetone
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35
ethanol
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10.5
isopropylalcohol
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5.2 - 9.9
tert-butanol
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.17
-
using 4-methylcatechol as substrate
0.33
-
using 1,2-dihydroxynaphthalene as substrate; using catechol as substrate
0.52
-
cell extract
1.88
-
using 1,2-dihydroxydibenzofuran as substrate
2.19
-
using 3-isopropylcatechol as substrate
3.1
-
BphC1
3.75
-
using 3-methylcatechol as substrate
4.79
-
using 2,3-dihydroxybiphenyl as substrate
6.88
-
after 13.2fold purification
10.74
-
pH 8.0, 30C, immobilized enzyme, substrate biphenyl-2,3-diol
57.3
-
strain OU83
118.3
with 2,3-dihydroxybiphenyl as substrate
additional information
-
no substrate specificity for 3,4-dihydroxybiphenyl, 2,3-dihydroxydibenzofuran, 3-chlorocatechol, 4-chlorocatechol, and pyrogallol
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
5 - 10
6 - 10
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activity range of immobilized enzyme
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
20
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assay at
20 - 25
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for meta-cleavage of 1,2-dihydroxydibenzofuran
45
-
immobilized enzyme
50
recombinant enzyme
TEMPERATURE RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
10 - 60
activity range, profile overview; activity range, profile overview; activity range, profile overview
15 - 55
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activity range of immobilized enzyme
20 - 80
activity range
20 - 70
20C: about 75% of maximal activity, 70C: about 85% of maximal activity
pI VALUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
4.5
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isoelectric focusing
PDB
SCOP
CATH
ORGANISM
UNIPROT
Paraburkholderia xenovorans (strain LB400)
Paraburkholderia xenovorans (strain LB400)
Paraburkholderia xenovorans (strain LB400)
Paraburkholderia xenovorans (strain LB400)
Paraburkholderia xenovorans (strain LB400)
Paraburkholderia xenovorans (strain LB400)