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Information on EC 1.14.12.18 - biphenyl 2,3-dioxygenase
for references in articles please use BRENDA:EC1.14.12.18
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EC Tree 1 Oxidoreductases
1.14 Acting on paired donors, with incorporation or reduction of molecular oxygen
1.14.12 With NADH or NADPH as one donor, and incorporation of two atoms of oxygen into the other donor
1.14.12.18 biphenyl 2,3-dioxygenase
IUBMB Comments
Requires Fe2+. The enzyme from Burkholderia fungorum LB400 (previously Pseudomonas sp.) is part of a multicomponent system composed of an NADH:ferredoxin oxidoreductase (FAD cofactor), a [2Fe-2S] Rieske-type ferredoxin, and a terminal oxygenase that contains a [2Fe-2S] Rieske-type iron-sulfur cluster and a catalytic mononuclear nonheme iron centre. Chlorine-substituted biphenyls can also act as substrates. Similar to the three-component enzyme systems EC 1.14.12.3 (benzene 1,2-dioxygenase) and EC 1.14.12.11 (toluene dioxygenase).
The enzyme appears in viruses and cellular organisms
- 1.14.12.18
- biphenyls
-
polychlorinated
- pseudoalcaligenes
- xenovorans
-
chlorobiphenyls
-
dihydrodiols
- comamonas
-
rieske-type
- testosteroni
-
pcb-degrading
-
bpdos
-
pcb-contaminated
- yanoikuyae
-
2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoic
- 2,3-dihydroxybiphenyls
-
biphenyl-degrading
-
cis-dihydrodiols
- globerulus
-
ring-hydroxylating
- pnomenusa
-
2,2\'-dichlorobiphenyl
-
pandoraea
-
polychlorobiphenyls
-
biphenyl-utilizing
- synthesis
- beijerinckia
-
chlorobenzoates
-
biphenyl-induced
-
2,2\',5,5\'-tetrachlorobiphenyl
Reaction Schemes
showSynonyms
biphenyl dioxygenase, bpha1, bph dox, biphenyl 2,3-dioxygenase, bphabc, bphae, biphenyl-2,3-dioxygenase, bphabcd, bpdolb400, 2,3-biphenyl dioxygenase, more
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
2,3-biphenyl dioxygenase
BDO
biphenyl 2, 3-dioxygenase
Biphenyl 2,3-dioxygenase
biphenyl dioxygenase
BPDO
BPDOB356
BPDOLB400
BPH
BPH dox
BphA
BphA1
BphABC
BphABCD
BphAE
BPO
-
-
-
-
ThebphA1fA2f
BDO
-
-
-
-
Biphenyl 2,3-dioxygenase
-
-
-
-
biphenyl dioxygenase
-
-
-
-
biphenyl dioxygenase
-
-
biphenyl dioxygenase
-
the enzyme is composed of BphA1, BphA2 [large (alpha) and small (beta) subunits of an iron-sulfur protein, respectively], BphA3 (ferredoxin), and BphA4 (ferredoxin reductase)
biphenyl dioxygenase
Pseudomonas oleovorans KF707
-
the enzyme is composed of BphA1, BphA2 [large (alpha) and small (beta) subunits of an iron-sulfur protein, respectively], BphA3 (ferredoxin), and BphA4 (ferredoxin reductase)
-
biphenyl dioxygenase
A5YWJ0, A5YWJ1, A5YWJ2, A5YWJ3, A5YWJ4, A5YWJ5, A5YWJ6, A5YWJ7, A5YWJ8, A5YWJ9, A5YWK0, A5YWK1, A5YWK2, A5YWK3, A5YWK4, A5YWK5, A5YWK6
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BPDO
-
-
-
-
BPDO
A5YWJ0, A5YWJ1, A5YWJ2, A5YWJ3, A5YWJ4, A5YWJ5, A5YWJ6, A5YWJ7, A5YWJ8, A5YWJ9, A5YWK0, A5YWK1, A5YWK2, A5YWK3, A5YWK4, A5YWK5, A5YWK6
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BPH dox
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-
-
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
biphenyl + NADH + H+ + O2 = (1S,2R)-3-phenylcyclohexa-3,5-diene-1,2-diol + NAD+
with chlorinated biphenyls the product is 2,3-dihydroxybiphenyl and HCl
-
biphenyl + NADH + H+ + O2 = (1S,2R)-3-phenylcyclohexa-3,5-diene-1,2-diol + NAD+
with chlorinated biphenyls the product is 2,3-dihydroxybiphenyl and HCl
-
-
biphenyl + NADH + H+ + O2 = (1S,2R)-3-phenylcyclohexa-3,5-diene-1,2-diol + NAD+
-
-
-
-
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
oxidation
-
-
-
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redox reaction
reduction
-
-
-
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redox reaction
-
-
-
-
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PATHWAY SOURCE
PATHWAYS
MetaCyc
biphenyl degradation, diphenyl ethers degradation
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SYSTEMATIC NAME
IUBMB Comments
biphenyl,NADH:oxygen oxidoreductase (2,3-hydroxylating)
Requires Fe2+. The enzyme from Burkholderia fungorum LB400 (previously Pseudomonas sp.) is part of a multicomponent system composed of an NADH:ferredoxin oxidoreductase (FAD cofactor), a [2Fe-2S] Rieske-type ferredoxin, and a terminal oxygenase that contains a [2Fe-2S] Rieske-type iron-sulfur cluster and a catalytic mononuclear nonheme iron centre. Chlorine-substituted biphenyls can also act as substrates. Similar to the three-component enzyme systems EC 1.14.12.3 (benzene 1,2-dioxygenase) and EC 1.14.12.11 (toluene dioxygenase).
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CAS REGISTRY NUMBER
COMMENTARY
103289-55-0
-
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
LITERATURE
COMMENTARY
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
(3R,4R)-cis-isoflavan-4-ol + NADH + H+ + O2
(3R,4R)-3-(7-oxabicyclo[4.1.0]hepta-1,3,5-trien-2-yl)-3,4-dihydro-2H-chromen-4-ol + NAD+
(3R,4S)-trans-isoflavan-4-ol + NADH + H+ + O2
(3R,4S)-3-(7-oxabicyclo[4.1.0]hepta-1,3,5-trien-2-yl)-3,4-dihydro-2H-chromen-4-ol + NAD+
(3S,4R)-trans-isoflavan-4-ol + NADH + H+ + O2
(3S,4R)-3-(7-oxabicyclo[4.1.0]hepta-1,3,5-trien-2-yl)-3,4-dihydro-2H-chromen-4-ol + NAD+
(3S,4S)-cis-isoflavan-4-ol + NADH + H+ + O2
(3S,4S)-3-(7-oxabicyclo[4.1.0]hepta-1,3,5-trien-2-yl)-3,4-dihydro-2H-chromen-4-ol + NAD+
-
Substrates: -
Products: -
Products: -
?
2,2',3,3'-tetrachlorobiphenyl + NADH + H+ + O2
5,6-dihydro-5,6-dihydroxy-2,2',3,3'-tetrachlorobiphenyl + 4,5-dihydro-4,5-dihydroxy-2,2',3,3'-tetrachlorobiphenyl + NAD+
-
Substrates: -
Products: -
Products: -
?
2,2',5,5'-tetrachlorobiphenyl + NADH + H+ + O2
3,4-dihydro-3,4-dihydroxy-2,2',5,5'-tetrachlorobiphenyl + NAD+
-
Substrates: -
Products: -
Products: -
?
2,2'-dichlorobiphenyl + NADH + H+ + O2
2,3-dihydroxy-2'-chlorobiphenyl + 3,4-dihydro-3,4-dihydroxy-2,2'-dichlorobiphenyl + NAD+ + HCl
2,2'-dichlorobiphenyl + NADH + H+ + O2
2,3-dihydroxy-2'-chlorobiphenyl + cis-3,4-dihydro-3,4-dihydroxy-2,2'-dichlorobiphenyl + NAD+ + HCl
-
Substrates: -
Products: -
Products: -
?
2,2'-dichlorobiphenyl + NADH + H+ + O2
2,3-dihydroxy-2'-chlorobiphenyl + NAD+ + HCl
-
Substrates: poor substrate
Products: -
Products: -
?
2,2'-dichlorobiphenyl + NADH + O2
2,3-dihydroxy-2'-chlorobiphenyl + 3,4-dihydro-3,4-dihydroxy-2,2'-dichlorobiphenyl + NAD+
2,2'-dichlorobiphenyl + NADH + O2
5,6-dihydroxy-1-phenylcyclohexa-1,3-diene + 2,3-dihydroxy-2'-chlorobiphenyl + NAD+ + HCl
2,2'-difluorobiphenyl + NADH + O2
2,3-dihydroxy-2'-fluorobiphenyl + 5,6-dihydroxy-2,2'-difluorobiphenyl + NAD+ + HF
2,3'-dichlorobiphenyl + NADH + H+ + O2
3-chloro-5-(2-chlorophenyl)cyclohexa-3,5-diene-1,2-diol + 4-chloro-3-(3-chlorophenyl)cyclohexa-3,5-diene-1,2-diol + 5-chloro-3-(2-chlorophenyl)cyclohexa-3,5-diene-1,2-diol
2,3'-dichlorobiphenyl + NADH + O2
5,6-dihydroxy-1-phenylcyclohexa-1,3-diene + 2,3-dihydroxy-3'-chlorobiphenyl + 5',6'-dihydroxy-1'-phenylcyclohexa-1',3'-diene + NAD+ + HCl
-
Substrates: -
Products: -
Products: -
?
2,3,2',3'-tetrachlorobiphenyl + NADH + H+ + O2
4,5-dihydro-4,5-dihydroxy-2,3,2',3'-tetrachlorobiphenyl + NAD+
-
Substrates: oxygenated onto meta-para carbons 4 and 5
Products: -
Products: -
?
2,3,2',3'-tetrachlorobiphenyl + NADH + H+ + O2
cis-4,5-dihydro-4,5-dihydroxy-2,3,2',3'-tetrachlorobiphenyl + NAD+
-
Substrates: -
Products: -
Products: -
?
2,4',5-trichlorobiphenyl + NADH + H+ + O2
3,4-dihydro-3,4-dihydroxy-2,5,4'-trichlorobiphenyl + 2',3'-dihydro-2',3'-dihydroxy-2,5,4'-trichlorobiphenyl + NAD+
-
Substrates: -
Products: -
Products: -
?
2,4,2',4'-tetrachlorobiphenyl + NADH + H+ + O2
2,3-dihydroxy-2',4,4'-trichlorobiphenyl + NAD+ + HCl
-
Substrates: oxygenated principally onto vicinal ortho-meta carbons 2 and 3
Products: -
Products: -
?
2,4,4'-trichlorobiphenyl + NADH + H+ + O2
2,3-dihydro-2,3-dihydroxy-2',4,4'-trichlorobiphenyl + NAD+
2,5,2',5'-tetrachlorobiphenyl + NADH + O2
cis-3,4-dihydroxy-2,5-dichloro-1-[2',5'-dichlorophenyl]-cyclohexa-1,5-diene + 3,4-dihydroxy-1-phenylcyclohexa-1,5-diene + NAD+ + HCl
2,5,2'-trichlorobiphenyl + NADH + O2
cis-3,4-dihydroxy-2,5-dichloro-1-[2'-chlorophenyl]-cyclohexa-1,5-diene + 2',3'-dihydroxy-2,5-dichlorobiphenyl + NAD+ + HCl
-
Substrates: -
Products: -
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?
2,5,3'-trichlorobiphenyl + NADH + O2
3,4-dihydroxy-1-phenylcyclohexa-1,5-diene + 5',6'-dihydroxy-1'-phenylcyclohexa-1',3'-diene + 2,3-catechol + NAD+ + HCl
-
Substrates: -
Products: -
Products: -
?
2,5-dichlorobiphenyl + NADH + O2
cis-2',3'-dihydroxy-1'-(2,5-dichlorophenyl)-cyclohexa-4',6'-diene + 3,4-dihydroxy-1-phenylcyclohexa-1,5-diene + NAD+ + HCl
2,6',4'-trichlorobiphenyl + NADH + O2
?
-
Substrates: -
Products: -
Products: -
?
2,6-dichlorobiphenyl + NADH + H+ + O2
2,6-dichloro-2',3'-dihydro-2',3'-dihydroxybiphenyl + ?
2,6-dichlorobiphenyl + NADH + H+ + O2
?
-
Substrates: poor substrate
Products: -
Products: -
?
2-chlorobiphenyl + NADH + O2
cis-2',3'-dihydroxy-1'-(2-chlorophenyl)-cyclohexa-4',6'-diene + catechol + NAD+
2-hydroxy-3-chlorobiphenyl + NADH + H+ + O2
5-(3-chloro-2-hydroxyphenyl)-6-hydroxy-3-cyclohexen-1-one + NAD+
2-hydroxy-5-chlorobiphenyl + NADH + H+ + O2
cis-2,3-dihydro-2,3-dihydroxy-2'-hydroxy-5'-chlorobiphenyl + 5-(5-chloro-2-hydroxyphenyl)-6-hydroxy-3-cyclohexene-1-one + 2,2'-dihydroxy-5-chlorobiphenyl + 2,3'-dihydroxy-5-chlorobiphenyl + NAD+
3,3'-dichlorobiphenyl + NADH + H+ + O2
5,6-dihydroxy-1-phenylcyclohexa-1,3-diene + 4,5-dihydroxy-1-phenylcyclohexa-1,2-diene + NAD+ + HCl
Substrates: -
Products: -
Products: -
?
3,3'-dichlorobiphenyl + NADH + O2
5,6-dihydroxy-1-phenylcyclohexa-1,3-diene + 4,5-dihydroxy-1-phenylcyclohexa-1,2-diene + NAD+ + HCl
3,4'-dichlorobiphenyl + NADH + H+ + O2
3-chloro-5-(4-chlorophenyl)cyclohexa-3,5-diene-1,2-diol + 3-chloro-6-(3-chlorophenyl)cyclohexa-3,4-diene-1,2-diol
3,4,4'-trichlorobiphenyl + NADH + O2
?
-
Substrates: -
Products: -
Products: -
?
3,5',4'-trichlorobiphenyl + NADH + O2
?
-
Substrates: -
Products: -
Products: -
?
3-chlorobiphenyl + NADH + O2
cis-2',3'-dihydroxy-1'-(3-chlorophenyl)-cyclohexa-4',6'-diene + NAD+
4,4'-dichlorobiphenyl + NADH + H+ + O2
2,3-dihydroxy-4,4'-dichlorobiphenyl + NAD+
Substrates: -
Products: -
Products: -
?
4-methylbiphenyl + NADH + O2
2-hydroxy-6-oxo-6-[4-methylphenyl]-hexa-2,4-dienoic acid + NAD+
5,7-dihydroxyflavone + NADH + H+ + O2
2-(2,3-dihydroxyphenyl)-5,7-dihydroxy-chromen-4-one + NAD+
6,7-dihydro-5H-benzocycloheptene + NAD(P)H + O2
(-)-cis-(1R,2S)-dihydroxybenzocycloheptane + NAD(P)+
benzene + ?
?
-
Substrates: benzene is only a substrate for Pseudomonas pseudoalcaligenes strain 1072
Products: -
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?
biphenyl + NADH + H+ + O2
(1S,2R)-3-phenylcyclohexa-3,5-diene-1,2-diol + NAD+ + ?
-
Substrates: -
Products: -
Products: -
?
biphenyl + NADH + H+ + O2
cis-(2R,3S)-dihydroxy-1-phenylcyclohexa-4,6-diene + NAD+
-
Substrates: -
Products: -
Products: -
?
dibenzo-p-dioxine + NADH + O2
2,3,2'-trihydroxy-diphenylether + dibenzo-p-dioxine-dihydrodiol + NAD+
-
Substrates: -
Products: -
Products: -
?
dibenzofuran + NADH + O2
?
-
Substrates: dibenzofuran is a poor substrate
Products: -
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?
dibenzofurane + NADH + O2
2,2',3-trihydroxybiphenyl + dihydro-dihydroxy-dibenzofuran + NAD+
dibenzofurane + NADH + O2
monohydroxydibenzofuran + 2,3,2'-trihydroxybiphenyl + dibenzofuran-1,2-dihydrodiol + dibenzofuran-3,4-dihydrodiol + NAD+
-
Substrates: -
Products: -
Products: -
?
flavone + O2 + NAD(P)H
cis-flavone-2',3'-dihydrodiol + ?
-
Substrates: -
Products: -
Products: -
?
isoflavone + NADH + H+ + O2
isoflavone-cis-(2'R,3'S)-dihydrodiol + NAD+
-
Substrates: -
Products: -
Products: -
?
toluene + NAD(P)H + O2
?
-
Substrates: toluene is only a substrate for Pseudomonas pseudoalcaligenes strain 1072
Products: -
Products: -
?
(3R,4R)-cis-isoflavan-4-ol + NADH + H+ + O2
(3R,4R)-3-(7-oxabicyclo[4.1.0]hepta-1,3,5-trien-2-yl)-3,4-dihydro-2H-chromen-4-ol + NAD+
-
Substrates: -
Products: -
Products: -
?
(3R,4R)-cis-isoflavan-4-ol + NADH + H+ + O2
(3R,4R)-3-(7-oxabicyclo[4.1.0]hepta-1,3,5-trien-2-yl)-3,4-dihydro-2H-chromen-4-ol + NAD+
Pseudomonas oleovorans KF707
-
Substrates: -
Products: -
Products: -
?
(3R,4S)-trans-isoflavan-4-ol + NADH + H+ + O2
(3R,4S)-3-(7-oxabicyclo[4.1.0]hepta-1,3,5-trien-2-yl)-3,4-dihydro-2H-chromen-4-ol + NAD+
-
Substrates: -
Products: -
Products: -
?
(3R,4S)-trans-isoflavan-4-ol + NADH + H+ + O2
(3R,4S)-3-(7-oxabicyclo[4.1.0]hepta-1,3,5-trien-2-yl)-3,4-dihydro-2H-chromen-4-ol + NAD+
Pseudomonas oleovorans KF707
-
Substrates: -
Products: -
Products: -
?
(3S,4R)-trans-isoflavan-4-ol + NADH + H+ + O2
(3S,4R)-3-(7-oxabicyclo[4.1.0]hepta-1,3,5-trien-2-yl)-3,4-dihydro-2H-chromen-4-ol + NAD+
-
Substrates: -
Products: -
Products: -
?
(3S,4R)-trans-isoflavan-4-ol + NADH + H+ + O2
(3S,4R)-3-(7-oxabicyclo[4.1.0]hepta-1,3,5-trien-2-yl)-3,4-dihydro-2H-chromen-4-ol + NAD+
Pseudomonas oleovorans KF707
-
Substrates: -
Products: -
Products: -
?
2,2',3,3'-tetrachlorobiphenyl + NADH + H+ + O2
?
-
Substrates: -
Products: -
Products: -
?
2,2',3,3'-tetrachlorobiphenyl + NADH + H+ + O2
?
-
Substrates: -
Products: -
Products: -
?
2,2',3,3'-tetrachlorobiphenyl + NADH + H+ + O2
?
-
Substrates: -
Products: -
Products: -
?
2,2',3,3'-tetrachlorobiphenyl + NADH + O2
?
-
Substrates: -
Products: -
Products: -
?
2,2',3,3'-tetrachlorobiphenyl + NADH + O2
?
-
Substrates: -
Products: -
Products: -
?
2,2',5,5'-tetrachlorobiphenyl + NADH + H+ + O2
?
-
Substrates: -
Products: -
Products: -
?
2,2',5,5'-tetrachlorobiphenyl + NADH + H+ + O2
?
-
Substrates: -
Products: -
Products: -
?
2,2',5,5'-tetrachlorobiphenyl + NADH + H+ + O2
?
-
Substrates: -
Products: -
Products: -
?
2,2',5,5'-tetrachlorobiphenyl + NADH + H+ + O2
?
-
Substrates: -
Products: -
Products: -
?
2,2',5,5'-tetrachlorobiphenyl + NADH + O2
?
-
Substrates: -
Products: -
Products: -
?
2,2'-dibromobiphenyl + NADH + O2
2,3-dihydroxy-2'-bromobiphenyl + NAD+ + HBr
-
Substrates: -
Products: -
Products: -
?
2,2'-dibromobiphenyl + NADH + O2
2,3-dihydroxy-2'-bromobiphenyl + NAD+ + HBr
-
Substrates: -
Products: -
Products: -
?
2,2'-dichlorobiphenyl + NADH + H+ + O2
2,3-dihydroxy-2'-chlorobiphenyl + 3,4-dihydro-3,4-dihydroxy-2,2'-dichlorobiphenyl + NAD+ + HCl
-
Substrates: -
Products: -
Products: -
?
2,2'-dichlorobiphenyl + NADH + H+ + O2
2,3-dihydroxy-2'-chlorobiphenyl + 3,4-dihydro-3,4-dihydroxy-2,2'-dichlorobiphenyl + NAD+ + HCl
-
Substrates: -
Products: the ratio of 2,3-dihydroxy-2'-chlorobiphenyl to 3,4-dihydro-3,4-dihydroxy-2,2'-dichlorobiphenyl is: 90/10 for the wild-type enzyme, 40/60 for the mutant enzymes T335A/F336M, T335A/F336L/I341V and T335A/F336I,80/20 for mutant enzyme T335G, 85/15 for the mutant enzymes T335A and T335A/F336L
Products: the ratio of 2,3-dihydroxy-2'-chlorobiphenyl to 3,4-dihydro-3,4-dihydroxy-2,2'-dichlorobiphenyl is: 90/10 for the wild-type enzyme, 40/60 for the mutant enzymes T335A/F336M, T335A/F336L/I341V and T335A/F336I,80/20 for mutant enzyme T335G, 85/15 for the mutant enzymes T335A and T335A/F336L
?
2,2'-dichlorobiphenyl + NADH + H+ + O2
?
-
Substrates: -
Products: -
Products: -
?
2,2'-dichlorobiphenyl + NADH + H+ + O2
?
-
Substrates: -
Products: -
Products: -
?
2,2'-dichlorobiphenyl + NADH + H+ + O2
?
-
Substrates: wild-type enzyme
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?
2,2'-dichlorobiphenyl + NADH + H+ + O2
?
-
Substrates: -
Products: -
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?
2,2'-dichlorobiphenyl + NADH + H+ + O2
?
-
Substrates: -
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?
2,2'-dichlorobiphen