1.14.12.18: biphenyl 2,3-dioxygenase
This is an abbreviated version!
For detailed information about biphenyl 2,3-dioxygenase, go to the full flat file.
Word Map on EC 1.14.12.18
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1.14.12.18
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biphenyls
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polychlorinated
-
pseudoalcaligenes
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xenovorans
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chlorobiphenyls
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dihydrodiols
-
comamonas
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rieske-type
-
testosteroni
-
pcb-degrading
-
bpdos
-
pcb-contaminated
-
yanoikuyae
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2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoic
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2,3-dihydroxybiphenyls
-
biphenyl-degrading
-
cis-dihydrodiols
-
globerulus
-
ring-hydroxylating
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pnomenusa
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2,2\'-dichlorobiphenyl
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pandoraea
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polychlorobiphenyls
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biphenyl-utilizing
-
synthesis
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beijerinckia
-
chlorobenzoates
-
biphenyl-induced
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2,2\',5,5\'-tetrachlorobiphenyl
- 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
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2,2\',5,5\'-tetrachlorobiphenyl
Reaction
Synonyms
2,3-biphenyl dioxygenase, BDO, biphenyl 2, 3-dioxygenase, Biphenyl 2,3-dioxygenase, biphenyl dioxygenase, biphenyl-2,3-dioxygenase, BPDO, BPDOB356, BPDOCam-1, BPDOLB400, BPH, BPH dox, BphA, BphA1, BphA1A2, BphABC, BphABCD, BphAE, BPO, ThebphA1fA2f
ECTree
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Substrates Products
Substrates Products on EC 1.14.12.18 - biphenyl 2,3-dioxygenase
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REACTION DIAGRAM
(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+
-
-
-
-
?
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+
-
-
-
-
?
2,2',5,5'-tetrachlorobiphenyl + NADH + H+ + O2
3,4-dihydro-3,4-dihydroxy-2,2',5,5'-tetrachlorobiphenyl + NAD+
-
-
-
-
?
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
-
-
-
-
?
2,2'-dichlorobiphenyl + NADH + H+ + O2
2,3-dihydroxy-2'-chlorobiphenyl + NAD+ + HCl
-
poor substrate
-
-
?
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
-
-
-
-
?
2,3,2',3'-tetrachlorobiphenyl + NADH + H+ + O2
4,5-dihydro-4,5-dihydroxy-2,3,2',3'-tetrachlorobiphenyl + NAD+
-
oxygenated onto meta-para carbons 4 and 5
-
-
?
2,3,2',3'-tetrachlorobiphenyl + NADH + H+ + O2
cis-4,5-dihydro-4,5-dihydroxy-2,3,2',3'-tetrachlorobiphenyl + NAD+
-
-
-
-
?
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+
-
-
-
-
?
2,4,2',4'-tetrachlorobiphenyl + NADH + H+ + O2
2,3-dihydroxy-2',4,4'-trichlorobiphenyl + NAD+ + HCl
-
oxygenated principally onto vicinal ortho-meta carbons 2 and 3
-
-
?
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
-
-
-
-
?
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
-
-
-
-
?
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-dichlorobiphenyl + NADH + H+ + O2
2,6-dichloro-2',3'-dihydro-2',3'-dihydroxybiphenyl + ?
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
-
-
-
?
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-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+
-
-
-
?
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 + ?
?
-
benzene is only a substrate for Pseudomonas pseudoalcaligenes strain 1072
-
-
?
biphenyl + NADH + H+ + O2
(1S,2R)-3-phenylcyclohexa-3,5-diene-1,2-diol + NAD+ + ?
-
-
-
-
?
biphenyl + NADH + H+ + O2
cis-(2R,3S)-dihydroxy-1-phenylcyclohexa-4,6-diene + NAD+
-
-
-
-
?
dibenzo-p-dioxine + NADH + O2
2,3,2'-trihydroxy-diphenylether + dibenzo-p-dioxine-dihydrodiol + NAD+
-
-
-
-
?
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+
-
-
-
-
?
isoflavone + NADH + H+ + O2
isoflavone-cis-(2'R,3'S)-dihydrodiol + NAD+
-
-
-
-
?
toluene + NAD(P)H + O2
?
-
toluene is only a substrate for Pseudomonas pseudoalcaligenes strain 1072
-
-
?
(3R,4R)-3-(7-oxabicyclo[4.1.0]hepta-1,3,5-trien-2-yl)-3,4-dihydro-2H-chromen-4-ol + NAD+
-
-
-
-
?
(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
-
-
-
-
?
(3R,4S)-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+
Pseudomonas oleovorans KF707
-
-
-
-
?
(3S,4R)-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+
Pseudomonas oleovorans KF707
-
-
-
-
?
2,3-dihydroxy-2'-bromobiphenyl + NAD+ + HBr
-
-
-
-
?
2,2'-dibromobiphenyl + NADH + O2
2,3-dihydroxy-2'-bromobiphenyl + NAD+ + HBr
-
-
-
-
?
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 + 3,4-dihydro-3,4-dihydroxy-2,2'-dichlorobiphenyl + NAD+ + HCl
-
-
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
-
?
2,3-dihydroxy-2'-chlorobiphenyl + 3,4-dihydro-3,4-dihydroxy-2,2'-dichlorobiphenyl + NAD+
-
-
-
-
?
2,2'-dichlorobiphenyl + NADH + O2
2,3-dihydroxy-2'-chlorobiphenyl + 3,4-dihydro-3,4-dihydroxy-2,2'-dichlorobiphenyl + NAD+
Pseudomonas oleovorans KF707
-
-
-
-
?
2,3-dihydroxy-2'-chlorobiphenyl + NAD+ + HCl
-
-
-
-
?
2,2'-dichlorobiphenyl + NADH + O2
2,3-dihydroxy-2'-chlorobiphenyl + NAD+ + HCl
-
-
-
-
?
5,6-dihydroxy-1-phenylcyclohexa-1,3-diene + 2,3-dihydroxy-2'-chlorobiphenyl + NAD+ + HCl
-
-
-
-
?
2,2'-dichlorobiphenyl + NADH + O2
5,6-dihydroxy-1-phenylcyclohexa-1,3-diene + 2,3-dihydroxy-2'-chlorobiphenyl + NAD+ + HCl
-
-
-
-
?
2,2'-dichlorobiphenyl + NADH + O2
5,6-dihydroxy-1-phenylcyclohexa-1,3-diene + 2,3-dihydroxy-2'-chlorobiphenyl + NAD+ + HCl
-
-
-
-
?
2,2'-dichlorobiphenyl + NADH + O2
5,6-dihydroxy-1-phenylcyclohexa-1,3-diene + 2,3-dihydroxy-2'-chlorobiphenyl + NAD+ + HCl
-
-
-
-
?
2,2'-dichlorobiphenyl + NADH + O2
5,6-dihydroxy-1-phenylcyclohexa-1,3-diene + 2,3-dihydroxy-2'-chlorobiphenyl + NAD+ + HCl
-
-
-
-
?
2,3-dihydroxy-2'-fluorobiphenyl + 5,6-dihydroxy-2,2'-difluorobiphenyl + NAD+ + HF
-
-
-
-
?
2,2'-difluorobiphenyl + NADH + O2
2,3-dihydroxy-2'-fluorobiphenyl + 5,6-dihydroxy-2,2'-difluorobiphenyl + NAD+ + HF
-
-
-
-
?
2,3,2'-trihydroxybiphenyl + trihydroxybiphenyl + NAD+
-
-
-
-
?
2,2'-dihydroxybiphenyl + NADH + O2
2,3,2'-trihydroxybiphenyl + trihydroxybiphenyl + NAD+
-
-
-
-
?
2,3-dihydroxy-2'-nitrobiphenyl + NAD+ + NO2
-
-
-
-
?
2,2'-dinitrobiphenyl + NADH + O2
2,3-dihydroxy-2'-nitrobiphenyl + NAD+ + NO2
-
-
-
-
?
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 + 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-dihydroxy-4'-chlorobiphenyl + NAD+ + HCl
-
-
-
-
?
2,4'-dichlorobiphenyl + NADH + O2
2,3-dihydroxy-4'-chlorobiphenyl + NAD+ + HCl
-
-
-
-
?
2,3-dihydro-2,3-dihydroxy-2',4,4'-trichlorobiphenyl + NAD+
-
-
-
-
?
2,4,4'-trichlorobiphenyl + NADH + H+ + O2
2,3-dihydro-2,3-dihydroxy-2',4,4'-trichlorobiphenyl + NAD+
-
-
-
-
?
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',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
-
-
-
-
?
cis-2',3'-dihydroxy-1'-(2,5-dichlorophenyl)-cyclohexa-4',6'-diene + 3,4-dihydroxy-1-phenylcyclohexa-1,5-diene + NAD+ + HCl
-
no 3,4-dihydrodiol as product
-
-
?
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
-
-
-
-
?
2,5-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
-
-
-
-
?
2,5-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
-
-
-
-
?
2,5-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-dichloro-2',3'-dihydro-2',3'-dihydroxybiphenyl + ?
-
-
-
-
?
2,6-dichlorobiphenyl + NADH + H+ + O2
2,6-dichloro-2',3'-dihydro-2',3'-dihydroxybiphenyl + ?
-
-
-
-
?
cis-2',3'-dihydroxy-1'-(2-chlorophenyl)-cyclohexa-4',6'-diene + catechol + NAD+
-
-
-
-
?
2-chlorobiphenyl + NADH + O2
cis-2',3'-dihydroxy-1'-(2-chlorophenyl)-cyclohexa-4',6'-diene + catechol + NAD+
-
-
-
-
?
2-chlorobiphenyl + NADH + O2
cis-2',3'-dihydroxy-1'-(2-chlorophenyl)-cyclohexa-4',6'-diene + catechol + NAD+
-
no catechol formation
-
-
?
2-chlorobiphenyl + NADH + O2
cis-2',3'-dihydroxy-1'-(2-chlorophenyl)-cyclohexa-4',6'-diene + catechol + NAD+
-
no catechol formation
-
-
?
?
-
ortho-meta-oxygenation, hydroxylation on the non-substituted ring
-
-
?
2-hydroxy-3,5-dichlorobiphenyl + NADH + H+ + O2
?
-
ortho-meta-oxygenation, hydroxylation on the non-substituted ring
-
-
?
2-hydroxy-3,5-dichlorobiphenyl + NADH + H+ + O2
?
-
ortho-meta-oxygenation, hydroxylation on the non-substituted ring
-
-
?
5-(3-chloro-2-hydroxyphenyl)-6-hydroxy-3-cyclohexen-1-one + NAD+
-
ortho-meta-oxygenation, hydroxylation on the non-substituted ring
+ minor amounts of dihydroxybiphenyl, generated by the rearrangement of cis-2,3-dihydro-2,3-dihydroxy-2'-hydroxy-3'-chlorobiphenyl and minor amounts of cis-2,3-dihydro-2,3-dihydroxy-2'-hydroxy-3'-chlorobiphenyl and 2-hydroxy-3-chloro-2',3'-dihydroxybiphenyl. 5-(3-chloro-2-hydroxyphenyl)-6-hydroxy-3-cyclohexen-1-one is likely generated from the rearrangement of cis-2,3-dihydro-2,3-dihydroxy-2'-hydroxy-3'-chlorobiphenyl
-
?
2-hydroxy-3-chlorobiphenyl + NADH + H+ + O2
5-(3-chloro-2-hydroxyphenyl)-6-hydroxy-3-cyclohexen-1-one + NAD+
-
ortho-meta-oxygenation, hydroxylation on the non-substituted ring
+ minor amounts of dihydroxybiphenyl, generated by the rearrangement of cis-2,3-dihydro-2,3-dihydroxy-2'-hydroxy-3'-chlorobiphenyl and minor amounts of cis-2,3-dihydro-2,3-dihydroxy-2'-hydroxy-3'-chlorobiphenyl and 2-hydroxy-3-chloro-2',3'-dihydroxybiphenyl. 5-(3-chloro-2-hydroxyphenyl)-6-hydroxy-3-cyclohexen-1-one is likely generated from the rearrangement of cis-2,3-dihydro-2,3-dihydroxy-2'-hydroxy-3'-chlorobiphenyl
-
?
2-hydroxy-3-chlorobiphenyl + NADH + H+ + O2
5-(3-chloro-2-hydroxyphenyl)-6-hydroxy-3-cyclohexen-1-one + NAD+
-
ortho-meta-oxygenation, hydroxylation on the non-substituted ring
+ minor amounts of dihydroxybiphenyl, generated by the rearrangement of cis-2,3-dihydro-2,3-dihydroxy-2'-hydroxy-3'-chlorobiphenyl and minor amounts of cis-2,3-dihydro-2,3-dihydroxy-2'-hydroxy-3'-chlorobiphenyl and 2-hydroxy-3-chloro-2',3'-dihydroxybiphenyl. 5-(3-chloro-2-hydroxyphenyl)-6-hydroxy-3-cyclohexen-1-one is likely generated from the rearrangement of cis-2,3-dihydro-2,3-dihydroxy-2'-hydroxy-3'-chlorobiphenyl
-
?
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+
-
ortho-meta-oxygenation, hydroxylation on the non-substituted ring
minor amounts of cis-2,3-dihydro-2,3-dihydroxy-2'-hydroxy-5'-chlorobiphenyl are also found as well as 2-hydroxy-5-chloro-2',3'-dihydroxybiphenyl which is most likely generated by spontaneous rearrangement and dehydrogenation of cis-2,3-dihydro-2,3-dihydroxy-2'-hydroxy-5'-chlorobiphenyl. 5-(5-chloro-2-hydroxyphenyl)-6-hydroxy-3-cyclohexene-1-oneis likely to be generated from rearrangement of cis-2,3-dihydro-2,3-dihydroxy-2'-hydroxy-5'-chlorobiphenyl. 2,2'-Dihydroxy-5-chlorobiphenyl and 2,3'-dihydroxy-5-chlorobiphenyl are also generated by the loss of OH and rearrangement of cis-2,3-dihydro-2,3-dihydroxy-2'-hydroxy-5'-chlorobiphenyl
-
?
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+
-
ortho-meta-oxygenation, hydroxylation on the non-substituted ring
minor amounts of cis-2,3-dihydro-2,3-dihydroxy-2'-hydroxy-5'-chlorobiphenyl are also found as well as 2-hydroxy-5-chloro-2',3'-dihydroxybiphenyl which is most likely generated by spontaneous rearrangement and dehydrogenation of cis-2,3-dihydro-2,3-dihydroxy-2'-hydroxy-5'-chlorobiphenyl. 5-(5-chloro-2-hydroxyphenyl)-6-hydroxy-3-cyclohexene-1-oneis likely to be generated from rearrangement of cis-2,3-dihydro-2,3-dihydroxy-2'-hydroxy-5'-chlorobiphenyl. 2,2'-Dihydroxy-5-chlorobiphenyl and 2,3'-dihydroxy-5-chlorobiphenyl are also generated by the loss of OH and rearrangement of cis-2,3-dihydro-2,3-dihydroxy-2'-hydroxy-5'-chlorobiphenyl
-
?
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+
-
ortho-meta-oxygenation, hydroxylation on the non-substituted ring
minor amounts of cis-2,3-dihydro-2,3-dihydroxy-2'-hydroxy-5'-chlorobiphenyl are also found as well as 2-hydroxy-5-chloro-2',3'-dihydroxybiphenyl which is most likely generated by spontaneous rearrangement and dehydrogenation of cis-2,3-dihydro-2,3-dihydroxy-2'-hydroxy-5'-chlorobiphenyl. 5-(5-chloro-2-hydroxyphenyl)-6-hydroxy-3-cyclohexene-1-oneis likely to be generated from rearrangement of cis-2,3-dihydro-2,3-dihydroxy-2'-hydroxy-5'-chlorobiphenyl. 2,2'-Dihydroxy-5-chlorobiphenyl and 2,3'-dihydroxy-5-chlorobiphenyl are also generated by the loss of OH and rearrangement of cis-2,3-dihydro-2,3-dihydroxy-2'-hydroxy-5'-chlorobiphenyl
-
?
5,6-dihydroxy-1-phenylcyclohexa-1,3-diene + 4,5-dihydroxy-1-phenylcyclohexa-1,2-diene + NAD+ + HCl
-
-
-
-
?
3,3'-dichlorobiphenyl + NADH + O2
5,6-dihydroxy-1-phenylcyclohexa-1,3-diene + 4,5-dihydroxy-1-phenylcyclohexa-1,2-diene + NAD+ + HCl
-
-
-
-
?
3,3'-dichlorobiphenyl + NADH + O2
5,6-dihydroxy-1-phenylcyclohexa-1,3-diene + 4,5-dihydroxy-1-phenylcyclohexa-1,2-diene + NAD+ + HCl
-
-
-
-
?
3,3'-dichlorobiphenyl + NADH + O2
5,6-dihydroxy-1-phenylcyclohexa-1,3-diene + 4,5-dihydroxy-1-phenylcyclohexa-1,2-diene + NAD+ + HCl
-
poor substrate
-
-
?
3,3'-dichlorobiphenyl + NADH + O2
5,6-dihydroxy-1-phenylcyclohexa-1,3-diene + 4,5-dihydroxy-1-phenylcyclohexa-1,2-diene + NAD+ + HCl
-
-
-
-
?
3,3'-dichlorobiphenyl + NADH + O2
5,6-dihydroxy-1-phenylcyclohexa-1,3-diene + 4,5-dihydroxy-1-phenylcyclohexa-1,2-diene + NAD+ + HCl
-
-
-
-
?
3,3'-dichlorobiphenyl + NADH + O2
5,6-dihydroxy-1-phenylcyclohexa-1,3-diene + 4,5-dihydroxy-1-phenylcyclohexa-1,2-diene + NAD+ + HCl
-
-
-
-
?
5,6-dihydroxy-3,4'-dichlorobiphenyl + NAD(P)+
-
-
-
-
?
3,4'-dichlorobiphenyl + NAD(P)H + O2
5,6-dihydroxy-3,4'-dichlorobiphenyl + NAD(P)+
-
-
-
-
?
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'-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
-
-
-
-
?
cis-2',3'-dihydroxy-1'-(3-chlorophenyl)-cyclohexa-4',6'-diene + NAD+
-
-
-
-
?
3-chlorobiphenyl + NADH + O2
cis-2',3'-dihydroxy-1'-(3-chlorophenyl)-cyclohexa-4',6'-diene + NAD+
-
-
-
-
?
3-chlorobiphenyl + NADH + O2
cis-2',3'-dihydroxy-1'-(3-chlorophenyl)-cyclohexa-4',6'-diene + NAD+
-
-
-
-
?
3-chlorobiphenyl + NADH + O2
cis-2',3'-dihydroxy-1'-(3-chlorophenyl)-cyclohexa-4',6'-diene + NAD+
-
-
-
-
?
2,3-dihydroxy-4,4'-dichlorobiphenyl + NAD(P)+
-
-
-
-
?
4,4'-dichlorobiphenyl + NAD(P)H + O2
2,3-dihydroxy-4,4'-dichlorobiphenyl + NAD(P)+
Pseudomonas oleovorans KF707
-
-
-
-
?
4,4'-dichlorobiphenyl + NAD(P)H + O2
2,3-dihydroxy-4,4'-dichlorobiphenyl + NAD(P)+
-
-
-
-
?
4,4'-dichlorobiphenyl + NAD(P)H + O2
2,3-dihydroxy-4,4'-dichlorobiphenyl + NAD(P)+
-
-
-
-
?
2',3'-dihydrodiol-4-chlorobiphenyl + NAD+
-
-
-
-
?
4-chlorobiphenyl + NADH + O2
2',3'-dihydrodiol-4-chlorobiphenyl + NAD+
-
-
-
-
?
4-chlorobiphenyl + NADH + O2
2',3'-dihydrodiol-4-chlorobiphenyl + NAD+
-
-
-
-
?
4-chlorobiphenyl + NADH + O2
2',3'-dihydrodiol-4-chlorobiphenyl + NAD+
-
-
-
-
?
2-hydroxy-6-oxo-6-[4-methylphenyl]-hexa-2,4-dienoic acid + NAD+
-
-
-
-
?
4-methylbiphenyl + NADH + O2
2-hydroxy-6-oxo-6-[4-methylphenyl]-hexa-2,4-dienoic acid + NAD+
Pseudomonas oleovorans KF707
-
-
-
-
?
2-(2,3-dihydroxyphenyl)-5,7-dihydroxy-chromen-4-one + NAD+
-
BphA1 (1-22) and BphA1 (2-2), expression of the mutants in together with bphA2A3A4B from strain KF707
-
-
?
5,7-dihydroxyflavone + NADH + H+ + O2
2-(2,3-dihydroxyphenyl)-5,7-dihydroxy-chromen-4-one + NAD+
-
BphA1 (1-22) and BphA1 (2-2), expression of the mutants in together with bphA2A3A4B from strain KF707
-
-
?
(-)-cis-(1R,2S)-dihydroxybenzocycloheptane + NAD(P)+
-
-
-
-
?
6,7-dihydro-5H-benzocycloheptene + NAD(P)H + O2
(-)-cis-(1R,2S)-dihydroxybenzocycloheptane + NAD(P)+
-
-
-
-
?
2-(2,3-dihydroxyphenyl)-7-hydroxy-chromen-4-one + NAD+
-
BphA1 (1-22) and BphA1 (2-2), expression of the mutants together with bphA2A3A4B from strain KF707
-
-
?
7-hydroxyflavone + NADH + H+ + O2
2-(2,3-dihydroxyphenyl)-7-hydroxy-chromen-4-one + NAD+
-
BphA1 (1-22) and BphA1 (2-2), expression of the mutants together with bphA2A3A4B from strain KF707
-
-
?
(1S,2R)-dihydroxy-3-phenylcyclohexa-3,5-diene + NAD(P)+
-
-
-
-
?
biphenyl + NAD(P)H + O2
(1S,2R)-dihydroxy-3-phenylcyclohexa-3,5-diene + NAD(P)+
-
-
-
-
?
biphenyl + NAD(P)H + O2
2,3-dihydro-dihydroxybiphenyl + NAD(P)+
-
-
-
-
?
biphenyl + NAD(P)H + O2
2,3-dihydro-dihydroxybiphenyl + NAD(P)+
-
-
-
-
?
biphenyl + NAD(P)H + O2
2,3-dihydro-dihydroxybiphenyl + NAD(P)+
-
-
-
-
?
cis-biphenyl 2,3-dihydrodiol + NAD(P)+
-
-
-
-
?
biphenyl + NAD(P)H + O2
cis-biphenyl 2,3-dihydrodiol + NAD(P)+
-
-
-
-
?
biphenyl + NAD(P)H + O2
cis-biphenyl 2,3-dihydrodiol + NAD(P)+
Pseudomonas oleovorans KF707
-
-
-
-
?
biphenyl + NAD(P)H + O2
cis-biphenyl 2,3-dihydrodiol + NAD(P)+
-
-
-
-
?
biphenyl + NAD(P)H + O2
cis-biphenyl 2,3-dihydrodiol + NAD(P)+
-
-
-
-
?
biphenyl + NAD(P)H + O2
cis-biphenyl 2,3-dihydrodiol + NAD(P)+
-
-
-
-
?
biphenyl + NAD(P)H + O2
cis-biphenyl 2,3-dihydrodiol + NAD(P)+
-
-
-
-
?
(1S,2R)-3-phenylcyclohexa-3,5-diene-1,2-diol + NAD+
-
-
-
-
?
biphenyl + NADH + H+ + O2
(1S,2R)-3-phenylcyclohexa-3,5-diene-1,2-diol + NAD+
-
-
-
-
?
biphenyl + NADH + H+ + O2
(1S,2R)-3-phenylcyclohexa-3,5-diene-1,2-diol + NAD+
-
-
-
?
biphenyl + NADH + H+ + O2
(1S,2R)-3-phenylcyclohexa-3,5-diene-1,2-diol + NAD+
-
-
-
-
?
biphenyl + NADH + H+ + O2
(1S,2R)-3-phenylcyclohexa-3,5-diene-1,2-diol + NAD+
-
-
-
?
biphenyl + NADH + H+ + O2
(1S,2R)-3-phenylcyclohexa-3,5-diene-1,2-diol + NAD+
-
-
-
-
?
biphenyl + NADH + H+ + O2
(1S,2R)-3-phenylcyclohexa-3,5-diene-1,2-diol + NAD+
-
-
-
-
?
2,3-dihydro-dihydroxybiphenyl + NAD+
-
-
-
?
biphenyl + NADH + H+ + O2
2,3-dihydro-dihydroxybiphenyl + NAD+
-
-
-
?
biphenyl + NADH + H+ + O2
2,3-dihydro-dihydroxybiphenyl + NAD+
-
-
-
-
?
biphenyl + NADH + H+ + O2
2,3-dihydro-dihydroxybiphenyl + NAD+
-
-
-
-
?
biphenyl + NADH + H+ + O2
2,3-dihydro-dihydroxybiphenyl + NAD+
Pseudomonas oleovorans KF707
-
-
-
-
?
biphenyl + NADH + O2
cis-biphenyl 2,3-dihydrodiol + NAD+
-
-
-
-
?
3-hydroxycarbazole + NAD+
-
no products with carbazole detected
-
-
?
carbazole + NADH + O2
3-hydroxycarbazole + NAD+
-
no products with carbazole detected
-
-
?
carbazole + NADH + O2
3-hydroxycarbazole + NAD+
-
formation of an unstable cis-carbazole-3,4-dihydrodiol is proposed
-
-
?
carbazole + NADH + O2
3-hydroxycarbazole + NAD+
-
formation of an unstable cis-carbazole-3,4-dihydrodiol is proposed
-
-
?
2,2',3-trihydroxybiphenyl ether + NAD+
-
-
-
-
?
dibenzo-p-dioxin + NADH + O2
2,2',3-trihydroxybiphenyl ether + NAD+
-
-
-
-
?
2,2',3-trihydroxybiphenyl + dihydro-dihydroxy-dibenzofuran + NAD+
-
-
+ small amounts of 2,2',3-trihydroxybiphenyl. 2,2',3-dihydroxybiphenyl results from angular oxygenation, dihydro-dihydroxy-dibenzofuran results from lateral oxygenation
-
?
dibenzofurane + NADH + O2
2,2',3-trihydroxybiphenyl + dihydro-dihydroxy-dibenzofuran + NAD+
-
-
+ small amounts of 2,2',3-trihydroxybiphenyl. 2,2',3-dihydroxybiphenyl results from angular oxygenation, dihydro-dihydroxy-dibenzofuran results from lateral oxygenation
-
?
cis-flavone-2',3'-dihydrodiol + ?
-
the flavone metabolite is 2-[(5S,6R)-5,6-dihydroxycyclohexa-1,3-dienyl]-4H-chromen-4-one
-
-
?
flavone + O2 + NADH + H+
cis-flavone-2',3'-dihydrodiol + ?
Pseudomonas oleovorans KF707
-
the flavone metabolite is 2-[(5S,6R)-5,6-dihydroxycyclohexa-1,3-dienyl]-4H-chromen-4-one
-
-
?
2',3'-dihydro-2',3'-cis-dihydroxyflavone + NAD+
-
biphenyl dioxygenase induces 2',3'-cis-dihydroxylation of the B-ring of isoflavone, the isoflavone metabolite is 3-[(5S,6R)-5,6-dihydroxycyclohexa-1,3-dienyl]-4H-chromen-4-one
-
-
?
isoflavone + O2 + NADH + H+
2',3'-dihydro-2',3'-cis-dihydroxyflavone + NAD+
Pseudomonas oleovorans KF707
-
biphenyl dioxygenase induces 2',3'-cis-dihydroxylation of the B-ring of isoflavone, the isoflavone metabolite is 3-[(5S,6R)-5,6-dihydroxycyclohexa-1,3-dienyl]-4H-chromen-4-one
-
-
?
cis-naphthalene 1,2-dihydrodiol + NADP+
-
poor substrate
-
-
?
naphthalene + NADPH + O2
cis-naphthalene 1,2-dihydrodiol + NADP+
-
poor substrate
-
-
?
1,2-dihydro-1,2-dihydroxyphenazine + NAD+
-
-
-
-
?
phenazine + NADH + H+ + O2
1,2-dihydro-1,2-dihydroxyphenazine + NAD+
-
-
-
-
?
additional information
?
-
-
enzyme of biphenyl catabolic pathway
-
-
?
additional information
?
-
-
no activity with 4,4'-dichlorobiphenyl and 2,2',5,5'-tetrachlorobiphenyl
-
-
?
additional information
?
-
-
the strain LY402 shows polychlorinated biphenyls degradation abilities of BphA1, molecular simulation and ligand docking studies, overview
-
-
?
additional information
?
-
-
the strain LY402 shows polychlorinated biphenyls degradation abilities of BphA1, molecular simulation and ligand docking studies, overview
-
-
?
additional information
?
-
-
no activity on toluene and benzene
-
-
?
additional information
?
-
-
biphenyl pathway of strain LB400 oxidizes an unusually wide range of polychlorinated biphenyl congeners and BphA is able to dihydroxylate from mono-chlorobiphenyls to 2,3,4,5,2',5'-hexachlorobiphenyl, is able to oxidize other substituted biphenyls, unsubstituted dibenzofuran and dibenzodioxin and is also able to transform different isoflavonoids. A hybrid BphA based on the LB400 enzyme but harboring the core segment of an oxygenase from Pseudomonas sp. strain B4-Magdeburg shows (depending on the congener considered) complementing or improved degradative properties. BphA mutants with increased catalytic turnover on polychlorinated biphenyls, that are recalcitrant for the parental BphA from strain LB400
-
-
?
additional information
?
-
-
overview on polychlorinated biphenyls
-
-
?
additional information
?
-
-
the enzyme also shows monooxygenase activity by converting 2(R)- and 2(S)-flavanone to their corresponding epoxides, whereby the epoxide bond is formed between C2' and C3' on the B ring of the flavanone
-
-
?
additional information
?
-
-
the enzyme does not produce metabolites from 2'-hydroxyflavanone, 3'-hydroxyflavanone, and naringenin
-
-
?
additional information
?
-
-
BDO shows stereoselective preference to the stereoisomers of isoflavan-4-ol in the order (3S,4S)-cis-isoflavan-4-ol > (3R,4S)-transisoflavan-4-ol > (3S,4R)-trans-isoflavan-4-ol > (3R,4R)-cisisoflavan-4-ol
-
-
?
additional information
?
-
Pseudomonas oleovorans KF707
-
overview on polychlorinated biphenyls
-
-
?
additional information
?
-
Pseudomonas oleovorans KF707
-
the enzyme also shows monooxygenase activity by converting 2(R)- and 2(S)-flavanone to their corresponding epoxides, whereby the epoxide bond is formed between C2' and C3' on the B ring of the flavanone
-
-
?
additional information
?
-
Pseudomonas oleovorans KF707
-
the enzyme does not produce metabolites from 2'-hydroxyflavanone, 3'-hydroxyflavanone, and naringenin
-
-
?
additional information
?
-
Pseudomonas oleovorans KF707
-
BDO shows stereoselective preference to the stereoisomers of isoflavan-4-ol in the order (3S,4S)-cis-isoflavan-4-ol > (3R,4S)-transisoflavan-4-ol > (3S,4R)-trans-isoflavan-4-ol > (3R,4R)-cisisoflavan-4-ol
-
-
?
additional information
?
-
-
trans-chalcone is converted into 3-(2,3-dihydroxyphenyl)-1-phenylpropan-1-one and further into 1,3-bis-(2,3-dihydroxyphenyl)-propan-1-one
-
-
?
additional information
?
-
-
trans-chalcone is converted into 3-(2,3-dihydroxyphenyl)-1-phenylpropan-1-one and further into 1,3-bis-(2,3-dihydroxyphenyl)-propan-1-one
-
-
?
additional information
?
-
-
no substrates are benzene, toluene, 2,5-dichlorotoluene, carbazole and dibenzothiophene
-
-
?
additional information
?
-
-
overview on polychlorinated biphenyls
-
-
?
additional information
?
-
-
overview on polychlorinated biphenyls
-
-
?
additional information
?
-
-
no substrates are benzene, toluene, 2,5-dichlorotoluene, carbazole and dibenzothiophene
-
-
?
additional information
?
-
-
overview on polychlorinated biphenyls
-
-
?
additional information
?
-
-
Phe378 and Phe384 are near the substrate inside the catalytic pocket and thus likely interact with it
-
-
?
additional information
?
-
-
biphenyl 2,3-dioxygenase is responsible for the ability of Sphingobium yanoikuyae strain B1 to dihydroxylate large aromatic compounds, such as chrysene and benzo[a]pyrene
-
-
?
additional information
?
-
-
a single multicomponent dioxygenase enzyme is involved in the initial oxidation of both biphenyl and naphthalene in Sphingobium yanoikuyae strain B1
-
-
?
additional information
?
-
-
biphenyl 2,3-dioxygenase is responsible for the ability of Sphingobium yanoikuyae strain B1 to dihydroxylate large aromatic compounds, such as chrysene and benzo[a]pyrene
-
-
?
additional information
?
-
-
a single multicomponent dioxygenase enzyme is involved in the initial oxidation of both biphenyl and naphthalene in Sphingobium yanoikuyae strain B1
-
-
?