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(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',3,3'-tetrachlorobiphenyl + NADH + H+ + O2
?
2,2',3,3'-tetrachlorobiphenyl + NADH + O2
?
2,2',5,5'-tetrachlorobiphenyl + NADH + H+ + O2
3,4-dihydro-3,4-dihydroxy-2,2',5,5'-tetrachlorobiphenyl + NAD+
-
-
-
?
2,2',5,5'-tetrachlorobiphenyl + NADH + H+ + O2
?
2,2',5,5'-tetrachlorobiphenyl + NADH + O2
?
2,2'-dibromobiphenyl + NADH + H+ + O2
?
2,2'-dibromobiphenyl + NADH + O2
2,3-dihydroxy-2'-bromobiphenyl + NAD+ + HBr
2,2'-dichlorobiphenyl + NADH + H+ + O2
2,3-dihydroxy-2'-chlorobiphenyl + 3,4-dihydro-3,4-dihydroxy-2,2'-dichlorobiphenyl + NAD+
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+
-
poor substrate
-
?
2,2'-dichlorobiphenyl + NADH + H+ + O2
?
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
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'-difluorobiphenyl + NADH + H+ + O2
?
2,2'-difluorobiphenyl + NADH + O2
2,3-dihydroxy-2'-fluorobiphenyl + 5,6-dihydroxy-2,2'-difluorobiphenyl + NAD+ + HF
2,2'-dihydroxybiphenyl + NADH + H+ + O2
?
2,2'-dihydroxybiphenyl + NADH + O2
2,3,2'-trihydroxybiphenyl + trihydroxybiphenyl + NAD+
2,2'-dinitrobiphenyl + NADH + H+ + O2
?
-
-
-
?
2,2'-dinitrobiphenyl + NADH + O2
2,3-dihydroxy-2'-nitrobiphenyl + NAD+ + NO2
2,3',4'-trichlorobiphenyl + NADH + O2
?
-
-
-
?
2,3',4-trichlorobiphenyl + NADH + H+ + O2
?
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+
-
-
-
?
2,3,4'-trichlorobiphenyl + NADH + H+ + O2
?
2,3,4'-trichlorobiphenyl + NADH + O2
?
-
-
-
?
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'-dichlorobiphenyl + NADH + O2
2,3-dihydroxy-4'-chlorobiphenyl + NAD+ + HCl
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
-
-
-
?
2,5,4'-trichlorobiphenyl + NADH + O2
?
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
?
-
-
-
?
2,6-dichlorobiphenyl + NADH + H+ + O2
2,6-dichloro-2',3'-dihydro-2',3'-dihydroxybiphenyl + ?
2,6-dichlorobiphenyl + NADH + H+ + O2
?
-
poor substrate
-
?
2-chlorobiphenyl + NADH + O2
cis-2',3'-dihydroxy-1'-(2-chlorophenyl)-cyclohexa-4',6'-diene + catechol + NAD+
2-hydroxy-3,5-dichlorobiphenyl + NADH + H+ + O2
?
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 + H+ + O2
?
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
?
-
-
-
?
3,4'-dichlorobiphenyl + NAD(P)H + O2
5,6-dihydroxy-3,4'-dichlorobiphenyl + NAD(P)+
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
?
-
-
-
?
3,5',4'-trichlorobiphenyl + NADH + O2
?
-
-
-
?
3-chlorobiphenyl + NADH + O2
cis-2',3'-dihydroxy-1'-(3-chlorophenyl)-cyclohexa-4',6'-diene + NAD+
4,4'-dichlorobiphenyl + NAD(P)H + O2
2,3-dihydroxy-4,4'-dichlorobiphenyl + NAD(P)+
4,4'-dichlorobiphenyl + NADH + H+ + O2
2,3-dihydroxy-4,4'-dichlorobiphenyl + NAD+
-
-
?
4,4'-dichlorobiphenyl + NADH + H+ + O2
?
4-chlorobiphenyl + NADH + O2
2',3'-dihydrodiol-4-chlorobiphenyl + 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)+
6-hydroxyflavanone + O2 + NAD(P)H
?
7-hydroxyflavanone + O2 + NAD(P)H
?
7-hydroxyflavone + NADH + H+ + O2
2-(2,3-dihydroxyphenyl)-7-hydroxy-chromen-4-one + NAD+
benzene + ?
?
-
benzene is only a substrate for Pseudomonas pseudoalcaligenes strain 1072
-
?
benzo[a]pyrene + NADH + O2
?
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
cis-biphenyl 2,3-dihydrodiol + NAD(P)+
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
2,3-dihydro-dihydroxybiphenyl + NAD+
biphenyl + NADH + H+ + O2
?
biphenyl + NADH + H+ + O2
cis-(2R,3S)-dihydroxy-1-phenylcyclohexa-4,6-diene + NAD+
-
-
-
?
biphenyl + NADH + O2
cis-biphenyl 2,3-dihydrodiol + NAD+
carbazole + NADH + O2
3-hydroxycarbazole + NAD+
dibenzo-p-dioxin + NADH + O2
2,2',3-trihydroxybiphenyl ether + NAD+
dibenzo-p-dioxine + NADH + O2
2,3,2'-trihydroxy-diphenylether + dibenzo-p-dioxine-dihydrodiol + NAD+
-
-
-
?
dibenzofuran + NADH + O2
?
-
dibenzofuran is a poor substrate
-
?
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+
-
-
-
?
diphenylmethane + NADH + O2
?
-
-
-
?
ethylbenzene + ?
?
-
-
-
?
ethylbenzene + NADH + O2
?
-
-
-
?
flavone + O2 + NAD(P)H
cis-flavone-2',3'-dihydrodiol + ?
-
-
-
?
flavone + O2 + NADH + H+
cis-flavone-2',3'-dihydrodiol + ?
isoflavone + NADH + H+ + O2
isoflavone-cis-(2'R,3'S)-dihydrodiol + NAD+
-
-
-
?
isoflavone + O2 + NADH + H+
2',3'-dihydro-2',3'-cis-dihydroxyflavone + NAD+
naphthalene + NADH + O2
?
naphthalene + NADPH + O2
cis-naphthalene 1,2-dihydrodiol + NADP+
phenanthrene + NADH + O2
?
phenazine + NADH + H+ + O2
1,2-dihydro-1,2-dihydroxyphenazine + NAD+
toluene + NAD(P)H + O2
?
-
toluene is only a substrate for Pseudomonas pseudoalcaligenes strain 1072
-
?
additional information
?
-
(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,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+
-
-
-
?
(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,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+
-
-
-
?
2,2',3,3'-tetrachlorobiphenyl + NADH + H+ + O2

?
-
-
-
?
2,2',3,3'-tetrachlorobiphenyl + NADH + H+ + O2
?
-
-
-
?
2,2',3,3'-tetrachlorobiphenyl + NADH + H+ + O2
?
-
-
-
?
2,2',3,3'-tetrachlorobiphenyl + NADH + O2

?
-
-
-
?
2,2',3,3'-tetrachlorobiphenyl + NADH + O2
?
-
-
-
?
2,2',3,3'-tetrachlorobiphenyl + NADH + O2
?
-
-
-
?
2,2',5,5'-tetrachlorobiphenyl + NADH + H+ + O2

?
-
-
-
?
2,2',5,5'-tetrachlorobiphenyl + NADH + H+ + O2
?
-
-
-
?
2,2',5,5'-tetrachlorobiphenyl + NADH + H+ + O2
?
-
-
-
?
2,2',5,5'-tetrachlorobiphenyl + NADH + H+ + O2
?
-
-
-
?
2,2',5,5'-tetrachlorobiphenyl + NADH + O2

?
-
-
-
?
2,2',5,5'-tetrachlorobiphenyl + NADH + O2
?
-
-
-
?
2,2'-dibromobiphenyl + NADH + H+ + O2

?
-
-
-
?
2,2'-dibromobiphenyl + NADH + H+ + O2
?
-
-
-
?
2,2'-dibromobiphenyl + NADH + O2

2,3-dihydroxy-2'-bromobiphenyl + NAD+ + HBr
-
-
-
?
2,2'-dibromobiphenyl + NADH + O2
2,3-dihydroxy-2'-bromobiphenyl + NAD+ + HBr
-
-
-
?
2,2'-dichlorobiphenyl + NADH + H+ + O2

2,3-dihydroxy-2'-chlorobiphenyl + 3,4-dihydro-3,4-dihydroxy-2,2'-dichlorobiphenyl + NAD+
-
-
-
?
2,2'-dichlorobiphenyl + NADH + H+ + O2
2,3-dihydroxy-2'-chlorobiphenyl + 3,4-dihydro-3,4-dihydroxy-2,2'-dichlorobiphenyl + NAD+
-
-
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

?
-
-
-
?
2,2'-dichlorobiphenyl + NADH + H+ + O2
?
-
-
-
?
2,2'-dichlorobiphenyl + NADH + H+ + O2
?
-
wild-type enzyme
-
?
2,2'-dichlorobiphenyl + NADH + H+ + O2
?
-
-
-
?
2,2'-dichlorobiphenyl + NADH + H+ + O2
?
-
-
-
?
2,2'-dichlorobiphenyl + NADH + H+ + O2
?
-
-
-
?
2,2'-dichlorobiphenyl + NADH + H+ + O2
?
-
-
-
?
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
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 + NAD+ + HCl
-
-
-
?
2,2'-dichlorobiphenyl + NADH + O2
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
-
-
-
?
2,2'-dichlorobiphenyl + NADH + O2
5,6-dihydroxy-1-phenylcyclohexa-1,3-diene + 2,3-dihydroxy-2'-chlorobiphenyl + NAD+ + HCl
-
-
-
?
2,2'-difluorobiphenyl + NADH + H+ + O2

?
-
-
-
?
2,2'-difluorobiphenyl + NADH + H+ + O2
?
-
-
-
?
2,2'-difluorobiphenyl + NADH + O2

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
-
-
-
?
2,2'-dihydroxybiphenyl + NADH + H+ + O2

?
-
-
-
?
2,2'-dihydroxybiphenyl + NADH + H+ + O2
?
-
-
-
?
2,2'-dihydroxybiphenyl + NADH + O2

2,3,2'-trihydroxybiphenyl + trihydroxybiphenyl + NAD+
-
-
-
?
2,2'-dihydroxybiphenyl + NADH + O2
2,3,2'-trihydroxybiphenyl + trihydroxybiphenyl + NAD+
-
-
-
?
2,2'-dinitrobiphenyl + NADH + O2

2,3-dihydroxy-2'-nitrobiphenyl + NAD+ + NO2
-
-
-
?
2,2'-dinitrobiphenyl + NADH + O2
2,3-dihydroxy-2'-nitrobiphenyl + NAD+ + NO2
-
-
-
?
2,3',4-trichlorobiphenyl + NADH + H+ + O2

?
-
-
-
?
2,3',4-trichlorobiphenyl + NADH + H+ + O2
?
-
-
-
?
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 + 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
-
-
-
?
2,3,4'-trichlorobiphenyl + NADH + H+ + O2

?
-
-
-
?
2,3,4'-trichlorobiphenyl + NADH + H+ + O2
?
-
-
-
?
2,4'-dichlorobiphenyl + NADH + O2

2,3-dihydroxy-4'-chlorobiphenyl + NAD+ + HCl
-
-
-
?
2,4'-dichlorobiphenyl + NADH + O2
2,3-dihydroxy-4'-chlorobiphenyl + NAD+ + HCl
-
-
-
?
2,4,4'-trichlorobiphenyl + NADH + H+ + O2

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+
-
-
-
?
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',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
-
-
-
?
2,5,4'-trichlorobiphenyl + NADH + O2

?
-
-
-
?
2,5,4'-trichlorobiphenyl + NADH + O2
?
-
-
-
?
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
-
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-dichlorobiphenyl + NADH + H+ + O2

2,6-dichloro-2',3'-dihydro-2',3'-dihydroxybiphenyl + ?
-
-
-
?
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-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
-
?
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
-
?
2-hydroxy-3,5-dichlorobiphenyl + NADH + H+ + O2
?
-
ortho-meta-oxygenation, hydroxylation on the non-substituted ring
-
?
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
?
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-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
?
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
?
3,3'-dichlorobiphenyl + NADH + H+ + O2

?
-
wild-type enzyme
-
?
3,3'-dichlorobiphenyl + NADH + H+ + O2
?
-
-
-
?
3,3'-dichlorobiphenyl + NADH + H+ + O2
?
-
-
-
?
3,3'-dichlorobiphenyl + NADH + H+ + O2
?
-
-
-
?
3,3'-dichlorobiphenyl + NADH + H+ + O2
?
-
-
-
?
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
-
-
-
?
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
-
-
-
?
3,4'-dichlorobiphenyl + NAD(P)H + O2

5,6-dihydroxy-3,4'-dichlorobiphenyl + NAD(P)+
-
-
-
?
3,4'-dichlorobiphenyl + NAD(P)H + O2
5,6-dihydroxy-3,4'-dichlorobiphenyl + NAD(P)+
-
-
-
?
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'-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+
-
-
-
?
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+
-
-
-
?
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)+
-
-
-
?
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)+
-
-
-
?
4,4'-dichlorobiphenyl + NADH + H+ + O2

?
-
-
-
?
4,4'-dichlorobiphenyl + NADH + H+ + O2
?
-
-
-
?
4,4'-dichlorobiphenyl + NADH + H+ + O2
?
-
-
-
?
4,4'-dichlorobiphenyl + NADH + H+ + O2
?
-
-
-
?
4,4'-dichlorobiphenyl + NADH + H+ + O2
?
-
-
-
?
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+
-
-
-
?
4-chlorobiphenyl + NADH + O2
2',3'-dihydrodiol-4-chlorobiphenyl + NAD+
-
-
-
?
4-methylbiphenyl + NADH + O2

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+
-
-
-
?
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
-
?
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
-
?
6,7-dihydro-5H-benzocycloheptene + NAD(P)H + O2

(-)-cis-(1R,2S)-dihydroxybenzocycloheptane + NAD(P)+
-
-
-
?
6,7-dihydro-5H-benzocycloheptene + NAD(P)H + O2
(-)-cis-(1R,2S)-dihydroxybenzocycloheptane + NAD(P)+
-
-
-
?
6-hydroxyflavanone + O2 + NAD(P)H

?
-
-
-
?
6-hydroxyflavanone + O2 + NAD(P)H
?
-
-
-
?
7-hydroxyflavanone + O2 + NAD(P)H

?
-
-
-
?
7-hydroxyflavanone + O2 + NAD(P)H
?
-
-
-
?
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
-
?
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
-
?
benzo[a]pyrene + NADH + O2

?
-
-
-
?
benzo[a]pyrene + NADH + O2
?
-
-
-
?
biphenyl + NAD(P)H + O2

(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)+
-
-
-
?
biphenyl + NAD(P)H + O2
2,3-dihydro-dihydroxybiphenyl + 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)+
-
-
-
?
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)+
-
-
-
?
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+
-
-
-
?
biphenyl + NADH + H+ + O2
(1S,2R)-3-phenylcyclohexa-3,5-diene-1,2-diol + 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+
-
-
-
?
biphenyl + NADH + H+ + O2
2,3-dihydro-dihydroxybiphenyl + NAD+
-
-
-
?
biphenyl + NADH + H+ + O2

?
-
-
-
?
biphenyl + NADH + H+ + O2
?
-
wild-type enzyme
-
?
biphenyl + NADH + O2

cis-biphenyl 2,3-dihydrodiol + NAD+
-
-
-
?
biphenyl + NADH + O2
cis-biphenyl 2,3-dihydrodiol + NAD+
-
-
-
?
carbazole + NADH + O2

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
-
?
dibenzo-p-dioxin + NADH + O2

2,2',3-trihydroxybiphenyl ether + NAD+
-
-
-
?
dibenzo-p-dioxin + NADH + O2
2,2',3-trihydroxybiphenyl ether + NAD+
-
-
-
?
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
?
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
?
flavone + O2 + NADH + H+

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 + ?
-
the flavone metabolite is 2-[(5S,6R)-5,6-dihydroxycyclohexa-1,3-dienyl]-4H-chromen-4-one
-
?
isoflavone + O2 + NADH + H+

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+
-
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
-
?
naphthalene + NADH + O2

?
-
-
-
?
naphthalene + NADH + O2
?
-
-
-
?
naphthalene + NADPH + O2

cis-naphthalene 1,2-dihydrodiol + NADP+
-
poor substrate
-
?
naphthalene + NADPH + O2
cis-naphthalene 1,2-dihydrodiol + NADP+
-
poor substrate
-
?
phenanthrene + NADH + O2

?
-
-
-
?
phenanthrene + NADH + O2
?
-
-
-
?
phenazine + NADH + H+ + O2

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 3,3'-dichlorobiphenyl
-
?
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
?
-
-
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
?
-
-
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
?
-
-
overview on polychlorinated biphenyls
-
?
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
-
?
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Resnick, S.M.; Torok, D.S.; Gibson, D.T.
Oxidation of carbazole to 3-hydroxycarbazole by naphthalene 1,2-dioxygenase and biphenyl 2,3-dioxygenase
FEMS Microbiol. Lett.
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297-302
1993
Sphingobium yanoikuyae, Sphingobium yanoikuyae B8/36
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Erickson, B.D.; Mondello, F.J.
Enhanced biodegradation of polychlorated biphenyls after site-directed mutagenesis of a biphenyl dioxygenase gene
Appl. Environ. Microbiol.
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Pseudomonas sp., Pseudomonas oleovorans, Pseudomonas sp. LB400, Pseudomonas oleovorans KF707
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Haddock, J.D.; Horton, J.R.; Gibson, D.T.
Dihydroxylation and dechlorination of chlorinated biphenyls by purified biphenyl 2,3-dioxygenase from Pseudomonas sp. strain LB400
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Pseudomonas sp., Pseudomonas sp. LB400
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Seeger, M.; Timmis, K.N.; Hofer, B.
Degradation of chlorobiphenyls catalyzed by the bph-encoded biphenyl-2,3-dioxygenase and biphenyl-2,3-dihydrodiol-2,3-dehydrogenase of Pseudomonas sp. LB400
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1995
Pseudomonas sp., Pseudomonas sp. LB400
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Haddock, J.D.; Gibson, D.T.
Purification and characterization of the oxygenase component of biphenyl 2,3-dioxygenase from Pseudomonas sp. strain LB400
J. Bacteriol.
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5834-5839
1995
Pseudomonas sp., Pseudomonas sp. LB400
brenda
Hurtubise, Y.; Barriault, D.; Sylvestre, M.
Characterization of active recombinant His-tagged oxygenase component of Comamonas testosteroni B-356 biphenyl dioxygenase
J. Biol. Chem.
271
8152-8156
1996
Comamonas testosteroni
brenda
Resnick, S.M.; Gibson, D.T.
Oxidation of 6,7-dihydro-5H-benzocycloheptene by bacterial strains expressing naphthalene dioxygenase, biphenyl dioxygenase, and toluene dioxygenase yields homochiral mono-ol or cis-diol enantiomers as major products
Appl. Environ. Microbiol.
62
1364-1368
1996
Sphingobium yanoikuyae, Sphingobium yanoikuyae B8/36
brenda
McKay, D.B.; Seeger, M.; Zielinski, M.; Hofer, B.; Timmis, K.N.
Heterologous expression of biphenyl dioxygenase-encoding genes from a gram-positive broad-spectrum polychlorinated biphenyl degrader and characterization of chlorobiphenyl oxidation by the gene products
J. Bacteriol.
179
1924-1930
1997
Rhodococcus globerulus, Rhodococcus globerulus P6
brenda
Broadus, R.M.; Haddock, J.D.
Purification and characterization of the NADH:ferredoxinBPH oxidoreductase component of biphenyl 2,3-dioxygenase from Pseudomonas sp. strain LB400
Arch. Microbiol.
170
106-112
1998
Pseudomonas sp., Pseudomonas sp. LB400
brenda
Hurtubise, Y.; Barriault, D.; Sylvestre, M.
Involvement of the terminal oxygenase beta subunit in the biphenyl dioxygenase reactivity pattern toward chlorobiphenyls
J. Bacteriol.
180
5828-5835
1998
Comamonas testosteroni, Pseudomonas sp., Pseudomonas sp. LB400
brenda
Chebrou, H.; Hurtubise, Y.; Barriault, D.; Sylvestre, M.
Heterologous expression and characterization of the purified oxygenase component of Rhodococcus globerulus P6 biphenyl dioxygenase and of chimeras derived from it
J. Bacteriol.
181
4805-4811
1999
Rhodococcus globerulus, Rhodococcus globerulus P6
brenda
Arnett, C.M.; Parales, J.V.; Haddock, J.D.
Influence of chlorine substituents on rates of oxidation of chlorinated biphenyls by the biphenyl dioxygenase of Burkholderia sp. strain LB400
Appl. Environ. Microbiol.
66
2928-2933
2000
Pseudomonas sp., Pseudomonas sp. LB400
brenda
Seeger, M.; Camara, B.; Hofer, B.
Dehalogenation, denitration, dehydroxylation, and angular attack on substituted biphenyls and related compounds by a biphenyl dioxygenase
J. Bacteriol.
183
3548-3555
2001
Burkholderia sp., Pseudomonas sp., Pseudomonas sp. LB400, Burkholderia sp. LB400
brenda
Imbeault, N.Y.; Powlowski, J.B.; Colbert, C.L.; Bolin, J.T.; Eltis, L.D.
Steady-state kinetic characterization and crystallization of a polychlorinated biphenyl-transforming dioxygenase
J. Biol. Chem.
275
12430-12437
2000
Comamonas testosteroni
brenda
Kim, S.Y.; Jung, J.; Lim, Y.; Ahn, J.H.; Kim, S.I.; Hur, H.G.
cis-2', 3'-Dihydrodiol production on flavone B-ring by biphenyl dioxygenase from Pseudomonas pseudoalcaligenes KF707 expressed in Escherichia coli
Antonie van Leeuwenhoek
84
261-268
2003
Pseudomonas oleovorans, Pseudomonas oleovorans KF707
brenda
L'Abbee J.B.; Barriault, D.; Sylvestre, M.
Metabolism of dibenzofuran and dibenzo-p-dioxin by the biphenyl dioxygenase of Burkholderia xenovorans LB400 and Comamonas testosteroni B-356
Appl. Microbiol. Biotechnol.
67
506-514
2005
Comamonas testosteroni, Paraburkholderia xenovorans
brenda
Barriault, D.; Simard, C.; Chatel, H.; Sylvestre, M.
Characterization of hybrid biphenyl dioxygenases obtained by recombining Burkholderia sp. strain LB400 bphA with the homologous gene of Comamonas testosteroni B-356
Can. J. Microbiol.
47
1025-1032
2001
Burkholderia sp., Comamonas testosteroni
brenda
Francova, K.; Mackova, M.; Macek, T.; Sylvestre, M.
Ability of bacterial biphenyl dioxygenases from Burkholderia sp. LB400 and Comamonas testosteroni B-356 to catalyse oxygenation of ortho-hydroxychlorobiphenyls formed from PCBs by plants
Environ. Pollut.
127
41-48
2004
Burkholderia sp., Comamonas testosteroni, Burkholderia sp. LB400
brenda
Suenaga, H.; Mitsuoka, M.; Ura, Y.; Watanabe, T.; Furukawa, K.
Directed evolution of biphenyl dioxygenase: emergence of enhanced degradation capacity for benzene, toluene, and alkylbenzenes
J. Bacteriol.
183
5441-5444
2001
Pseudomonas oleovorans, Pseudomonas oleovorans KF707
brenda
Barriault, D.; Plante, M.M.; Sylvestre, M.
Family shuffling of a targeted bphA region to engineer biphenyl dioxygenase
J. Bacteriol.
184
3794-3800
2002
Burkholderia sp., Comamonas testosteroni, Burkholderia sp. LB4000
brenda
Zielinski, M.; Kahl, S.; Hecht, H.J.; Hofer, B.
Pinpointing biphenyl dioxygenase residues that are crucial for substrate interaction
J. Bacteriol.
185
6976-6980
2003
Burkholderia sp., Burkholderia sp. LB400
brenda
Barriault, D.; Sylvestre, M.
Evolution of the biphenyl dioxygenase BphA from Burkholderia xenovorans LB400 by random mutagenesis of multiple sites in region III
J. Biol. Chem.
279
47480-47488
2004
Paraburkholderia xenovorans
brenda
Barriault, D.; Lepine, F.; Mohammadi, M.; Milot, S.; Leberre, N.; Sylvestre, M.
Revisiting the regiospecificity of Burkholderia xenovorans LB400 biphenyl dioxygenase toward 2,2'-dichlorobiphenyl and 2,3,2',3'-tetrachlorobiphenyl
J. Biol. Chem.
279
47489-47496
2004
Paraburkholderia xenovorans
brenda
Furusawa, Y.; Nagarajan, V.; Tanokura, M.; Masai, E.; Fukuda, M.; Senda, T.
Crystal structure of the terminal oxygenase component of biphenyl dioxygenase derived from Rhodococcus sp. strain RHA1
J. Mol. Biol.
342
1041-1052
2004
Rhodococcus sp. (Q53122), Rhodococcus sp. RHA1 (Q53122)
brenda
Zielinski, M.; Backhaus, S.; Hofer, B.
The principal determinants for the structure of the substrate-binding pocket are located within a central core of a biphenyl dioxygenase alpha subunit
Microbiology
148
2439-2448
2002
Burkholderia sp., Rhodococcus globerulus, Rhodococcus globerulus P6, Burkhol