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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

Reaction

biphenyl
+
NADH
+
H+
+
O2
=
(1S,2R)-3-phenylcyclohexa-3,5-diene-1,2-diol
+
NAD+

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

     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

Substrates Products

Substrates Products on EC 1.14.12.18 - biphenyl 2,3-dioxygenase

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SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
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+
show the reaction diagram
(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+
show the reaction diagram
(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+
show the reaction diagram
(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+
show the reaction diagram
-
-
-
-
?
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+
show the reaction diagram
-
-
-
-
?
2,2',3,3'-tetrachlorobiphenyl + NADH + H+ + O2
?
show the reaction diagram
2,2',3,3'-tetrachlorobiphenyl + NADH + O2
?
show the reaction diagram
2,2',5,5'-tetrachlorobiphenyl + NADH + H+ + O2
3,4-dihydro-3,4-dihydroxy-2,2',5,5'-tetrachlorobiphenyl + NAD+
show the reaction diagram
-
-
-
-
?
2,2',5,5'-tetrachlorobiphenyl + NADH + H+ + O2
?
show the reaction diagram
2,2',5,5'-tetrachlorobiphenyl + NADH + O2
?
show the reaction diagram
2,2'-dibromobiphenyl + NADH + H+ + O2
?
show the reaction diagram
2,2'-dibromobiphenyl + NADH + O2
2,3-dihydroxy-2'-bromobiphenyl + NAD+ + HBr
show the reaction diagram
2,2'-dichlorobiphenyl + NADH + H+ + O2
2,3-dihydroxy-2'-chlorobiphenyl + 3,4-dihydro-3,4-dihydroxy-2,2'-dichlorobiphenyl + NAD+ + HCl
show the reaction diagram
2,2'-dichlorobiphenyl + NADH + H+ + O2
2,3-dihydroxy-2'-chlorobiphenyl + cis-3,4-dihydro-3,4-dihydroxy-2,2'-dichlorobiphenyl + NAD+ + HCl
show the reaction diagram
-
-
-
-
?
2,2'-dichlorobiphenyl + NADH + H+ + O2
2,3-dihydroxy-2'-chlorobiphenyl + NAD+ + HCl
show the reaction diagram
-
poor substrate
-
-
?
2,2'-dichlorobiphenyl + NADH + H+ + O2
?
show the reaction diagram
2,2'-dichlorobiphenyl + NADH + O2
2,3-dihydroxy-2'-chlorobiphenyl + 3,4-dihydro-3,4-dihydroxy-2,2'-dichlorobiphenyl + NAD+
show the reaction diagram
2,2'-dichlorobiphenyl + NADH + O2
2,3-dihydroxy-2'-chlorobiphenyl + NAD+ + HCl
show the reaction diagram
2,2'-dichlorobiphenyl + NADH + O2
5,6-dihydroxy-1-phenylcyclohexa-1,3-diene + 2,3-dihydroxy-2'-chlorobiphenyl + NAD+ + HCl
show the reaction diagram
2,2'-difluorobiphenyl + NADH + H+ + O2
?
show the reaction diagram
2,2'-difluorobiphenyl + NADH + O2
2,3-dihydroxy-2'-fluorobiphenyl + 5,6-dihydroxy-2,2'-difluorobiphenyl + NAD+ + HF
show the reaction diagram
2,2'-dihydroxybiphenyl + NADH + H+ + O2
?
show the reaction diagram
2,2'-dihydroxybiphenyl + NADH + O2
2,3,2'-trihydroxybiphenyl + trihydroxybiphenyl + NAD+
show the reaction diagram
2,2'-dinitrobiphenyl + NADH + H+ + O2
?
show the reaction diagram
-
-
-
-
?
2,2'-dinitrobiphenyl + NADH + O2
2,3-dihydroxy-2'-nitrobiphenyl + NAD+ + NO2
show the reaction diagram
2,3',4'-trichlorobiphenyl + NADH + O2
?
show the reaction diagram
-
-
-
-
?
2,3',4-trichlorobiphenyl + NADH + H+ + O2
?
show the reaction diagram
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
show the reaction diagram
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
show the reaction diagram
-
-
-
-
?
2,3,2',3'-tetrachlorobiphenyl + NADH + H+ + O2
4,5-dihydro-4,5-dihydroxy-2,3,2',3'-tetrachlorobiphenyl + NAD+
show the reaction diagram
-
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+
show the reaction diagram
-
-
-
-
?
2,3,4'-trichlorobiphenyl + NADH + H+ + O2
?
show the reaction diagram
2,3,4'-trichlorobiphenyl + NADH + O2
?
show the reaction diagram
-
-
-
-
?
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+
show the reaction diagram
-
-
-
-
?
2,4'-dichlorobiphenyl + NADH + O2
2,3-dihydroxy-4'-chlorobiphenyl + NAD+ + HCl
show the reaction diagram
2,4,2',4'-tetrachlorobiphenyl + NADH + H+ + O2
2,3-dihydroxy-2',4,4'-trichlorobiphenyl + NAD+ + HCl
show the reaction diagram
-
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+
show the reaction diagram
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
show the reaction diagram
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
show the reaction diagram
-
-
-
-
?
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
show the reaction diagram
-
-
-
-
?
2,5,4'-trichlorobiphenyl + NADH + O2
?
show the reaction diagram
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
show the reaction diagram
2,6',4'-trichlorobiphenyl + NADH + O2
?
show the reaction diagram
-
-
-
-
?
2,6-dichlorobiphenyl + NADH + H+ + O2
2,6-dichloro-2',3'-dihydro-2',3'-dihydroxybiphenyl + ?
show the reaction diagram
2,6-dichlorobiphenyl + NADH + H+ + O2
?
show the reaction diagram
-
poor substrate
-
-
?
2-chlorobiphenyl + NADH + O2
cis-2',3'-dihydroxy-1'-(2-chlorophenyl)-cyclohexa-4',6'-diene + catechol + NAD+
show the reaction diagram
2-hydroxy-3,5-dichlorobiphenyl + NADH + H+ + O2
?
show the reaction diagram
2-hydroxy-3-chlorobiphenyl + NADH + H+ + O2
5-(3-chloro-2-hydroxyphenyl)-6-hydroxy-3-cyclohexen-1-one + NAD+
show the reaction diagram
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+
show the reaction diagram
3,3'-dichlorobiphenyl + NADH + H+ + O2
5,6-dihydroxy-1-phenylcyclohexa-1,3-diene + 4,5-dihydroxy-1-phenylcyclohexa-1,2-diene + NAD+ + HCl
show the reaction diagram
-
-
-
?
3,3'-dichlorobiphenyl + NADH + H+ + O2
?
show the reaction diagram
3,3'-dichlorobiphenyl + NADH + O2
5,6-dihydroxy-1-phenylcyclohexa-1,3-diene + 4,5-dihydroxy-1-phenylcyclohexa-1,2-diene + NAD+ + HCl
show the reaction diagram
3,3'-dichlorobiphenyl + NADH + O2
?
show the reaction diagram
-
-
-
-
?
3,4'-dichlorobiphenyl + NAD(P)H + O2
5,6-dihydroxy-3,4'-dichlorobiphenyl + NAD(P)+
show the reaction diagram
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
show the reaction diagram
3,4,4'-trichlorobiphenyl + NADH + O2
?
show the reaction diagram
-
-
-
-
?
3,5',4'-trichlorobiphenyl + NADH + O2
?
show the reaction diagram
-
-
-
-
?
3-chlorobiphenyl + NADH + O2
cis-2',3'-dihydroxy-1'-(3-chlorophenyl)-cyclohexa-4',6'-diene + NAD+
show the reaction diagram
4,4'-dichlorobiphenyl + NAD(P)H + O2
2,3-dihydroxy-4,4'-dichlorobiphenyl + NAD(P)+
show the reaction diagram
4,4'-dichlorobiphenyl + NADH + H+ + O2
2,3-dihydroxy-4,4'-dichlorobiphenyl + NAD+
show the reaction diagram
-
-
-
?
4,4'-dichlorobiphenyl + NADH + H+ + O2
?
show the reaction diagram
4-chlorobiphenyl + NADH + O2
2',3'-dihydrodiol-4-chlorobiphenyl + NAD+
show the reaction diagram
4-methylbiphenyl + NADH + O2
2-hydroxy-6-oxo-6-[4-methylphenyl]-hexa-2,4-dienoic acid + NAD+
show the reaction diagram
5,7-dihydroxyflavone + NADH + H+ + O2
2-(2,3-dihydroxyphenyl)-5,7-dihydroxy-chromen-4-one + NAD+
show the reaction diagram
6,7-dihydro-5H-benzocycloheptene + NAD(P)H + O2
(-)-cis-(1R,2S)-dihydroxybenzocycloheptane + NAD(P)+
show the reaction diagram
6-hydroxyflavanone + O2 + NAD(P)H
?
show the reaction diagram
7-hydroxyflavanone + O2 + NAD(P)H
?
show the reaction diagram
7-hydroxyflavone + NADH + H+ + O2
2-(2,3-dihydroxyphenyl)-7-hydroxy-chromen-4-one + NAD+
show the reaction diagram
benzene + ?
?
show the reaction diagram
-
benzene is only a substrate for Pseudomonas pseudoalcaligenes strain 1072
-
-
?
benzo[a]pyrene + NADH + O2
?
show the reaction diagram
biphenyl + NAD(P)H + O2
(1S,2R)-dihydroxy-3-phenylcyclohexa-3,5-diene + NAD(P)+
show the reaction diagram
biphenyl + NAD(P)H + O2
2,3-dihydro-dihydroxybiphenyl + NAD(P)+
show the reaction diagram
biphenyl + NAD(P)H + O2
cis-biphenyl 2,3-dihydrodiol + NAD(P)+
show the reaction diagram
biphenyl + NADH + H+ + O2
(1S,2R)-3-phenylcyclohexa-3,5-diene-1,2-diol + NAD+
show the reaction diagram
biphenyl + NADH + H+ + O2
(1S,2R)-3-phenylcyclohexa-3,5-diene-1,2-diol + NAD+ + ?
show the reaction diagram
-
-
-
-
?
biphenyl + NADH + H+ + O2
2,3-dihydro-dihydroxybiphenyl + NAD+
show the reaction diagram
biphenyl + NADH + H+ + O2
?
show the reaction diagram
biphenyl + NADH + H+ + O2
cis-(2R,3S)-dihydroxy-1-phenylcyclohexa-4,6-diene + NAD+
show the reaction diagram
-
-
-
-
?
biphenyl + NADH + O2
cis-biphenyl 2,3-dihydrodiol + NAD+
show the reaction diagram
carbazole + NADH + O2
3-hydroxycarbazole + NAD+
show the reaction diagram
dibenzo-p-dioxin + NADH + O2
2,2',3-trihydroxybiphenyl ether + NAD+
show the reaction diagram
dibenzo-p-dioxine + NADH + O2
2,3,2'-trihydroxy-diphenylether + dibenzo-p-dioxine-dihydrodiol + NAD+
show the reaction diagram
-
-
-
-
?
dibenzofuran + NADH + O2
?
show the reaction diagram
-
dibenzofuran is a poor substrate
-
-
?
dibenzofurane + NADH + O2
2,2',3-trihydroxybiphenyl + dihydro-dihydroxy-dibenzofuran + NAD+
show the reaction diagram
dibenzofurane + NADH + O2
monohydroxydibenzofuran + 2,3,2'-trihydroxybiphenyl + dibenzofuran-1,2-dihydrodiol + dibenzofuran-3,4-dihydrodiol + NAD+
show the reaction diagram
-
-
-
-
?
diphenylmethane + NADH + O2
?
show the reaction diagram
-
-
-
-
?
ethylbenzene + ?
?
show the reaction diagram
-
-
-
-
?
ethylbenzene + NADH + O2
?
show the reaction diagram
-
-
-
-
?
flavone + O2 + NAD(P)H
cis-flavone-2',3'-dihydrodiol + ?
show the reaction diagram
-
-
-
-
?
flavone + O2 + NADH + H+
cis-flavone-2',3'-dihydrodiol + ?
show the reaction diagram
isoflavone + NADH + H+ + O2
isoflavone-cis-(2'R,3'S)-dihydrodiol + NAD+
show the reaction diagram
-
-
-
-
?
isoflavone + O2 + NADH + H+
2',3'-dihydro-2',3'-cis-dihydroxyflavone + NAD+
show the reaction diagram
naphthalene + NADH + O2
?
show the reaction diagram
naphthalene + NADPH + O2
cis-naphthalene 1,2-dihydrodiol + NADP+
show the reaction diagram
phenanthrene + NADH + O2
?
show the reaction diagram
phenazine + NADH + H+ + O2
1,2-dihydro-1,2-dihydroxyphenazine + NAD+
show the reaction diagram
toluene + NAD(P)H + O2
?
show the reaction diagram
-
toluene is only a substrate for Pseudomonas pseudoalcaligenes strain 1072
-
-
?
additional information
?
-