1.14.12.18 (3R,4R)-cis-isoflavan-4-ol + NADH + H+ + O2 - Pseudomonas oleovorans (3R,4R)-3-(7-oxabicyclo[4.1.0]hepta-1,3,5-trien-2-yl)-3,4-dihydro-2H-chromen-4-ol + NAD+ - ? 413709 1.14.12.18 (3R,4R)-cis-isoflavan-4-ol + NADH + H+ + O2 - Pseudomonas oleovorans KF707 (3R,4R)-3-(7-oxabicyclo[4.1.0]hepta-1,3,5-trien-2-yl)-3,4-dihydro-2H-chromen-4-ol + NAD+ - ? 413709 1.14.12.18 (3R,4S)-trans-isoflavan-4-ol + NADH + H+ + O2 - Pseudomonas oleovorans (3R,4S)-3-(7-oxabicyclo[4.1.0]hepta-1,3,5-trien-2-yl)-3,4-dihydro-2H-chromen-4-ol + NAD+ - ? 413710 1.14.12.18 (3R,4S)-trans-isoflavan-4-ol + NADH + H+ + O2 - 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+ - ? 413710 1.14.12.18 (3S,4R)-trans-isoflavan-4-ol + NADH + H+ + O2 - Pseudomonas oleovorans (3S,4R)-3-(7-oxabicyclo[4.1.0]hepta-1,3,5-trien-2-yl)-3,4-dihydro-2H-chromen-4-ol + NAD+ - ? 413711 1.14.12.18 (3S,4R)-trans-isoflavan-4-ol + NADH + H+ + O2 - 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+ - ? 413711 1.14.12.18 (3S,4S)-cis-isoflavan-4-ol + NADH + H+ + O2 - Pseudomonas oleovorans (3S,4S)-3-(7-oxabicyclo[4.1.0]hepta-1,3,5-trien-2-yl)-3,4-dihydro-2H-chromen-4-ol + NAD+ - ? 413712 1.14.12.18 2,2',3,3'-tetrachlorobiphenyl + NADH + H+ + O2 - Paraburkholderia xenovorans 5,6-dihydro-5,6-dihydroxy-2,2',3,3'-tetrachlorobiphenyl + 4,5-dihydro-4,5-dihydroxy-2,2',3,3'-tetrachlorobiphenyl + NAD+ - ? 387068 1.14.12.18 2,2',3,3'-tetrachlorobiphenyl + NADH + H+ + O2 - Paraburkholderia xenovorans ? - ? 395335 1.14.12.18 2,2',3,3'-tetrachlorobiphenyl + NADH + H+ + O2 - Pandoraea pnomenusa ? - ? 395335 1.14.12.18 2,2',3,3'-tetrachlorobiphenyl + NADH + H+ + O2 - Pandoraea pnomenusa B-356 ? - ? 395335 1.14.12.18 2,2',3,3'-tetrachlorobiphenyl + NADH + O2 - Comamonas testosteroni ? - ? 375600 1.14.12.18 2,2',3,3'-tetrachlorobiphenyl + NADH + O2 - Burkholderia sp. ? - ? 375600 1.14.12.18 2,2',3,3'-tetrachlorobiphenyl + NADH + O2 - Burkholderia sp. LB4000 ? - ? 375600 1.14.12.18 2,2',5,5'-tetrachlorobiphenyl + NADH + H+ + O2 - Burkholderia sp. ? - ? 375601 1.14.12.18 2,2',5,5'-tetrachlorobiphenyl + NADH + H+ + O2 - Paraburkholderia xenovorans ? - ? 375601 1.14.12.18 2,2',5,5'-tetrachlorobiphenyl + NADH + H+ + O2 - Pandoraea pnomenusa ? - ? 375601 1.14.12.18 2,2',5,5'-tetrachlorobiphenyl + NADH + H+ + O2 - Pandoraea pnomenusa B-356 ? - ? 375601 1.14.12.18 2,2',5,5'-tetrachlorobiphenyl + NADH + H+ + O2 - Paraburkholderia xenovorans 3,4-dihydro-3,4-dihydroxy-2,2',5,5'-tetrachlorobiphenyl + NAD+ - ? 387071 1.14.12.18 2,2',5,5'-tetrachlorobiphenyl + NADH + O2 - Burkholderia sp. ? - ? 375602 1.14.12.18 2,2',5,5'-tetrachlorobiphenyl + NADH + O2 - Burkholderia sp. LB4000 ? - ? 375602 1.14.12.18 2,2'-dibromobiphenyl + NADH + H+ + O2 - Burkholderia sp. ? - ? 375605 1.14.12.18 2,2'-dibromobiphenyl + NADH + H+ + O2 - Burkholderia sp. LB400 ? - ? 375605 1.14.12.18 2,2'-dibromobiphenyl + NADH + O2 - Pseudomonas sp. 2,3-dihydroxy-2'-bromobiphenyl + NAD+ + HBr - ? 186699 1.14.12.18 2,2'-dibromobiphenyl + NADH + O2 - Pseudomonas sp. LB400 2,3-dihydroxy-2'-bromobiphenyl + NAD+ + HBr - ? 186699 1.14.12.18 2,2'-dichlorobiphenyl + NADH + H+ + O2 - Paraburkholderia xenovorans 2,3-dihydroxy-2'-chlorobiphenyl + 3,4-dihydro-3,4-dihydroxy-2,2'-dichlorobiphenyl + NAD+ + HCl - ? 375606 1.14.12.18 2,2'-dichlorobiphenyl + NADH + H+ + O2 - Paraburkholderia xenovorans 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 ? 375606 1.14.12.18 2,2'-dichlorobiphenyl + NADH + H+ + O2 - Paraburkholderia xenovorans 2,3-dihydroxy-2'-chlorobiphenyl + cis-3,4-dihydro-3,4-dihydroxy-2,2'-dichlorobiphenyl + NAD+ + HCl - ? 375607 1.14.12.18 2,2'-dichlorobiphenyl + NADH + H+ + O2 - Pseudomonas sp. ? - ? 375608 1.14.12.18 2,2'-dichlorobiphenyl + NADH + H+ + O2 - Burkholderia sp. ? - ? 375608 1.14.12.18 2,2'-dichlorobiphenyl + NADH + H+ + O2 - Paraburkholderia xenovorans ? - ? 375608 1.14.12.18 2,2'-dichlorobiphenyl + NADH + H+ + O2 - Pandoraea pnomenusa ? - ? 375608 1.14.12.18 2,2'-dichlorobiphenyl + NADH + H+ + O2 wild-type enzyme Comamonas testosteroni ? - ? 375608 1.14.12.18 2,2'-dichlorobiphenyl + NADH + H+ + O2 - Pandoraea pnomenusa B-356 ? - ? 375608 1.14.12.18 2,2'-dichlorobiphenyl + NADH + H+ + O2 - Burkholderia sp. LB400 ? - ? 375608 1.14.12.18 2,2'-dichlorobiphenyl + NADH + H+ + O2 poor substrate Paraburkholderia xenovorans 2,3-dihydroxy-2'-chlorobiphenyl + NAD+ + HCl - ? 413889 1.14.12.18 2,2'-dichlorobiphenyl + NADH + O2 - Pseudomonas sp. 5,6-dihydroxy-1-phenylcyclohexa-1,3-diene + 2,3-dihydroxy-2'-chlorobiphenyl + NAD+ + HCl - ? 186685 1.14.12.18 2,2'-dichlorobiphenyl + NADH + O2 - Comamonas testosteroni 5,6-dihydroxy-1-phenylcyclohexa-1,3-diene + 2,3-dihydroxy-2'-chlorobiphenyl + NAD+ + HCl - ? 186685 1.14.12.18 2,2'-dichlorobiphenyl + NADH + O2 - Rhodococcus globerulus 5,6-dihydroxy-1-phenylcyclohexa-1,3-diene + 2,3-dihydroxy-2'-chlorobiphenyl + NAD+ + HCl - ? 186685 1.14.12.18 2,2'-dichlorobiphenyl + NADH + O2 - Rhodococcus globerulus P6 5,6-dihydroxy-1-phenylcyclohexa-1,3-diene + 2,3-dihydroxy-2'-chlorobiphenyl + NAD+ + HCl - ? 186685 1.14.12.18 2,2'-dichlorobiphenyl + NADH + O2 - Pseudomonas sp. LB400 5,6-dihydroxy-1-phenylcyclohexa-1,3-diene + 2,3-dihydroxy-2'-chlorobiphenyl + NAD+ + HCl - ? 186685 1.14.12.18 2,2'-dichlorobiphenyl + NADH + O2 - Pseudomonas sp. 2,3-dihydroxy-2'-chlorobiphenyl + NAD+ + HCl - ? 186698 1.14.12.18 2,2'-dichlorobiphenyl + NADH + O2 - Pseudomonas sp. LB400 2,3-dihydroxy-2'-chlorobiphenyl + NAD+ + HCl - ? 186698 1.14.12.18 2,2'-dichlorobiphenyl + NADH + O2 - Pseudomonas oleovorans 2,3-dihydroxy-2'-chlorobiphenyl + 3,4-dihydro-3,4-dihydroxy-2,2'-dichlorobiphenyl + NAD+ - ? 387073 1.14.12.18 2,2'-dichlorobiphenyl + NADH + O2 - Pseudomonas oleovorans KF707 2,3-dihydroxy-2'-chlorobiphenyl + 3,4-dihydro-3,4-dihydroxy-2,2'-dichlorobiphenyl + NAD+ - ? 387073 1.14.12.18 2,2'-difluorobiphenyl + NADH + H+ + O2 - Burkholderia sp. ? - ? 375609 1.14.12.18 2,2'-difluorobiphenyl + NADH + H+ + O2 - Burkholderia sp. LB400 ? - ? 375609 1.14.12.18 2,2'-difluorobiphenyl + NADH + O2 - Pseudomonas sp. 2,3-dihydroxy-2'-fluorobiphenyl + 5,6-dihydroxy-2,2'-difluorobiphenyl + NAD+ + HF - ? 186697 1.14.12.18 2,2'-difluorobiphenyl + NADH + O2 - Pseudomonas sp. LB400 2,3-dihydroxy-2'-fluorobiphenyl + 5,6-dihydroxy-2,2'-difluorobiphenyl + NAD+ + HF - ? 186697 1.14.12.18 2,2'-dihydroxybiphenyl + NADH + H+ + O2 - Burkholderia sp. ? - ? 375610 1.14.12.18 2,2'-dihydroxybiphenyl + NADH + H+ + O2 - Burkholderia sp. LB400 ? - ? 375610 1.14.12.18 2,2'-dihydroxybiphenyl + NADH + O2 - Pseudomonas sp. 2,3,2'-trihydroxybiphenyl + trihydroxybiphenyl + NAD+ - ? 186701 1.14.12.18 2,2'-dihydroxybiphenyl + NADH + O2 - Pseudomonas sp. LB400 2,3,2'-trihydroxybiphenyl + trihydroxybiphenyl + NAD+ - ? 186701 1.14.12.18 2,2'-dinitrobiphenyl + NADH + H+ + O2 - Burkholderia sp. ? - ? 375611 1.14.12.18 2,2'-dinitrobiphenyl + NADH + O2 - Pseudomonas sp. 2,3-dihydroxy-2'-nitrobiphenyl + NAD+ + NO2 - ? 186700 1.14.12.18 2,2'-dinitrobiphenyl + NADH + O2 - Pseudomonas sp. LB400 2,3-dihydroxy-2'-nitrobiphenyl + NAD+ + NO2 - ? 186700 1.14.12.18 2,3',4'-trichlorobiphenyl + NADH + O2 - Comamonas testosteroni ? - ? 375613 1.14.12.18 2,3',4-trichlorobiphenyl + NADH + H+ + O2 - Paraburkholderia xenovorans ? - ? 395360 1.14.12.18 2,3',4-trichlorobiphenyl + NADH + H+ + O2 - Pandoraea pnomenusa ? - ? 395360 1.14.12.18 2,3'-dichlorobiphenyl + NADH + H+ + O2 - Burkholderia sp. 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 - ? 375614 1.14.12.18 2,3'-dichlorobiphenyl + NADH + H+ + O2 - Burkholderia sp. LB400 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 - ? 375614 1.14.12.18 2,3'-dichlorobiphenyl + NADH + O2 - Pseudomonas sp. 5,6-dihydroxy-1-phenylcyclohexa-1,3-diene + 2,3-dihydroxy-3'-chlorobiphenyl + 5',6'-dihydroxy-1'-phenylcyclohexa-1',3'-diene + NAD+ + HCl - ? 186686 1.14.12.18 2,3,2',3'-tetrachlorobiphenyl + NADH + H+ + O2 oxygenated onto meta-para carbons 4 and 5 Paraburkholderia xenovorans 4,5-dihydro-4,5-dihydroxy-2,3,2',3'-tetrachlorobiphenyl + NAD+ - ? 375615 1.14.12.18 2,3,2',3'-tetrachlorobiphenyl + NADH + H+ + O2 - Paraburkholderia xenovorans cis-4,5-dihydro-4,5-dihydroxy-2,3,2',3'-tetrachlorobiphenyl + NAD+ - ? 375616 1.14.12.18 2,3,4'-trichlorobiphenyl + NADH + H+ + O2 - Paraburkholderia xenovorans ? - ? 395361 1.14.12.18 2,3,4'-trichlorobiphenyl + NADH + H+ + O2 - Pandoraea pnomenusa ? - ? 395361 1.14.12.18 2,3,4'-trichlorobiphenyl + NADH + O2 - Comamonas testosteroni ? - ? 375617 1.14.12.18 2,4',5-trichlorobiphenyl + NADH + H+ + O2 - Paraburkholderia xenovorans 3,4-dihydro-3,4-dihydroxy-2,5,4'-trichlorobiphenyl + 2',3'-dihydro-2',3'-dihydroxy-2,5,4'-trichlorobiphenyl + NAD+ - ? 387089 1.14.12.18 2,4'-dichlorobiphenyl + NADH + O2 - Pseudomonas sp. 2,3-dihydroxy-4'-chlorobiphenyl + NAD+ + HCl - ? 186692 1.14.12.18 2,4'-dichlorobiphenyl + NADH + O2 - Pseudomonas sp. LB400 2,3-dihydroxy-4'-chlorobiphenyl + NAD+ + HCl - ? 186692 1.14.12.18 2,4,2',4'-tetrachlorobiphenyl + NADH + H+ + O2 oxygenated principally onto vicinal ortho-meta carbons 2 and 3 Paraburkholderia xenovorans 2,3-dihydroxy-2',4,4'-trichlorobiphenyl + NAD+ + HCl - ? 375628 1.14.12.18 2,4,4'-trichlorobiphenyl + NADH + H+ + O2 - Paraburkholderia xenovorans 2,3-dihydro-2,3-dihydroxy-2',4,4'-trichlorobiphenyl + NAD+ - ? 395375 1.14.12.18 2,4,4'-trichlorobiphenyl + NADH + H+ + O2 - Pandoraea pnomenusa 2,3-dihydro-2,3-dihydroxy-2',4,4'-trichlorobiphenyl + NAD+ - ? 395375 1.14.12.18 2,5,2',5'-tetrachlorobiphenyl + NADH + O2 - Pseudomonas sp. 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 - ? 186690 1.14.12.18 2,5,2',5'-tetrachlorobiphenyl + NADH + O2 - Pseudomonas sp. LB400 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 - ? 186690 1.14.12.18 2,5,2'-trichlorobiphenyl + NADH + O2 - Pseudomonas sp. cis-3,4-dihydroxy-2,5-dichloro-1-[2'-chlorophenyl]-cyclohexa-1,5-diene + 2',3'-dihydroxy-2,5-dichlorobiphenyl + NAD+ + HCl - ? 186689 1.14.12.18 2,5,3'-trichlorobiphenyl + NADH + O2 - Pseudomonas sp. 3,4-dihydroxy-1-phenylcyclohexa-1,5-diene + 5',6'-dihydroxy-1'-phenylcyclohexa-1',3'-diene + 2,3-catechol + NAD+ + HCl - ? 186688 1.14.12.18 2,5,4'-trichlorobiphenyl + NADH + O2 - Pseudomonas oleovorans ? - ? 387098 1.14.12.18 2,5,4'-trichlorobiphenyl + NADH + O2 - Pseudomonas oleovorans KF707 ? - ? 387098 1.14.12.18 2,5-dichlorobiphenyl + NADH + O2 - Pseudomonas sp. cis-2',3'-dihydroxy-1'-(2,5-dichlorophenyl)-cyclohexa-4',6'-diene + 3,4-dihydroxy-1-phenylcyclohexa-1,5-diene + NAD+ + HCl - ? 186684 1.14.12.18 2,5-dichlorobiphenyl + NADH + O2 - Rhodococcus globerulus cis-2',3'-dihydroxy-1'-(2,5-dichlorophenyl)-cyclohexa-4',6'-diene + 3,4-dihydroxy-1-phenylcyclohexa-1,5-diene + NAD+ + HCl - ? 186684 1.14.12.18 2,5-dichlorobiphenyl + NADH + O2 no 3,4-dihydrodiol as product Comamonas testosteroni cis-2',3'-dihydroxy-1'-(2,5-dichlorophenyl)-cyclohexa-4',6'-diene + 3,4-dihydroxy-1-phenylcyclohexa-1,5-diene + NAD+ + HCl - ? 186684 1.14.12.18 2,5-dichlorobiphenyl + NADH + O2 - Rhodococcus globerulus P6 cis-2',3'-dihydroxy-1'-(2,5-dichlorophenyl)-cyclohexa-4',6'-diene + 3,4-dihydroxy-1-phenylcyclohexa-1,5-diene + NAD+ + HCl - ? 186684 1.14.12.18 2,5-dichlorobiphenyl + NADH + O2 - Pseudomonas sp. LB400 cis-2',3'-dihydroxy-1'-(2,5-dichlorophenyl)-cyclohexa-4',6'-diene + 3,4-dihydroxy-1-phenylcyclohexa-1,5-diene + NAD+ + HCl - ? 186684 1.14.12.18 2,6',4'-trichlorobiphenyl + NADH + O2 - Paraburkholderia xenovorans ? - ? 387101 1.14.12.18 2,6-dichlorobiphenyl + NADH + H+ + O2 - Paraburkholderia xenovorans 2,6-dichloro-2',3'-dihydro-2',3'-dihydroxybiphenyl + ? - ? 395400 1.14.12.18 2,6-dichlorobiphenyl + NADH + H+ + O2 - Pandoraea pnomenusa 2,6-dichloro-2',3'-dihydro-2',3'-dihydroxybiphenyl + ? - ? 395400 1.14.12.18 2,6-dichlorobiphenyl + NADH + H+ + O2 poor substrate Paraburkholderia xenovorans ? - ? 413898 1.14.12.18 2-chlorobiphenyl + NADH + O2 - Pseudomonas sp. cis-2',3'-dihydroxy-1'-(2-chlorophenyl)-cyclohexa-4',6'-diene + catechol + NAD+ - ? 186682 1.14.12.18 2-chlorobiphenyl + NADH + O2 no catechol formation Rhodococcus globerulus cis-2',3'-dihydroxy-1'-(2-chlorophenyl)-cyclohexa-4',6'-diene + catechol + NAD+ - ? 186682 1.14.12.18 2-chlorobiphenyl + NADH + O2 no catechol formation Rhodococcus globerulus P6 cis-2',3'-dihydroxy-1'-(2-chlorophenyl)-cyclohexa-4',6'-diene + catechol + NAD+ - ? 186682 1.14.12.18 2-chlorobiphenyl + NADH + O2 - Pseudomonas sp. LB400 cis-2',3'-dihydroxy-1'-(2-chlorophenyl)-cyclohexa-4',6'-diene + catechol + NAD+ - ? 186682 1.14.12.18 2-hydroxy-3,5-dichlorobiphenyl + NADH + H+ + O2 ortho-meta-oxygenation, hydroxylation on the non-substituted ring Comamonas testosteroni ? - ? 375676 1.14.12.18 2-hydroxy-3,5-dichlorobiphenyl + NADH + H+ + O2 ortho-meta-oxygenation, hydroxylation on the non-substituted ring Burkholderia sp. ? - ? 375676 1.14.12.18 2-hydroxy-3,5-dichlorobiphenyl + NADH + H+ + O2 ortho-meta-oxygenation, hydroxylation on the non-substituted ring Burkholderia sp. LB400 ? - ? 375676 1.14.12.18 2-hydroxy-3-chlorobiphenyl + NADH + H+ + O2 ortho-meta-oxygenation, hydroxylation on the non-substituted ring Comamonas testosteroni 5-(3-chloro-2-hydroxyphenyl)-6-hydroxy-3-cyclohexen-1-one + NAD+ + 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 ? 375677 1.14.12.18 2-hydroxy-3-chlorobiphenyl + NADH + H+ + O2 ortho-meta-oxygenation, hydroxylation on the non-substituted ring Burkholderia sp. 5-(3-chloro-2-hydroxyphenyl)-6-hydroxy-3-cyclohexen-1-one + NAD+ + 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 ? 375677 1.14.12.18 2-hydroxy-3-chlorobiphenyl + NADH + H+ + O2 ortho-meta-oxygenation, hydroxylation on the non-substituted ring Burkholderia sp. LB400 5-(3-chloro-2-hydroxyphenyl)-6-hydroxy-3-cyclohexen-1-one + NAD+ + 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 ? 375677 1.14.12.18 2-hydroxy-5-chlorobiphenyl + NADH + H+ + O2 ortho-meta-oxygenation, hydroxylation on the non-substituted ring Comamonas testosteroni 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+ 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 ? 375678 1.14.12.18 2-hydroxy-5-chlorobiphenyl + NADH + H+ + O2 ortho-meta-oxygenation, hydroxylation on the non-substituted ring Burkholderia sp. 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+ 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 ? 375678 1.14.12.18 2-hydroxy-5-chlorobiphenyl + NADH + H+ + O2 ortho-meta-oxygenation, hydroxylation on the non-substituted ring Burkholderia sp. LB400 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+ 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 ? 375678 1.14.12.18 3,3'-dichlorobiphenyl + NADH + H+ + O2 - Pseudomonas sp. ? - ? 375768 1.14.12.18 3,3'-dichlorobiphenyl + NADH + H+ + O2 - Paraburkholderia xenovorans ? - ? 375768 1.14.12.18 3,3'-dichlorobiphenyl + NADH + H+ + O2 - Pandoraea pnomenusa ? - ? 375768 1.14.12.18 3,3'-dichlorobiphenyl + NADH + H+ + O2 wild-type enzyme Comamonas testosteroni ? - ? 375768 1.14.12.18 3,3'-dichlorobiphenyl + NADH + H+ + O2 - Pandoraea pnomenusa B-356 ? - ? 375768 1.14.12.18 3,3'-dichlorobiphenyl + NADH + H+ + O2 - Comamonas testosteroni 5,6-dihydroxy-1-phenylcyclohexa-1,3-diene + 4,5-dihydroxy-1-phenylcyclohexa-1,2-diene + NAD+ + HCl - ? 407940 1.14.12.18 3,3'-dichlorobiphenyl + NADH + O2 - Pseudomonas sp. 5,6-dihydroxy-1-phenylcyclohexa-1,3-diene + 4,5-dihydroxy-1-phenylcyclohexa-1,2-diene + NAD+ + HCl - ? 186687 1.14.12.18 3,3'-dichlorobiphenyl + NADH + O2 - Comamonas testosteroni 5,6-dihydroxy-1-phenylcyclohexa-1,3-diene + 4,5-dihydroxy-1-phenylcyclohexa-1,2-diene + NAD+ + HCl - ? 186687 1.14.12.18 3,3'-dichlorobiphenyl + NADH + O2 - Rhodococcus globerulus 5,6-dihydroxy-1-phenylcyclohexa-1,3-diene + 4,5-dihydroxy-1-phenylcyclohexa-1,2-diene + NAD+ + HCl - ? 186687 1.14.12.18 3,3'-dichlorobiphenyl + NADH + O2 - Paraburkholderia xenovorans 5,6-dihydroxy-1-phenylcyclohexa-1,3-diene + 4,5-dihydroxy-1-phenylcyclohexa-1,2-diene + NAD+ + HCl - ? 186687 1.14.12.18 3,3'-dichlorobiphenyl + NADH + O2 poor substrate Pseudomonas sp. 5,6-dihydroxy-1-phenylcyclohexa-1,3-diene + 4,5-dihydroxy-1-phenylcyclohexa-1,2-diene + NAD+ + HCl - ? 186687 1.14.12.18 3,3'-dichlorobiphenyl + NADH + O2 - Rhodococcus globerulus P6 5,6-dihydroxy-1-phenylcyclohexa-1,3-diene + 4,5-dihydroxy-1-phenylcyclohexa-1,2-diene + NAD+ + HCl - ? 186687 1.14.12.18 3,3'-dichlorobiphenyl + NADH + O2 - Pseudomonas sp. LB400 5,6-dihydroxy-1-phenylcyclohexa-1,3-diene + 4,5-dihydroxy-1-phenylcyclohexa-1,2-diene + NAD+ + HCl - ? 186687 1.14.12.18 3,3'-dichlorobiphenyl + NADH + O2 - Comamonas testosteroni ? - ? 375769 1.14.12.18 3,4'-dichlorobiphenyl + NAD(P)H + O2 - Rhodococcus globerulus 5,6-dihydroxy-3,4'-dichlorobiphenyl + NAD(P)+ - ? 186693 1.14.12.18 3,4'-dichlorobiphenyl + NAD(P)H + O2 - Rhodococcus globerulus P6 5,6-dihydroxy-3,4'-dichlorobiphenyl + NAD(P)+ - ? 186693 1.14.12.18 3,4'-dichlorobiphenyl + NADH + H+ + O2 - Burkholderia sp. 3-chloro-5-(4-chlorophenyl)cyclohexa-3,5-diene-1,2-diol + 3-chloro-6-(3-chlorophenyl)cyclohexa-3,4-diene-1,2-diol - ? 375772 1.14.12.18 3,4'-dichlorobiphenyl + NADH + H+ + O2 - Burkholderia sp. LB400 3-chloro-5-(4-chlorophenyl)cyclohexa-3,5-diene-1,2-diol + 3-chloro-6-(3-chlorophenyl)cyclohexa-3,4-diene-1,2-diol - ? 375772 1.14.12.18 3,4,4'-trichlorobiphenyl + NADH + O2 - Paraburkholderia xenovorans ? - ? 387302 1.14.12.18 3,5',4'-trichlorobiphenyl + NADH + O2 - Paraburkholderia xenovorans ? - ? 387316 1.14.12.18 3-chlorobiphenyl + NADH + O2 - Pseudomonas sp. cis-2',3'-dihydroxy-1'-(3-chlorophenyl)-cyclohexa-4',6'-diene + NAD+ - ? 186683 1.14.12.18 3-chlorobiphenyl + NADH + O2 - Rhodococcus globerulus cis-2',3'-dihydroxy-1'-(3-chlorophenyl)-cyclohexa-4',6'-diene + NAD+ - ? 186683 1.14.12.18 3-chlorobiphenyl + NADH + O2 - Rhodococcus globerulus P6 cis-2',3'-dihydroxy-1'-(3-chlorophenyl)-cyclohexa-4',6'-diene + NAD+ - ? 186683 1.14.12.18 3-chlorobiphenyl + NADH + O2 - Pseudomonas sp. LB400 cis-2',3'-dihydroxy-1'-(3-chlorophenyl)-cyclohexa-4',6'-diene + NAD+ - ? 186683 1.14.12.18 4,4'-dichlorobiphenyl + NAD(P)H + O2 - Pseudomonas oleovorans 2,3-dihydroxy-4,4'-dichlorobiphenyl + NAD(P)+ - ? 186694 1.14.12.18 4,4'-dichlorobiphenyl + NAD(P)H + O2 - Rhodococcus globerulus 2,3-dihydroxy-4,4'-dichlorobiphenyl + NAD(P)+ - ? 186694 1.14.12.18 4,4'-dichlorobiphenyl + NAD(P)H + O2 - Rhodococcus globerulus P6 2,3-dihydroxy-4,4'-dichlorobiphenyl + NAD(P)+ - ? 186694 1.14.12.18 4,4'-dichlorobiphenyl + NAD(P)H + O2 - Pseudomonas oleovorans KF707 2,3-dihydroxy-4,4'-dichlorobiphenyl + NAD(P)+ - ? 186694 1.14.12.18 4,4'-dichlorobiphenyl + NADH + H+ + O2 - Pseudomonas sp. ? - ? 375857 1.14.12.18 4,4'-dichlorobiphenyl + NADH + H+ + O2 - Burkholderia sp. ? - ? 375857 1.14.12.18 4,4'-dichlorobiphenyl + NADH + H+ + O2 - Paraburkholderia xenovorans ? - ? 375857 1.14.12.18 4,4'-dichlorobiphenyl + NADH + H+ + O2 - Pandoraea pnomenusa ? - ? 375857 1.14.12.18 4,4'-dichlorobiphenyl + NADH + H+ + O2 - Pandoraea pnomenusa B-356 ? - ? 375857 1.14.12.18 4,4'-dichlorobiphenyl + NADH + H+ + O2 - Comamonas testosteroni 2,3-dihydroxy-4,4'-dichlorobiphenyl + NAD+ - ? 408050 1.14.12.18 4-chlorobiphenyl + NADH + O2 - Pseudomonas sp. 2',3'-dihydrodiol-4-chlorobiphenyl + NAD+ - ? 186691 1.14.12.18 4-chlorobiphenyl + NADH + O2 - Rhodococcus globerulus 2',3'-dihydrodiol-4-chlorobiphenyl + NAD+ - ? 186691 1.14.12.18 4-chlorobiphenyl + NADH + O2 - Rhodococcus globerulus P6 2',3'-dihydrodiol-4-chlorobiphenyl + NAD+ - ? 186691 1.14.12.18 4-chlorobiphenyl + NADH + O2 - Pseudomonas sp. LB400 2',3'-dihydrodiol-4-chlorobiphenyl + NAD+ - ? 186691 1.14.12.18 4-methylbiphenyl + NADH + O2 - Pseudomonas oleovorans 2-hydroxy-6-oxo-6-[4-methylphenyl]-hexa-2,4-dienoic acid + NAD+ - ? 387498 1.14.12.18 4-methylbiphenyl + NADH + O2 - Pseudomonas oleovorans KF707 2-hydroxy-6-oxo-6-[4-methylphenyl]-hexa-2,4-dienoic acid + NAD+ - ? 387498 1.14.12.18 5,7-dihydroxyflavone + NADH + H+ + O2 BphA1 (1-22) and BphA1 (2-2), expression of the mutants in together with bphA2A3A4B from strain KF707 Pseudomonas putida 2-(2,3-dihydroxyphenyl)-5,7-dihydroxy-chromen-4-one + NAD+ - ? 399735 1.14.12.18 5,7-dihydroxyflavone + NADH + H+ + O2 BphA1 (1-22) and BphA1 (2-2), expression of the mutants in together with bphA2A3A4B from strain KF707 Pseudomonas putida KF715 2-(2,3-dihydroxyphenyl)-5,7-dihydroxy-chromen-4-one + NAD+ - ? 399735 1.14.12.18 6,7-dihydro-5H-benzocycloheptene + NAD(P)H + O2 - Sphingobium yanoikuyae (-)-cis-(1R,2S)-dihydroxybenzocycloheptane + NAD(P)+ - ? 186696 1.14.12.18 6,7-dihydro-5H-benzocycloheptene + NAD(P)H + O2 - Sphingobium yanoikuyae B8/36 (-)-cis-(1R,2S)-dihydroxybenzocycloheptane + NAD(P)+ - ? 186696 1.14.12.18 6-hydroxyflavanone + O2 + NAD(P)H - Pseudomonas oleovorans ? - ? 387632 1.14.12.18 6-hydroxyflavanone + O2 + NAD(P)H - Pseudomonas oleovorans KF707 ? - ? 387632 1.14.12.18 7-hydroxyflavanone + O2 + NAD(P)H - Pseudomonas oleovorans ? - ? 387662 1.14.12.18 7-hydroxyflavanone + O2 + NAD(P)H - Pseudomonas oleovorans KF707 ? - ? 387662 1.14.12.18 7-hydroxyflavone + NADH + H+ + O2 BphA1 (1-22) and BphA1 (2-2), expression of the mutants together with bphA2A3A4B from strain KF707 Pseudomonas putida 2-(2,3-dihydroxyphenyl)-7-hydroxy-chromen-4-one + NAD+ - ? 399775 1.14.12.18 7-hydroxyflavone + NADH + H+ + O2 BphA1 (1-22) and BphA1 (2-2), expression of the mutants together with bphA2A3A4B from strain KF707 Pseudomonas putida KF715 2-(2,3-dihydroxyphenyl)-7-hydroxy-chromen-4-one + NAD+ - ? 399775 1.14.12.18 benzene + ? benzene is only a substrate for Pseudomonas pseudoalcaligenes strain 1072 Pseudomonas oleovorans ? - ? 388176 1.14.12.18 benzo[a]pyrene + NADH + O2 - Sphingobium yanoikuyae ? - ? 388188 1.14.12.18 benzo[a]pyrene + NADH + O2 - Sphingobium yanoikuyae B1 ? - ? 388188 1.14.12.18 biphenyl + NAD(P)H + O2 - Sphingobium yanoikuyae (1S,2R)-dihydroxy-3-phenylcyclohexa-3,5-diene + NAD(P)+ - ? 186678 1.14.12.18 biphenyl + NAD(P)H + O2 - Sphingobium yanoikuyae B8/36 (1S,2R)-dihydroxy-3-phenylcyclohexa-3,5-diene + NAD(P)+ - ? 186678 1.14.12.18 biphenyl + NAD(P)H + O2 - Pseudomonas sp. cis-biphenyl 2,3-dihydrodiol + NAD(P)+ - ? 186679 1.14.12.18 biphenyl + NAD(P)H + O2 - Pseudomonas oleovorans cis-biphenyl 2,3-dihydrodiol + NAD(P)+ - ? 186679 1.14.12.18 biphenyl + NAD(P)H + O2 - Sphingobium yanoikuyae cis-biphenyl 2,3-dihydrodiol + NAD(P)+ - ? 186679 1.14.12.18 biphenyl + NAD(P)H + O2 - Paraburkholderia xenovorans cis-biphenyl 2,3-dihydrodiol + NAD(P)+ - ? 186679 1.14.12.18 biphenyl + NAD(P)H + O2 - Pseudomonas sp. LB400 cis-biphenyl 2,3-dihydrodiol + NAD(P)+ - ? 186679 1.14.12.18 biphenyl + NAD(P)H + O2 - Pseudomonas oleovorans KF707 cis-biphenyl 2,3-dihydrodiol + NAD(P)+ - ? 186679 1.14.12.18 biphenyl + NAD(P)H + O2 - Sphingobium yanoikuyae B1 cis-biphenyl 2,3-dihydrodiol + NAD(P)+ - ? 186679 1.14.12.18 biphenyl + NAD(P)H + O2 - Bacteria 2,3-dihydro-dihydroxybiphenyl + NAD(P)+ - ? 186680 1.14.12.18 biphenyl + NAD(P)H + O2 - Comamonas testosteroni 2,3-dihydro-dihydroxybiphenyl + NAD(P)+ - ? 186680 1.14.12.18 biphenyl + NAD(P)H + O2 - Rhodococcus globerulus 2,3-dihydro-dihydroxybiphenyl + NAD(P)+ - ? 186680 1.14.12.18 biphenyl + NAD(P)H + O2 - Rhodococcus globerulus P6 2,3-dihydro-dihydroxybiphenyl + NAD(P)+ - ? 186680 1.14.12.18 biphenyl + NADH + H+ + O2 - Burkholderia sp. ? - ? 376417 1.14.12.18 biphenyl + NADH + H+ + O2 wild-type enzyme Comamonas testosteroni ? - ? 376417 1.14.12.18 biphenyl + NADH + H+ + O2 - Pseudomonas sp. (1S,2R)-3-phenylcyclohexa-3,5-diene-1,2-diol + NAD+ + ? - ? 396615 1.14.12.18 biphenyl + NADH + H+ + O2 - Pseudomonas oleovorans 2,3-dihydro-dihydroxybiphenyl + NAD+ - ? 408786 1.14.12.18 biphenyl + NADH + H+ + O2 - Paraburkholderia xenovorans 2,3-dihydro-dihydroxybiphenyl + NAD+ - ? 408786 1.14.12.18 biphenyl + NADH + H+ + O2 - Comamonas testosteroni 2,3-dihydro-dihydroxybiphenyl + NAD+ - ? 408786 1.14.12.18 biphenyl + NADH + H+ + O2 - Paraburkholderia xenovorans LB400 2,3-dihydro-dihydroxybiphenyl + NAD+ - ? 408786 1.14.12.18 biphenyl + NADH + H+ + O2 - Pseudomonas oleovorans KF707 2,3-dihydro-dihydroxybiphenyl + NAD+ - ? 408786 1.14.12.18 biphenyl + NADH + H+ + O2 - Paraburkholderia xenovorans cis-(2R,3S)-dihydroxy-1-phenylcyclohexa-4,6-diene + NAD+ - ? 413299 1.14.12.18 biphenyl + NADH + H+ + O2 - Enterobacter sp. (1S,2R)-3-phenylcyclohexa-3,5-diene-1,2-diol + NAD+ - ? 424691 1.14.12.18 biphenyl + NADH + H+ + O2 - Sphingobium yanoikuyae (1S,2R)-3-phenylcyclohexa-3,5-diene-1,2-diol + NAD+ - ? 424691 1.14.12.18 biphenyl + NADH + H+ + O2 - Paraburkholderia xenovorans (1S,2R)-3-phenylcyclohexa-3,5-diene-1,2-diol + NAD+ - ? 424691 1.14.12.18 biphenyl + NADH + H+ + O2 - Rhodococcus jostii (1S,2R)-3-phenylcyclohexa-3,5-diene-1,2-diol + NAD+ - ? 424691 1.14.12.18 biphenyl + NADH + H+ + O2 - Rhodococcus sp. G10 (1S,2R)-3-phenylcyclohexa-3,5-diene-1,2-diol + NAD+ - ? 424691 1.14.12.18 biphenyl + NADH + H+ + O2 - Sphingobium yanoikuyae B1 (1S,2R)-3-phenylcyclohexa-3,5-diene-1,2-diol + NAD+ - ? 424691 1.14.12.18 biphenyl + NADH + H+ + O2 - Enterobacter sp. LY402 (1S,2R)-3-phenylcyclohexa-3,5-diene-1,2-diol + NAD+ - ? 424691 1.14.12.18 biphenyl + NADH + O2 - Paraburkholderia xenovorans cis-biphenyl 2,3-dihydrodiol + NAD+ - ? 411804 1.14.12.18 biphenyl + NADH + O2 - Pandoraea pnomenusa cis-biphenyl 2,3-dihydrodiol + NAD+ - ? 411804 1.14.12.18 carbazole + NADH + O2 no products with carbazole detected Pseudomonas sp. 3-hydroxycarbazole + NAD+ - ? 186681 1.14.12.18 carbazole + NADH + O2 formation of an unstable cis-carbazole-3,4-dihydrodiol is proposed Sphingobium yanoikuyae 3-hydroxycarbazole + NAD+ - ? 186681 1.14.12.18 carbazole + NADH + O2 no products with carbazole detected Pseudomonas sp. LB400 3-hydroxycarbazole + NAD+ - ? 186681 1.14.12.18 carbazole + NADH + O2 formation of an unstable cis-carbazole-3,4-dihydrodiol is proposed Sphingobium yanoikuyae B8/36 3-hydroxycarbazole + NAD+ - ? 186681 1.14.12.18 dibenzo-p-dioxin + NADH + O2 - Comamonas testosteroni 2,2',3-trihydroxybiphenyl ether + NAD+ - ? 376687 1.14.12.18 dibenzo-p-dioxin + NADH + O2 - Paraburkholderia xenovorans 2,2',3-trihydroxybiphenyl ether + NAD+ - ? 376687 1.14.12.18 dibenzo-p-dioxine + NADH + O2 - Pseudomonas sp. 2,3,2'-trihydroxy-diphenylether + dibenzo-p-dioxine-dihydrodiol + NAD+ - ? 186703 1.14.12.18 dibenzofuran + NADH + O2 dibenzofuran is a poor substrate Pseudomonas oleovorans ? - ? 388530 1.14.12.18 dibenzofurane + NADH + O2 - Pseudomonas sp. monohydroxydibenzofuran + 2,3,2'-trihydroxybiphenyl + dibenzofuran-1,2-dihydrodiol + dibenzofuran-3,4-dihydrodiol + NAD+ - ? 186702 1.14.12.18 dibenzofurane + NADH + O2 - Comamonas testosteroni 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 ? 376688 1.14.12.18 dibenzofurane + NADH + O2 - Paraburkholderia xenovorans 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 ? 376688 1.14.12.18 diphenylmethane + NADH + O2 - Pseudomonas oleovorans ? - ? 388586 1.14.12.18 ethylbenzene + ? - Pseudomonas oleovorans ? - ? 388667 1.14.12.18 ethylbenzene + NADH + O2 - Paraburkholderia xenovorans ? - ? 375122 1.14.12.18 flavone + O2 + NAD(P)H - Pseudomonas oleovorans cis-flavone-2',3'-dihydrodiol + ? - ? 388693 1.14.12.18 flavone + O2 + NADH + H+ the flavone metabolite is 2-[(5S,6R)-5,6-dihydroxycyclohexa-1,3-dienyl]-4H-chromen-4-one Pseudomonas oleovorans cis-flavone-2',3'-dihydrodiol + ? - ? 409407 1.14.12.18 flavone + O2 + NADH + H+ the flavone metabolite is 2-[(5S,6R)-5,6-dihydroxycyclohexa-1,3-dienyl]-4H-chromen-4-one Pseudomonas oleovorans KF707 cis-flavone-2',3'-dihydrodiol + ? - ? 409407 1.14.12.18 isoflavone + NADH + H+ + O2 - Pseudomonas oleovorans isoflavone-cis-(2'R,3'S)-dihydrodiol + NAD+ - ? 414729 1.14.12.18 isoflavone + O2 + NADH + H+ 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 Pseudomonas oleovorans 2',3'-dihydro-2',3'-cis-dihydroxyflavone + NAD+ - ? 409609 1.14.12.18 isoflavone + O2 + NADH + H+ 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 Pseudomonas oleovorans KF707 2',3'-dihydro-2',3'-cis-dihydroxyflavone + NAD+ - ? 409609 1.14.12.18 additional information no substrates are benzene, toluene, 2,5-dichlorotoluene, carbazole and dibenzothiophene Pseudomonas sp. ? - ? 89 1.14.12.18 additional information overview on polychlorinated biphenyls Pseudomonas sp. ? - ? 89 1.14.12.18 additional information overview on polychlorinated biphenyls Pseudomonas oleovorans ? - ? 89 1.14.12.18 additional information enzyme of biphenyl catabolic pathway Burkholderia sp. ? - ? 89 1.14.12.18 additional information no activity with 3,3'-dichlorobiphenyl Burkholderia sp. ? - ? 89 1.14.12.18 additional information no activity with 4,4'-dichlorobiphenyl and 2,2',5,5'-tetrachlorobiphenyl Comamonas testosteroni ? - ? 89 1.14.12.18 additional information no activity on toluene and benzene Paraburkholderia xenovorans ? - ? 89 1.14.12.18 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 Pseudomonas oleovorans ? - ? 89 1.14.12.18 additional information the enzyme does not produce metabolites from 2'-hydroxyflavanone, 3'-hydroxyflavanone, and naringenin Pseudomonas oleovorans ? - ? 89 1.14.12.18 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 Sphingobium yanoikuyae ? - ? 89 1.14.12.18 additional information a single multicomponent dioxygenase enzyme is involved in the initial oxidation of both biphenyl and naphthalene in Sphingobium yanoikuyae strain B1 Sphingobium yanoikuyae ? - ? 89 1.14.12.18 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 Pseudomonas putida ? - ? 89 1.14.12.18 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 Paraburkholderia xenovorans LB400 ? - ? 89 1.14.12.18 additional information Phe378 and Phe384 are near the substrate inside the catalytic pocket and thus likely interact with it Rhodococcus jostii RHA1 ? - ? 89 1.14.12.18 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 Pseudomonas oleovorans ? - ? 89 1.14.12.18 additional information the strain LY402 shows polychlorinated biphenyls degradation abilities of BphA1, molecular simulation and ligand docking studies, overview Enterobacter sp. ? - ? 89 1.14.12.18 additional information overview on polychlorinated biphenyls Pseudomonas sp. LB400 ? - ? 89 1.14.12.18 additional information no substrates are benzene, toluene, 2,5-dichlorotoluene, carbazole and dibenzothiophene Pseudomonas sp. LB400 ? - ? 89 1.14.12.18 additional information overview on polychlorinated biphenyls Pseudomonas oleovorans KF707 ? - ? 89 1.14.12.18 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 Pseudomonas oleovorans KF707 ? - ? 89 1.14.12.18 additional information the enzyme does not produce metabolites from 2'-hydroxyflavanone, 3'-hydroxyflavanone, and naringenin Pseudomonas oleovorans KF707 ? - ? 89 1.14.12.18 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 Pseudomonas oleovorans KF707 ? - ? 89 1.14.12.18 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 Pseudomonas putida KF715 ? - ? 89 1.14.12.18 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 Sphingobium yanoikuyae B1 ? - ? 89 1.14.12.18 additional information a single multicomponent dioxygenase enzyme is involved in the initial oxidation of both biphenyl and naphthalene in Sphingobium yanoikuyae strain B1 Sphingobium yanoikuyae B1 ? - ? 89 1.14.12.18 additional information enzyme of biphenyl catabolic pathway Burkholderia sp. LB400 ? - ? 89 1.14.12.18 additional information the strain LY402 shows polychlorinated biphenyls degradation abilities of BphA1, molecular simulation and ligand docking studies, overview Enterobacter sp. LY402 ? - ? 89 1.14.12.18 naphthalene + NADH + O2 - Sphingobium yanoikuyae ? - ? 389368 1.14.12.18 naphthalene + NADH + O2 - Sphingobium yanoikuyae B1 ? - ? 389368 1.14.12.18 naphthalene + NADPH + O2 poor substrate Pseudomonas sp. cis-naphthalene 1,2-dihydrodiol + NADP+ - ? 186695 1.14.12.18 naphthalene + NADPH + O2 poor substrate Pseudomonas sp. LB400 cis-naphthalene 1,2-dihydrodiol + NADP+ - ? 186695 1.14.12.18 phenanthrene + NADH + O2 - Sphingobium yanoikuyae ? - ? 389534 1.14.12.18 phenanthrene + NADH + O2 - Sphingobium yanoikuyae B1 ? - ? 389534 1.14.12.18 phenazine + NADH + H+ + O2 - Sphingobium yanoikuyae 1,2-dihydro-1,2-dihydroxyphenazine + NAD+ - ? 441859 1.14.12.18 phenazine + NADH + H+ + O2 - Sphingobium yanoikuyae B1 1,2-dihydro-1,2-dihydroxyphenazine + NAD+ - ? 441859 1.14.12.18 toluene + NAD(P)H + O2 toluene is only a substrate for Pseudomonas pseudoalcaligenes strain 1072 Pseudomonas oleovorans ? - ? 389902