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biphenyl + NADH + H+ + O2
(1S,2R)-3-phenylcyclohexa-3,5-diene-1,2-diol + 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',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'-dichlorobiphenyl + NADH + H+ + O2
2,3-dihydroxy-2'-chlorobiphenyl + 3,4-dihydro-3,4-dihydroxy-2,2'-dichlorobiphenyl + NAD+ + HCl
2,2'-dichlorobiphenyl + NADH + H+ + O2
2,3-dihydroxy-2'-chlorobiphenyl + cis-3,4-dihydro-3,4-dihydroxy-2,2'-dichlorobiphenyl + NAD+ + HCl
-
-
-
-
?
2,2'-dichlorobiphenyl + NADH + H+ + O2
2,3-dihydroxy-2'-chlorobiphenyl + NAD+ + HCl
-
poor substrate
-
-
?
2,2'-dichlorobiphenyl + NADH + H+ + O2
?
-
-
-
-
?
2,3',4-trichlorobiphenyl + NADH + H+ + O2
?
-
-
-
-
?
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
?
-
-
-
-
?
2,4',5-trichlorobiphenyl + NADH + H+ + O2
3,4-dihydro-3,4-dihydroxy-2,5,4'-trichlorobiphenyl + 2',3'-dihydro-2',3'-dihydroxy-2,5,4'-trichlorobiphenyl + NAD+
-
-
-
-
?
2,4,2',4'-tetrachlorobiphenyl + NADH + H+ + O2
2,3-dihydroxy-2',4,4'-trichlorobiphenyl + NAD+ + HCl
-
oxygenated principally onto vicinal ortho-meta carbons 2 and 3
-
-
?
2,4,4'-trichlorobiphenyl + NADH + H+ + O2
2,3-dihydro-2,3-dihydroxy-2',4,4'-trichlorobiphenyl + NAD+
-
-
-
-
?
2,6',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
-
-
?
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
-
-
-
-
?
3,4,4'-trichlorobiphenyl + NADH + O2
?
-
-
-
-
?
3,5',4'-trichlorobiphenyl + NADH + O2
?
-
-
-
-
?
4,4'-dichlorobiphenyl + NADH + H+ + O2
?
-
-
-
-
?
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
2,3-dihydro-dihydroxybiphenyl + NAD+
-
-
-
?
biphenyl + NADH + H+ + O2
cis-(2R,3S)-dihydroxy-1-phenylcyclohexa-4,6-diene + NAD+
-
-
-
-
?
biphenyl + NADH + O2
cis-biphenyl 2,3-dihydrodiol + 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
-
?
ethylbenzene + NADH + O2
?
-
-
-
-
?
additional information
?
-
-
no activity on toluene and benzene
-
-
?
2,2'-dichlorobiphenyl + NADH + H+ + O2
2,3-dihydroxy-2'-chlorobiphenyl + 3,4-dihydro-3,4-dihydroxy-2,2'-dichlorobiphenyl + NAD+ + HCl
-
-
-
-
?
2,2'-dichlorobiphenyl + NADH + H+ + O2
2,3-dihydroxy-2'-chlorobiphenyl + 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
-
?
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purified recombinant BPDOLB400, sitting drop vapour diffusion method, anaerobic conditions, method optimization, 0.002 ml of 8 mg/ml protein in 25 mM HEPES, pH 7.3, containing 0.25 mM ferrous ammonium sulfate, and 2 mM dithiothreitol, is mixed with 0.002 ml of reservoir solution containing 20-25% w/v PEG 8000 or PEG 5000 MME, 50 mM PIPES, pH 6.5, 100 mM ammonium acetate, 5% v/v glycerol, and 0.2% w/v agarose, successful crystallization only occurs at pH 6.5, X-ray diffraction structure determination and analysis at 2.4-2.8 A resolution
crystal structure of the BPDOB356/2,6-dichlorobiphenyl complex is determined at 2.4 A resolution
-
purified recombinant BPDOLB400, sitting drop vapour diffusion method, anaerobic conditions, method optimization, 0.002 ml of 8 mg/ml protein in 25 mM HEPES, pH 7.3, containing 0.25 mM ferrous ammonium sulfate, and 2 mM dithiothreitol, is mixed with 0.002 ml of reservoir solution containing 20-25% w/v PEG 8000 or PEG 5000 MME, 50 mM PIPES, pH 6.5, 100 mM ammonium acetate, 5% v/v glycerol, and 0.2% w/v agarose, successful crystallization only occurs at pH 6.5, X-ray diffraction structure determination and analysis at 2.4-2.8 A resolution
sitting drop vapor diffusion method, using 20-25% (w/v) PEG 8000 or PEG 5000 MME, 50 mM PIPES pH 6.5, 100 mM ammonium acetate, 5% (v/v) glycerol and 0.2% (w/v) agarose
sitting drop vapor diffusion method, using 2025% (w/v) PEG 8000 or PEG 5000 MME, 50 mM PIPES (pH 6.5), 100 mM ammonium acetate, 5% (v/v) glycerol, and 0.2% (w/v) agarose
-
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F336M
-
the mutant produces principally 3,4-dihydro-3,4-dihydroxy-2,2'-dichlorobiphenyl from 2,2'-dichlorobiphenyl
F370Y
-
lower reactivity toward 2,2-dichlorobiphenyl but unchanged regiospecificity toward this substrate compared to the wild type enzyme
L283S
-
lower reactivity toward 2,2-dichlorobiphenyl but unchanged regiospecificity toward this substrate compared to the wild type enzyme
M237T
-
lower reactivity toward 2,2-dichlorobiphenyl but unchanged regiospecificity toward this substrate compared to the wild type enzyme
S238T
-
lower reactivity toward 2,2-dichlorobiphenyl but unchanged regiospecificity toward this substrate compared to the wild type enzyme
T335A/F336I
-
the ratio of the product formed from 2,2'-dichlorobiphenyl, 2,3-dihydroxy-2'-chlorobiphenyl to 3,4-dihydro-3,4-dihydroxy-2,2'-dichlorobiphenyl is: 90/10 for the wild-type enzyme and 40/60 for the mutant enzymes
T335A/F336L
-
the ratio of the product formed from 2,2'-dichlorobiphenyl, 2,3-dihydroxy-2'-chlorobiphenyl to 3,4-dihydro-3,4-dihydroxy-2,2'-dichlorobiphenyl is: 90/10 for the wild-type enzyme and 85/15 for the mutant enzymes
T335A/F336L/I341V
-
the ratio of the product formed from 2,2'-dichlorobiphenyl, 2,3-dihydroxy-2'-chlorobiphenyl to 3,4-dihydro-3,4-dihydroxy-2,2'-dichlorobiphenyl is: 90/10 for the wild-type enzyme and 40/60 for the mutant enzymes
T335G
-
the ratio of the product formed from 2,2'-dichlorobiphenyl, 2,3-dihydroxy-2'-chlorobiphenyl to 3,4-dihydro-3,4-dihydroxy-2,2'-dichlorobiphenyl is: 90/10 for the wild-type enzyme and 80/20 for the mutant enzymes
T377N
-
lower reactivity toward 2,2-dichlorobiphenyl but unchanged regiospecificity toward this substrate compared to the wild type enzyme
T335A
-
the ratio of the product formed from 2,2'-dichlorobiphenyl, 2,3-dihydroxy-2'-chlorobiphenyl to 3,4-dihydro-3,4-dihydroxy-2,2'-dichlorobiphenyl is: 90/10 for the wild-type enzyme and 85/15 for the mutant enzymes
T335A
-
the mutant yields 2,3-dihydroxy-2,2'chlorobiphenyl as the major metabolite from 2,2'-dichlorobiphenyl
T335A/F336M
-
the ratio of the product formed from 2,2'-dichlorobiphenyl, 2,3-dihydroxy-2'-chlorobiphenyl to 3,4-dihydro-3,4-dihydroxy-2,2'-dichlorobiphenyl is: 90/10 for the wild-type enzyme and 40/60 for the mutant enzymes
T335A/F336M
-
the mutant metabolizes 2,2'-dichlorobiphenyl better than the wild type enzyme to generate principally 3,4-dihydro-3,4-dihydroxy-2,2'-dichlorobiphenyl instead of 2,3-dihydroxy-2'-chlorobiphenyl as produced by the wild type enzyme, the mutant produces 3',4'-dihydroxy-3',4'-dihydro-2,6-dichlorobiphenyl as a major metabolite from 2,6-dichlorobiphenyl
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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.; 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
Zielinski, M.; Kahl, S.; Standfuss-Gabisch, C.; Camara, B.; Seeger, M.; Hofer, B.
Generation of novel-substrate-accepting biphenyl dioxygenases through segmental random mutagenesis and identification of residues involved in enzyme specificity
Appl. Environ. Microbiol.
72
2191-2199
2006
Paraburkholderia xenovorans
brenda
Witzig, R.; Junca, H.; Hecht, H.J.; Pieper, D.H.
Assessment of toluene/biphenyl dioxygenase gene diversity in benzene-polluted soils: links between benzene biodegradation and genes similar to those encoding isopropylbenzene dioxygenases
Appl. Environ. Microbiol.
72
3504-3514
2006
Pseudomonas aeruginosa, Burkholderia sp. (O86136), Paraburkholderia xenovorans (P37333), Comamonas testosteroni (Q46372), Comamonas testosteroni (Q8KZP9), Pseudomonas oleovorans (Q52028), Pseudomonas sp. (Q52438), Rhodococcus globerulus (Q52757), Rhodococcus sp. (Q53122), Rhodococcus erythropolis (Q79EP8), Pseudomonas aeruginosa JI104, Rhodococcus globerulus P6 (Q52757), Pseudomonas oleovorans KF707 (Q52028), Rhodococcus erythropolis TA421 (Q79EP8)
brenda
Suenaga, H.; Sato, M.; Goto, M.; Takeshita, M.; Furukawa, K.
Steady-state kinetic characterization of evolved biphenyl dioxygenase, which acquired novel degradation ability for benzene and toluene
Biosci. Biotechnol. Biochem.
70
1021-1025
2006
Pseudomonas oleovorans, Paraburkholderia xenovorans
brenda
Vezina, J.; Barriault, D.; Sylvestre, M.
Family shuffling of soil DNA to change the regiospecificity of Burkholderia xenovorans LB400 biphenyl dioxygenase
J. Bacteriol.
189
779-788
2007
Paraburkholderia xenovorans
brenda
Mohammadi, M.; Chalavi, V.; Novakova-Sura, M.; Laliberte, J.; Sylvestre, M.
Expression of bacterial biphenyl-chlorobiphenyl dioxygenase genes in tobacco plants
Biotechnol. Bioeng.
97
496-505
2007
Paraburkholderia xenovorans
brenda
Gomez-Gil, L.; Kumar, P.; Barriault, D.; Bolin, J.T.; Sylvestre, M.; Eltis, L.D.
Characterization of biphenyl dioxygenase of Pandoraea pnomenusa B-356 as a potent polychlorinated biphenyl-degrading enzyme
J. Bacteriol.
189
5705-5715
2007
Paraburkholderia xenovorans, Pandoraea pnomenusa, Pandoraea pnomenusa B-356
brenda
Kumar, P.; Gomez-Gil, L.; Mohammadi, M.; Sylvestre, M.; Eltis, L.D.; Bolin, J.T.
Anaerobic crystallization and initial X-ray diffraction data of biphenyl 2,3-dioxygenase from Burkholderia xenovorans LB400: addition of agarose improved the quality of the crystals
Acta Crystallogr. Sect. F
67
59-62
2011
Paraburkholderia xenovorans, Paraburkholderia xenovorans (P37333), Paraburkholderia xenovorans (P37334)
brenda
Kumar, P.; Mohammadi, M.; Viger, J.F.; Barriault, D.; Gomez-Gil, L.; Eltis, L.D.; Bolin, J.T.; Sylvestre, M.
Structural insight into the expanded PCB-degrading abilities of a biphenyl dioxygenase obtained by directed evolution
J. Mol. Biol.
405
531-547
2011
Paraburkholderia xenovorans
brenda