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(1S)-indanol + NADH + O2
(1S)-indanol + trans-1,3-indandiol
-
recombinant enzyme
85.5% indanol, 11.5% 1,3-indandiol, minor products: (1S)-indenol and 1-indanone
?
(2S)-flavanone + NADH + H+ + O2
8-hydroxy-(2S)-flavanone + NAD+ + ?
(3S)-isoflavanone + NADH + H+ + O2
8-hydroxy-(3S)-isoflavanone + NAD+ + ?
(R)-1-indanol + NADH + H+ + O2
cis-1,3-indandiol + (R)-3-hydroxy-1-indanone + cis-1,2,3-indantriol + NAD+
-
activity in E. coli cells expressing recombinant naphthalene dioxygenase
71% cis-1,3-indandiol, 18.2% (R)-3-hydroxy-1-indanone and 10.8% cis-1,2,3-indantriol
?
(S)-1-indanol + NADH + H+ + O2
trans-(1S,3S)-indan-1,3-diol + (R)-3-hydroxy-1-indanone + NAD+
-
activity in E. coli cells expressing recombinant naphthalene dioxygenase
95.5% trans-(1S,3S)-indan-1,3-diol
?
(S)-1-indenol + NADH + O2
syn-2,3-dihydroxy-1-indanol + anti-2,3-dihydroxy-1-indanol
-
recombinant enzyme system
-
?
1,2,4-trimethylnaphthalene + NADH + H+ + O2
? + NAD+
1,2,5-trimethylnaphthalene + NADH + H+ + O2
? + NAD+
1,2-dihydronaphthalene + NADH + O2
cis-(1R,2S)-dihydroxy-1,2,3,4-tetrahydronaphthalene + cis-(1R,2S)-dihydroxy-1,2-dihydronaphthalene + NAD+
-
naphthalene dioxygenase activity in cells induced by salicylate
-
?
1,3-benzodithiole + NADH + O2
(R)-1,3-benzodithiole-1-oxide + NAD+
1,4-benzo[d]dithiine + NADH + O2
(S)-1,4-benzo[d]dithiin-1-oxide + NAD+
1,4-dimethylnaphthalene + NADH + H+ + O2
? + NAD+
1,5-dimethylnaphthalene + NADH + H+ + O2
? + NAD+
1-chloronaphthalene + NADH + H+ + O2
(1R,2S)-5-chloro-1,2-dihydronaphthalene-1,2-diol + (1S,2R)-8-chloro-1,2-dihydronaphthalene-1,2-diol + NAD+
1-methylnaphthalene + NADH + H+ + O2
? + NAD+
-
-
generation of dioxygenated product, but mainly formation of side-chain monooxygenated product
-
?
2,3-dihydro-1,4-benzo[d]dithiine + NADH + O2
(S)-2,3-dihydrobenzo[d]dithiin-1-oxide + NAD+
2,3-dimethylnaphthalene + NADH + H+ + O2
? + NAD+
-
-
generation of mono- and mostly dioxygenated products
-
?
2,4,6-trimethylnaphthalene + NADH + H+ + O2
? + NAD+
-
-
generation of mostly mono- and some dioxygenated products
-
?
2-chlorobiphenyl + NADH + O2
2-chloro-2',3'-dihydrobiphenyl-2',3'-diol + NAD+
2-chlorophenol + NADH + O2
chlorohydroquinone + NAD+
2-methoxynaphthalene + NADH + O2
(1R,2S)-dihydroxy-7-methoxy-1,2-dihydronaphthalene + NAD+
-
naphtalene dioxygenase activity in whole cells and activity in E. coli cells expressing naphtalene dioxygenase
minor product (1R,2S)-dihydroxy-6-methoxy-1,2-dihydronaphthalene
?
2-methyl-1,3-benzodithiole + NADH + O2
(1S,2R)-2-methyl-1,3-benzodithiole-1-oxide + (1S,2S)-2-methyl-1,3-benzodithiole-1-oxide + NAD+
2-methylnaphthalene + NADH + H+ + O2
? + NAD+
-
-
generation of two different dioxygenated products
-
?
2-methylquinoline + NADH + H+ + O2
(5R,6S)-2-methyl-5,6-dihydroquinoline-5,6-diol + 2-methylquinolin-8-ol + NAD+
3 benz[a]anthracene + 3 NADH + 3 O2 + 3 H+
benz[a]anthracene-10,11-cis-dihydrodiol + benz[a]anthracene-8,9-cis-dihydrodiol + benz[a]anthracene-1,2-cis-dihydrodiol + 3 NAD+
-
-
-
-
?
3,4-dihydro-2H-1lambda4,5-benzodithiepin + NADH + O2
(S)-1,2,3,4-tetrahydro-1lambda4,5-benzodithiepin-1-oxide + NAD+
3-chlorobiphenyl + NADH + O2
3-chloro-2',3'-dihydrobiphenyl-2',3'-diol + NAD+
3-chlorophenol + NADH + O2
chlorohydroquinone + 4-chlorocatechol + NAD+
3-methylisoquinoline + NADH + H+ + O2
cis-3-methyl-7,8-dihydroisoquinoline-7,8-diol + 3-methylisoquinolin-5-ol + NAD+
3-nitrotoluene + NADH + O2
4-nitrobenzyl alcohol + NAD+
4-chlorobiphenyl + NADH + O2
4-chloro-2',3'-dihydrobiphenyl-2',3'-diol + NAD+
4-chlorophenol + NADH + O2
4-chlorocatechol + NAD+
6,7-dihydro-5H-benzocycloheptene + NADH + O2
(1R,2S)-cis-dihydroxybenzocycloheptane + NAD+
-
naphthalene dioxygenase activity in cells induced by salicylate
enantiomeric excess greater than 98%
?
8-methylquinoline + NADH + H+ + O2
5,6-dihydroquinolin-8-ylmethanol + (5R,6S)-8-methyl-5,6-dihydroquinoline-5,6-diol + NAD+
9,10-dihydroanthracene + NADH + O2
cis-(1R,2S)-1,2-dihydroxy-1,2,9,10-tetrahydroanthracene + NAD+
-
naphthalene dioxygenase activity in cells induced by salicylate
more than 95% yield, enantiomeric excess greater than 95%, minor product: 9-hydroxy-9,10-dihydroanthracene
?
9,10-dihydrophenanthrene + NADH + O2
cis-(3S,4R)-3,4-dihydroxy-3,4,9,10-tetrahydrophenanthrene + (S)-9-hydroxy-9,10-dihydrophenanthrene
-
naphthalene dioxygenase activity in cells induced by salicylate
70% cis-(3S,4R)-3,4-dihydroxy-3,4,9,10-tetrahydrophenanthrene, enantiomeric excess greater than 95%, 30% (S)-9-hydroxy-9,10-dihydrophenanthrene
?
acenaphthene + NADH + H+ + O2
?
-
-
-
?
acenaphthylene + NADH + H+ + O2
?
-
-
-
?
anthanthrene + NADH + H+ + O2
?
-
-
-
?
anthracene + NADH + H+ + O2
?
-
-
-
?
anthracene + NADH + O2
(1R,2S)-1,2-dihydroanthracene-1,2-diol + (1S,2R)-1,2-dihydroanthracene-1,2-diol + NAD+
benzamide + NADH + H+ + O2
?
benzene + NADH + O2
H2O2 + cis-benzene-1,2-dihydrodiol + NAD+
-
40-50% of O2 is reduced to H2O2 by an uncoupling reaction, only trace amounts of cis-benzene-1,2-dihydrodiol are formed
-
?
benzocyclobutene + NADH + O2
benzocyclobutene-1-ol + benzocyclobutene-1-one
-
naphtalene dioxygenase activity in intact cells
-
?
benzo[a]coronene + NADH + H+ + O2
?
-
-
-
?
benzo[a]naphthacene + NADH + H+ + O2
?
-
-
-
?
benzo[a]pyrene + NADH + H+ + O2
?
-
-
-
?
benzo[a]pyrene + NADH + H+ + O2
cis-9,10-dihydroxy-9,10-dihydrobenzo[a]pyrene + NAD+
-
-
-
-
?
benzo[b]chrysene + NADH + H+ + O2
?
-
-
-
?
benzo[b]fluorene + NADH + H+ + O2
?
-
-
-
?
benzo[c]chrysene + NADH + H+ + O2
?
-
-
-
?
benzo[c]phenanthrene + NADH + H+ + O2
?
-
-
-
?
benzo[e]pyrene + NADH + H+ + O2
?
-
-
-
?
benzo[ghi]fluoranthene + NADH + H+ + O2
?
-
-
-
?
benzo[ghi]naphtho[cde]perylene + NADH + H+ + O2
?
-
-
-
?
benzo[ghi]perylene + NADH + H+ + O2
?
-
-
-
?
benzo[j]fluoranthene + NADH + H+ + O2
?
-
-
-
?
benzo[rst]dinaphtho[defg,ijkl]pentaphene + NADH + H+ + O2
?
-
-
-
?
benzo[rst]phenanthro[1,10,9-cde]pentaphene + NADH + H+ + O2
?
-
-
-
?
benzpyrene + NADH + H+ + O2
?
benz[a]anthracene + NADH + H+ + O2
?
-
-
-
?
benz[a]anthracene + NADH + H+ + O2
cis,cis-1,2,10,11-tetrahydroxy-1,2,10,11-tetrahydrobenz[a]anthracene + NAD+
-
-
-
-
?
benz[a]anthracene-1,2-cis-dihydrodiol + NADH + O2
benz[a]anthracene-1,2,10,11-bis-cis-dihydrodiol + NAD+
-
-
-
-
?
benz[a]anthracene-10,11-cis-dihydrodiol + NADH + O2
benz[a]anthracene-1,2,10,11-bis-cis-dihydrodiol + NAD+
-
-
-
-
?
benz[e]acephenanthrylene + NADH + H+ + O2
?
-
-
-
?
benz[rst]anthra[cde]pentaphene + NADH + H+ + O2
?
-
-
-
?
biphenyl + NADH + O2
? + NAD+
chrysene + NADH + H+ + O2
?
-
-
-
?
chrysene + NADH + H+ + O2
cis-3,4-dihydroxy-3,4-dihydrochrysene + NAD+
-
-
-
-
?
chrysene + NADH + O2
chrysene-3,4-cis-dihydrodiol + chrysene-3,4,9,10-bis-cis-dihydrodiol + NAD+
-
-
-
-
?
coronene + NADH + H+ + O2
?
-
-
-
?
dibenzofuran + NADH + H+ + O2
1,2-dihydroxydibenzofuran + NAD+
-
-
-
-
?
dibenzofuran + NADH + O2
(1R,2S)-cis-1,2-dihydroxy-1,2-dihydrodibenzofuran + (3S,4R)-cis-3,4-dihydroxy-3,4-dihydrodibenzofuran + NAD+
-
naphthalene dioxygenase activity in cells induced by salicylate
-
-
?
dibenzothiophene + NADH + H+ + O2
1,2-dihydroxydibenzothiophene + NAD+
-
-
-
-
?
dibenzothiophene + NADH + O2
(1R,2S)-cis-1,2-dihydroxy-dihydrodibenzothiophene + dibenzothiophene sulfoxide
-
naphthalene dioxygenase activity in cells induced by salicylate
84-87% (1R,2S)-cis-1,2-dihydroxy-dihydrodibenzothiophene, enantiomeric excess greater than 95%, 15% dibenzothiophene sulfoxide
?
dibenzo[b,def]chrysene + NADH + H+ + O2
?
-
-
-
?
dibenzo[bc,ef]coronene + NADH + H+ + O2
?
-
-
-
?
dibenzo[g,p]chrysene + NADH + H+ + O2
?
-
-
-
?
dibenzo[j,lm]naphtho[ab]perylene + NADH + H+ + O2
?
-
-
-
?
dibenz[a,c]anthracene + NADH + H+ + O2
?
-
-
-
?
dibenz[a,h]anthracene + NADH + H+ + O2
?
-
-
-
?
dibenz[a,j]anthracene + NADH + H+ + O2
?
-
-
-
?
dinaphtho[defg,opqr]pentacene + NADH + H+ + O2
?
-
-
-
?
ethylbenzene + NADH + H+ + O2
(S)-1-phenylethanol + (R)-1-phenylethanol + NAD+
ethylphenyl sulfide + NADH + H+ + O2
(R)-ethylphenyl sulfoxide + NAD+
fluoranthene + NADH + H+ + O2
?
-
-
-
?
fluoranthene + NADH + H+ + O2
cis-7,8-dihydroxy-7,8-dihydrofluoranthene + cis-2,3-dihydroxy-2,3-dihydrofluoranthene + NAD+
-
-
-
-
?
fluorene + NADH + O2
(3S,4R)-cis-3,4dihydroxy-3,4-dihydrofluorene + 9-fluorenol + NAD+
-
naphthalene dioxygenase activity in cells induced by salicylate
-
-
?
fluorine + NADH + H+ + O2
?
-
-
-
?
fulvic acid + NADH + H+ + O2
?
hexabenzo[a,cd,f,j,lm,o]perylene + NADH + H+ + O2
?
-
-
-
?
humic acid + NADH + H+ + O2
?
indan + NADH + H+ + O2
(1S)-indenol + (1S)-indanol + NAD+
-
recombinant enzyme, enantiospecific monooxygenation
20% indenol, 67.1% indanol, minor products: indene, 1-indanone and (1R,2S)-indandiol
?
indan + NADH + H+ + O2
(S)-1-indanol + (R)-1-indanol + NAD+
-
-
-
?
indan + NADH + H+ + O2
1-indanol + NAD+
-
-
-
?
indene + NADH + H+ + O2
(S)-1-indenol + (R)-1-indenol + NAD+
-
-
-
?
indene + NADH + O2
(1S)-indenol + (1R,2S)-indandiol + NAD+
-
recombinant enzyme
57.9% indenol, 29.6% indandiol
?
indole + ?
2,3-dihydroxy-2,3-dihydroindole + ?
indole + ? + O2
cis-indole-2,3-dihydrodiol
indole + NADH + H+ + O2
?
indole + NADH + H+ + O2
cis-indole-2,3-dihydrodiol + NAD+
-
-
-
?
indole + NADH + O2
(2S,3S)-2,3-dihydro-1H-indole-2,3-diol + NAD+
indole-3-acetate + NADH + H+ + O2
?
-
-
-
?
m-cresol + NADH + O2
methylhydroquinone + 3-methylcatechol + 4-methylcatechol + NAD+
naphthacene + NADH + H+ + O2
?
-
-
-
?
naphthalene + NAD(P)H + O2
cis-(1R,2S)-1,2-dihydronaphthalene-1,2-diol + NAD(P)+
naphthalene + NADH + H+ + O2
(1R,2S)-1,2-dihydronaphthalene-1,2-diol + NAD+
naphthalene + NADH + H+ + O2
1,2-dihydronaphthalene-1,2-diol + NAD+
naphthalene + NADH + O2
(1R,2S)-1,2-dihydronaphthalene-1,2-diol + NAD+
naphthalene + NADH + O2
cis-(1R,2S)-1,2-dihydronaphthalene-1,2-diol + NAD+
naphtho[a]anthracene + NADH + H+ + O2
?
-
-
-
?
naphtho[bcd]perylene + NADH + H+ + O2
?
-
-
-
?
naphtho[d]coronene + NADH + H+ + O2
?
-
-
-
?
o-cresol + NADH + O2
methylhydroquinone + 3-methylcatechol + NAD+
-
-
-
-
?
p-cresol + NADH + O2
4-methylcatechol + NAD+
-
-
-
-
?
pentabenzo[a,cd,f,j,lm]perylene + NADH + H+ + O2
?
-
-
-
?
pentacene + NADH + H+ + O2
?
-
-
-
?
pentaphene + NADH + H+ + O2
?
-
-
-
?
perylene + NADH + H+ + O2
?
-
-
-
?
phenanthrene + NADH + H+ + O2
?
phenanthrene + NADH + O2
(1R,2S)-1,2-dihydrophenanthrene-1,2-diol + (1S,2R)-1,2-dihydrophenanthrene-1,2-diol + (3R,4S)-3,4-dihydrophenanthrene-3,4-diol + (3S,4R)-3,4-dihydrophenanthrene-3,4-diol + NAD+
phenanthrene + NADH + O2
? + NAD+
-
-
-
-
?
phenanthro[3,4-c]phenanthrene + NADH + H+ + O2
?
-
-
-
?
phenetole + NADH + H+ + O2
phenol + vinyloxybenzene + (S)-ethylphenyl sulfoxide + NAD+
-
-
-
?
phenol + NADH + O2
catechol + hydroquinone + NAD+
-
-
-
-
?
picene + NADH + H+ + O2
?
-
-
-
?
pyranthrene + NADH + H+ + O2
?
-
-
-
?
pyrene + NADH + H+ + O2
?
-
-
-
?
pyrene + NADH + H+ + O2
pyrene cis-4,5-dihydrodiol + NAD+
quinazoline + NADH + H+ + O2
(5R,6S)-5,6-dihydroquinazoline-5,6-diol + quinazolin-8-ol
quinoline + NADH + H+ + O2
(5R,6S)-5,6-dihydroquinoline-5,6-diol + quinolin-3-ol + NAD+
quinoxaline + NADH + H+ + O2
(5R,6S)-5,6-dihydroquinoxaline-5,6-diol + NAD+
-
-
exclusive product
-
?
styrene + NADH + H+ + O2
(R)-1-phenylethane-1,2-diol + (S)-1-phenylethane-1,2-diol + NAD+
-
-
-
?
styrene + NADH + O2
(R)-1-phenyl-1,2-ethanediol + NAD+
-
recombinant enzyme system
78.6% enantiomeric excess
?
tetrabenzo[a,cd,f,lm]perylene + NADH + H+ + O2
?
-
-
-
?
thioanisole + NADH + H+ + O2
methyl phenyl sulfoxide + NAD+
-
-
-
?
triphenylene + NADH + H+ + O2
?
-
-
-
?
additional information
?
-
(2S)-flavanone + NADH + H+ + O2
8-hydroxy-(2S)-flavanone + NAD+ + ?
-
no substrate for wild-type, substrate for mutants F224C, F224K, F224Q, F224Y
product has an oxygen atom directly attached to the aromatic ring. Upon completion of the dihydroxylation, the oxygen atom on the C-ring is believed to expel the 7-OH group through donation of its lone pair electrons and the charged intermediate. Once formed this readily re-aromatizes to provide 8-hydroxyflavanones or 8-hydroxyisoflavanones
-
?
(2S)-flavanone + NADH + H+ + O2
8-hydroxy-(2S)-flavanone + NAD+ + ?
-
no substrate for wild-type, substrate for mutants F224C, F224K, F224Q, F224Y
product has an oxygen atom directly attached to the aromatic ring. Upon completion of the dihydroxylation, the oxygen atom on the C-ring is believed to expel the 7-OH group through donation of its lone pair electrons and the charged intermediate. Once formed this readily re-aromatizes to provide 8-hydroxyflavanones or 8-hydroxyisoflavanones
-
?
(3S)-isoflavanone + NADH + H+ + O2
8-hydroxy-(3S)-isoflavanone + NAD+ + ?
-
no substrate for wild-type, substrate for mutants F224K, F224Y
product has an oxygen atom directly attached to the aromatic ring. Upon completion of the dihydroxylation, the oxygen atom on the C-ring is believed to expel the 7-OH group through donation of its lone pair electrons and the charged intermediate. Once formed this readily re-aromatizes to provide 8-hydroxyflavanones or 8-hydroxyisoflavanones
-
?
(3S)-isoflavanone + NADH + H+ + O2
8-hydroxy-(3S)-isoflavanone + NAD+ + ?
-
no substrate for wild-type, substrate for mutants F224K, F224Y
product has an oxygen atom directly attached to the aromatic ring. Upon completion of the dihydroxylation, the oxygen atom on the C-ring is believed to expel the 7-OH group through donation of its lone pair electrons and the charged intermediate. Once formed this readily re-aromatizes to provide 8-hydroxyflavanones or 8-hydroxyisoflavanones
-
?
1,2,4-trimethylnaphthalene + NADH + H+ + O2
? + NAD+
-
-
generation of mono- and dioxygenated products
-
?
1,2,4-trimethylnaphthalene + NADH + H+ + O2
? + NAD+
-
-
generation of mono- and dioxygenated products
-
?
1,2,5-trimethylnaphthalene + NADH + H+ + O2
? + NAD+
-
-
generation of mostly mono- and some dioxygenated products
-
?
1,2,5-trimethylnaphthalene + NADH + H+ + O2
? + NAD+
-
-
generation of mostly mono- and some dioxygenated products
-
?
1,3-benzodithiole + NADH + O2
(R)-1,3-benzodithiole-1-oxide + NAD+
-
-
-
-
?
1,3-benzodithiole + NADH + O2
(R)-1,3-benzodithiole-1-oxide + NAD+
-
-
-
-
?
1,4-benzo[d]dithiine + NADH + O2
(S)-1,4-benzo[d]dithiin-1-oxide + NAD+
-
-
-
-
?
1,4-benzo[d]dithiine + NADH + O2
(S)-1,4-benzo[d]dithiin-1-oxide + NAD+
-
-
-
-
?
1,4-dimethylnaphthalene + NADH + H+ + O2
? + NAD+
-
-
generation of monooxygenated products
-
?
1,4-dimethylnaphthalene + NADH + H+ + O2
? + NAD+
-
-
generation of monooxygenated products
-
?
1,5-dimethylnaphthalene + NADH + H+ + O2
? + NAD+
-
-
generation of monooxygenated products
-
?
1,5-dimethylnaphthalene + NADH + H+ + O2
? + NAD+
-
-
generation of monooxygenated products
-
?
1-chloronaphthalene + NADH + H+ + O2
(1R,2S)-5-chloro-1,2-dihydronaphthalene-1,2-diol + (1S,2R)-8-chloro-1,2-dihydronaphthalene-1,2-diol + NAD+
-
-
-
?
1-chloronaphthalene + NADH + H+ + O2
(1R,2S)-5-chloro-1,2-dihydronaphthalene-1,2-diol + (1S,2R)-8-chloro-1,2-dihydronaphthalene-1,2-diol + NAD+
-
-
-
?
2,3-dihydro-1,4-benzo[d]dithiine + NADH + O2
(S)-2,3-dihydrobenzo[d]dithiin-1-oxide + NAD+
-
-
-
-
?
2,3-dihydro-1,4-benzo[d]dithiine + NADH + O2
(S)-2,3-dihydrobenzo[d]dithiin-1-oxide + NAD+
-
-
-
-
?
2-chlorobiphenyl + NADH + O2
2-chloro-2',3'-dihydrobiphenyl-2',3'-diol + NAD+
-
recombinant histidine-tagged terminal dioxygenase
-
?
2-chlorobiphenyl + NADH + O2
2-chloro-2',3'-dihydrobiphenyl-2',3'-diol + NAD+
-
recombinant histidine-tagged terminal dioxygenase
-
?
2-chlorophenol + NADH + O2
chlorohydroquinone + NAD+
-
-
-
-
?
2-chlorophenol + NADH + O2
chlorohydroquinone + NAD+
-
-
-
-
?
2-methyl-1,3-benzodithiole + NADH + O2
(1S,2R)-2-methyl-1,3-benzodithiole-1-oxide + (1S,2S)-2-methyl-1,3-benzodithiole-1-oxide + NAD+
-
-
cis and trans product
-
?
2-methyl-1,3-benzodithiole + NADH + O2
(1S,2R)-2-methyl-1,3-benzodithiole-1-oxide + (1S,2S)-2-methyl-1,3-benzodithiole-1-oxide + NAD+
-
-
cis and trans product
-
?
2-methylquinoline + NADH + H+ + O2
(5R,6S)-2-methyl-5,6-dihydroquinoline-5,6-diol + 2-methylquinolin-8-ol + NAD+
-
-
99% total conversion, giving 92% (5R,6S)-2-methyl-5,6-dihydroquinoline-5,6-diol and 8% 2-methylquinolin-8-ol
-
?
2-methylquinoline + NADH + H+ + O2
(5R,6S)-2-methyl-5,6-dihydroquinoline-5,6-diol + 2-methylquinolin-8-ol + NAD+
-
-
99% total conversion, giving 92% (5R,6S)-2-methyl-5,6-dihydroquinoline-5,6-diol and 8% 2-methylquinolin-8-ol
-
?
3,4-dihydro-2H-1lambda4,5-benzodithiepin + NADH + O2
(S)-1,2,3,4-tetrahydro-1lambda4,5-benzodithiepin-1-oxide + NAD+
-
-
-
-
?
3,4-dihydro-2H-1lambda4,5-benzodithiepin + NADH + O2
(S)-1,2,3,4-tetrahydro-1lambda4,5-benzodithiepin-1-oxide + NAD+
-
-
-
-
?
3-chlorobiphenyl + NADH + O2
3-chloro-2',3'-dihydrobiphenyl-2',3'-diol + NAD+
-
recombinant histidine-tagged terminal dioxygenase
-
?
3-chlorobiphenyl + NADH + O2
3-chloro-2',3'-dihydrobiphenyl-2',3'-diol + NAD+
-
recombinant histidine-tagged terminal dioxygenase
-
?
3-chlorophenol + NADH + O2
chlorohydroquinone + 4-chlorocatechol + NAD+
-
-
-
-
?
3-chlorophenol + NADH + O2
chlorohydroquinone + 4-chlorocatechol + NAD+
-
-
-
-
?
3-methylisoquinoline + NADH + H+ + O2
cis-3-methyl-7,8-dihydroisoquinoline-7,8-diol + 3-methylisoquinolin-5-ol + NAD+
-
-
99% total conversion, giving 73% cis-3-methyl-7,8-dihydroisoquinoline-7,8-diol + 27% 3-methylisoquinolin-5-ol
-
?
3-methylisoquinoline + NADH + H+ + O2
cis-3-methyl-7,8-dihydroisoquinoline-7,8-diol + 3-methylisoquinolin-5-ol + NAD+
-
-
99% total conversion, giving 73% cis-3-methyl-7,8-dihydroisoquinoline-7,8-diol + 27% 3-methylisoquinolin-5-ol
-
?
3-nitrotoluene + NADH + O2
4-nitrobenzyl alcohol + NAD+
-
-
-
-
?
3-nitrotoluene + NADH + O2
4-nitrobenzyl alcohol + NAD+
-
-
-
-
?
4-chlorobiphenyl + NADH + O2
4-chloro-2',3'-dihydrobiphenyl-2',3'-diol + NAD+
-
recombinant histidine-tagged terminal dioxygenase
-
?
4-chlorobiphenyl + NADH + O2
4-chloro-2',3'-dihydrobiphenyl-2',3'-diol + NAD+
-
recombinant histidine-tagged terminal dioxygenase
-
?
4-chlorophenol + NADH + O2
4-chlorocatechol + NAD+
-
-
-
-
?
4-chlorophenol + NADH + O2
4-chlorocatechol + NAD+
-
-
-
-
?
8-methylquinoline + NADH + H+ + O2
5,6-dihydroquinolin-8-ylmethanol + (5R,6S)-8-methyl-5,6-dihydroquinoline-5,6-diol + NAD+
-
-
78% total conversion, giving 72% 5,6-dihydroquinolin-8-ylmethanol + 28% (5R,6S)-8-methyl-5,6-dihydroquinoline-5,6-diol
-
?
8-methylquinoline + NADH + H+ + O2
5,6-dihydroquinolin-8-ylmethanol + (5R,6S)-8-methyl-5,6-dihydroquinoline-5,6-diol + NAD+
-
-
78% total conversion, giving 72% 5,6-dihydroquinolin-8-ylmethanol + 28% (5R,6S)-8-methyl-5,6-dihydroquinoline-5,6-diol
-
?
anthracene + NADH + O2
(1R,2S)-1,2-dihydroanthracene-1,2-diol + (1S,2R)-1,2-dihydroanthracene-1,2-diol + NAD+
-
-
-
-
?
anthracene + NADH + O2
(1R,2S)-1,2-dihydroanthracene-1,2-diol + (1S,2R)-1,2-dihydroanthracene-1,2-diol + NAD+
-
-
-
-
?
benzamide + NADH + H+ + O2
?
-
-
-
?
benzamide + NADH + H+ + O2
?
-
-
-
?
benzpyrene + NADH + H+ + O2
?
-
-
-
-
?
benzpyrene + NADH + H+ + O2
?
-
-
-
-
?
biphenyl + NADH + O2
? + NAD+
-
-
-
-
?
biphenyl + NADH + O2
? + NAD+
-
-
-
-
?
biphenyl + NADH + O2
? + NAD+
-
-
-
-
?
ethylbenzene + NADH + H+ + O2
(S)-1-phenylethanol + (R)-1-phenylethanol + NAD+
-
-
-
?
ethylbenzene + NADH + H+ + O2
(S)-1-phenylethanol + (R)-1-phenylethanol + NAD+
-
-
-
?
ethylphenyl sulfide + NADH + H+ + O2
(R)-ethylphenyl sulfoxide + NAD+
-
-
-
?
ethylphenyl sulfide + NADH + H+ + O2
(R)-ethylphenyl sulfoxide + NAD+
-
-
-
?
fulvic acid + NADH + H+ + O2
?
-
-
-
-
?
fulvic acid + NADH + H+ + O2
?
-
-
-
-
?
humic acid + NADH + H+ + O2
?
-
-
-
-
?
humic acid + NADH + H+ + O2
?
-
-
-
-
?
indole + ?
2,3-dihydroxy-2,3-dihydroindole + ?
-
-
-
-
?
indole + ?
2,3-dihydroxy-2,3-dihydroindole + ?
-
-
-
-
?
indole + ? + O2
cis-indole-2,3-dihydrodiol
-
reaction of recombinant E. coli transformed with Pseudomonas sp. DNA
-
?
indole + ? + O2
cis-indole-2,3-dihydrodiol
-
reaction of recombinant E. coli transformed with Pseudomonas sp. DNA
-
?
indole + NADH + H+ + O2
?
-
-
-
-
?
indole + NADH + H+ + O2
?
-
-
-
-
?
indole + NADH + O2
(2S,3S)-2,3-dihydro-1H-indole-2,3-diol + NAD+
-
-
-
-
?
indole + NADH + O2
(2S,3S)-2,3-dihydro-1H-indole-2,3-diol + NAD+
-
-
-
-
?
indole + NADH + O2
(2S,3S)-2,3-dihydro-1H-indole-2,3-diol + NAD+
-
-
-
-
?
indole + NADH + O2
(2S,3S)-2,3-dihydro-1H-indole-2,3-diol + NAD+
-
-
-
-
?
m-cresol + NADH + O2
methylhydroquinone + 3-methylcatechol + 4-methylcatechol + NAD+
-
-
-
-
?
m-cresol + NADH + O2
methylhydroquinone + 3-methylcatechol + 4-methylcatechol + NAD+
-
-
-
-
?
naphthalene + NAD(P)H + O2
cis-(1R,2S)-1,2-dihydronaphthalene-1,2-diol + NAD(P)+
-
-
only cis-isomer by bacteria, product rapidly autooxidizes to 1,2-naphthoquinone
?
naphthalene + NAD(P)H + O2
cis-(1R,2S)-1,2-dihydronaphthalene-1,2-diol + NAD(P)+
-
-
only cis-isomer by bacteria, product rapidly autooxidizes to 1,2-naphthoquinone
?
naphthalene + NAD(P)H + O2
cis-(1R,2S)-1,2-dihydronaphthalene-1,2-diol + NAD(P)+
-
-
-
-
?
naphthalene + NAD(P)H + O2
cis-(1R,2S)-1,2-dihydronaphthalene-1,2-diol + NAD(P)+
-
50% activity with NADH compared to NADPH
-
-
?
naphthalene + NAD(P)H + O2
cis-(1R,2S)-1,2-dihydronaphthalene-1,2-diol + NAD(P)+
-
-
-
-
?
naphthalene + NAD(P)H + O2
cis-(1R,2S)-1,2-dihydronaphthalene-1,2-diol + NAD(P)+
-
-
-
?
naphthalene + NAD(P)H + O2
cis-(1R,2S)-1,2-dihydronaphthalene-1,2-diol + NAD(P)+
-
-
-
?
naphthalene + NADH + H+ + O2
(1R,2S)-1,2-dihydronaphthalene-1,2-diol + NAD+
-
-
-
-
?
naphthalene + NADH + H+ + O2
(1R,2S)-1,2-dihydronaphthalene-1,2-diol + NAD+
-
-
-
?
naphthalene + NADH + H+ + O2
(1R,2S)-1,2-dihydronaphthalene-1,2-diol + NAD+
-
-
-
-
?
naphthalene + NADH + H+ + O2
(1R,2S)-1,2-dihydronaphthalene-1,2-diol + NAD+
-
-
-
?
naphthalene + NADH + H+ + O2
(1R,2S)-1,2-dihydronaphthalene-1,2-diol + NAD+
-
-
-
?
naphthalene + NADH + H+ + O2
(1R,2S)-1,2-dihydronaphthalene-1,2-diol + NAD+
-
-
-
-
?
naphthalene + NADH + H+ + O2
(1R,2S)-1,2-dihydronaphthalene-1,2-diol + NAD+
-
-
-
-
?
naphthalene + NADH + H+ + O2
(1R,2S)-1,2-dihydronaphthalene-1,2-diol + NAD+
-
-
-
?
naphthalene + NADH + H+ + O2
(1R,2S)-1,2-dihydronaphthalene-1,2-diol + NAD+
-
the catalytic ferrous site is primed for the O2 reaction when substrate is bound in the active site in the presence of the reduced Rieske site. These structural changes ensure that two electrons and the substrate are present before the binding and activation of O2, which avoids the uncontrolled formation and release of reactive oxygen species
-
-
?
naphthalene + NADH + H+ + O2
(1R,2S)-1,2-dihydronaphthalene-1,2-diol + NAD+
-
-
-
?
naphthalene + NADH + H+ + O2
(1R,2S)-1,2-dihydronaphthalene-1,2-diol + NAD+
-
-
-
-
?
naphthalene + NADH + H+ + O2
(1R,2S)-1,2-dihydronaphthalene-1,2-diol + NAD+
-
-
exclusive product
-
?
naphthalene + NADH + H+ + O2
(1R,2S)-1,2-dihydronaphthalene-1,2-diol + NAD+
-
-
exclusive product
-
?
naphthalene + NADH + H+ + O2
(1R,2S)-1,2-dihydronaphthalene-1,2-diol + NAD+
-
-
-
-
?
naphthalene + NADH + H+ + O2
1,2-dihydronaphthalene-1,2-diol + NAD+
-
-
-
-
?
naphthalene + NADH + H+ + O2
1,2-dihydronaphthalene-1,2-diol + NAD+
-
-
-
-
?
naphthalene + NADH + O2
(1R,2S)-1,2-dihydronaphthalene-1,2-diol + NAD+
-
initial oxidative reaction in bacterial naphthalene catabolism
-
?
naphthalene + NADH + O2
(1R,2S)-1,2-dihydronaphthalene-1,2-diol + NAD+
-
initial oxidative reaction in bacterial naphthalene catabolism
-
?
naphthalene + NADH + O2
(1R,2S)-1,2-dihydronaphthalene-1,2-diol + NAD+
-
-
-
?
naphthalene + NADH + O2
(1R,2S)-1,2-dihydronaphthalene-1,2-diol + NAD+
-
-
-
?
naphthalene + NADH + O2
(1R,2S)-1,2-dihydronaphthalene-1,2-diol + NAD+
-
-
-
-
?
naphthalene + NADH + O2
(1R,2S)-1,2-dihydronaphthalene-1,2-diol + NAD+
-
initial oxidative reaction in bacterial naphthalene catabolism
-
?
naphthalene + NADH + O2
(1R,2S)-1,2-dihydronaphthalene-1,2-diol + NAD+
-
three-component dioxygenase, uses two proteins containing three redox centers to transfer electrons to the terminal oxygenase
-
?
naphthalene + NADH + O2
(1R,2S)-1,2-dihydronaphthalene-1,2-diol + NAD+
-
genes coding for naphthalene dioxygenase: ndoA, ndoB and ndoC
-
?
naphthalene + NADH + O2
(1R,2S)-1,2-dihydronaphthalene-1,2-diol + NAD+
-
-
-
?
naphthalene + NADH + O2
(1R,2S)-1,2-dihydronaphthalene-1,2-diol + NAD+
-
-
-
-
?
naphthalene + NADH + O2
(1R,2S)-1,2-dihydronaphthalene-1,2-diol + NAD+
-
-
-
-
?
naphthalene + NADH + O2
(1R,2S)-1,2-dihydronaphthalene-1,2-diol + NAD+
-
-
-
-
?
naphthalene + NADH + O2
(1R,2S)-1,2-dihydronaphthalene-1,2-diol + NAD+
-
-
-
-
?
naphthalene + NADH + O2
cis-(1R,2S)-1,2-dihydronaphthalene-1,2-diol + NAD+
-
-
-
?
naphthalene + NADH + O2
cis-(1R,2S)-1,2-dihydronaphthalene-1,2-diol + NAD+
-
-
-
?
naphthalene + NADH + O2
cis-(1R,2S)-1,2-dihydronaphthalene-1,2-diol + NAD+
-
-
-
?
naphthalene + NADH + O2
cis-(1R,2S)-1,2-dihydronaphthalene-1,2-diol + NAD+
-
-
-
?
naphthalene + NADH + O2
cis-(1R,2S)-1,2-dihydronaphthalene-1,2-diol + NAD+
-
-
-
?
naphthalene + NADH + O2
cis-(1R,2S)-1,2-dihydronaphthalene-1,2-diol + NAD+
-
-
-
?
naphthalene + NADH + O2
cis-(1R,2S)-1,2-dihydronaphthalene-1,2-diol + NAD+
-
3 component enzyme system consisting of ferredoxinNAP reductase, ferredoxinNAP and oxygenase ISPNAP, ferredoxinNAP reductase reduces: 2,6-dichlorophenolindophenol, ferricyanide, nitro blue tetrazolium and cytochrome c, in the presence of FAD ferredoxinNAP reductase transfers electrons to ferredoxin
-
?
naphthalene + NADH + O2
cis-(1R,2S)-1,2-dihydronaphthalene-1,2-diol + NAD+
-
-
-
?
phenanthrene + NADH + H+ + O2
?
-
-
-
-
?
phenanthrene + NADH + H+ + O2
?
-
-
-
?
phenanthrene + NADH + O2
(1R,2S)-1,2-dihydrophenanthrene-1,2-diol + (1S,2R)-1,2-dihydrophenanthrene-1,2-diol + (3R,4S)-3,4-dihydrophenanthrene-3,4-diol + (3S,4R)-3,4-dihydrophenanthrene-3,4-diol + NAD+
-
-
-
-
?
phenanthrene + NADH + O2
(1R,2S)-1,2-dihydrophenanthrene-1,2-diol + (1S,2R)-1,2-dihydrophenanthrene-1,2-diol + (3R,4S)-3,4-dihydrophenanthrene-3,4-diol + (3S,4R)-3,4-dihydrophenanthrene-3,4-diol + NAD+
-
-
-
-
?
pyrene + NADH + H+ + O2
pyrene cis-4,5-dihydrodiol + NAD+
-
-
-
-
?
pyrene + NADH + H+ + O2
pyrene cis-4,5-dihydrodiol + NAD+
-
poor substrate
-
-
?
quinazoline + NADH + H+ + O2
(5R,6S)-5,6-dihydroquinazoline-5,6-diol + quinazolin-8-ol
-
-
99% total conversion, givng 56% (5R,6S)-5,6-dihydroquinazoline-5,6-diol + 43% quinazolin-8-ol
-
?
quinazoline + NADH + H+ + O2
(5R,6S)-5,6-dihydroquinazoline-5,6-diol + quinazolin-8-ol
-
-
99% total conversion, givng 56% (5R,6S)-5,6-dihydroquinazoline-5,6-diol + 43% quinazolin-8-ol
-
?
quinoline + NADH + H+ + O2
(5R,6S)-5,6-dihydroquinoline-5,6-diol + quinolin-3-ol + NAD+
-
-
66% total conversion, giving 55% (5R,6S)-5,6-dihydroquinoline-5,6-diol and 35% quinolin-3-ol
-
?
quinoline + NADH + H+ + O2
(5R,6S)-5,6-dihydroquinoline-5,6-diol + quinolin-3-ol + NAD+
-
-
66% total conversion, giving 55% (5R,6S)-5,6-dihydroquinoline-5,6-diol and 35% quinolin-3-ol
-
?
additional information
?
-
-
the enzyme is responsible for the initial catabolic reactions onto naphthothiophenes and dibenzothiophene
-
-
?
additional information
?
-
-
biotransformation of 2-pyridone- and 2-quinolone-derived compounds by recombinant whole-cells of Escherichia coli JM109(DE3)(pDTG141) expressing the naphthalene-dioxygenase system from Pseudomonas sp. NCIB 9816-4, using a series of N- and C-substituted derivatives. Among them, only the N-methyl substituted compounds are good substrates for a regio- and stereoselective dihydroxylation reaction leading to cis-dihydroxydihydro pyridone derivatives
-
-
?
additional information
?
-
-
the enzyme is responsible for the initial catabolic reactions onto naphthothiophenes and dibenzothiophene
-
-
?
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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
Pseudomonas sp.
brenda
Haigler, B.E.; Gibson, D.T.
Purification and properties of NADH-ferredoxinNAP reductase, a component of naphthalene dioxygenase from Pseudomonas sp. strain NCIB 9816
J. Bacteriol.
172
457-464
1990
Pseudomonas sp.
brenda
Jeffrey, A.M.; Yeh, H.J.C.; Jerina, D.M.; Patel, T.R.; Davey, J.F.; Gibson, D.T.
Initial reactions in the oxidation of naphthalene by Pseudomonas putida
Biochemistry
14
575-584
1975
Pseudomonas putida, Pseudomonas putida 119
brenda
Ensley, B.D.; Gibson, D.T.
Naphthalene dioxygenase: purification and properties of a terminal oxygenase component
J. Bacteriol.
155
505-511
1983
Pseudomonas sp., Pseudomonas sp. NCIB 9816
brenda
Ensley, B.D.; Haigler, B.E.
Naphthalene dioxygenase from Pseudomonas NCIB 9816
Methods Enzymol.
188
46-52
1990
Pseudomonas sp.
brenda
Kurkela, S.; Lehvslaiho, H.; Palva, E.T.; Teeri, T.H.
Cloning, nucleotide sequence and characterization of genes encoding naphthalene dioxygenase of Pseudomonas putida strain NCIB9816
Gene
73
355-362
1988
Pseudomonas sp.
brenda
Ensley, B.D.; Gibson, D.T.; Laborde, A.L.
Oxidation of naphthalene by a multicomponent enzyme system from Pseudomonas sp. strain NCIB 9816
J. Bacteriol.
149
948-954
1982
Pseudomonas sp.
brenda
Dua, R.D.; Meera, S.
Purification and characterisation of naphthalene oxygenase from Corynebacterium renale
Eur. J. Biochem.
120
461-465
1981
Corynebacterium renale
brenda
Catterall, F.A.; Williams, P.A.
Some properties of the naphthalene oxygenase from Pseudomonas sp. NCIB 9816
J. Gen. Microbiol.
67
117-124
1971
Pseudomonas sp.
brenda
Ensley, B.D.; Ratzkin, B.J.; Osslund, T.D.; Simon, M.J.; Wackett, L.P.; Gibson, D.T.
Expression of naphthalene oxidation genes in Escherichia coli results in the biosynthesis of indigo
Science
222
167-169
1983
Pseudomonas putida, Pseudomonas putida G7
brenda
Swanson, E.P
Microbial transformation of benzocyclubutene to benzocyclobutene-1-ol and benzocyclobutene-1-one
Appl. Environ. Microbiol.
58
3404-3406
1992
Pseudomonas fluorescens
brenda
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Pseudomonas sp.
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Pseudomonas fluorescens, Pseudomonas fluorescens NCIMB 40531
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Pseudomonas sp.
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Pseudomonas sp.
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Pseudomonas sp.
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Pseudomonas sp.
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Pseudomonas sp.
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Rhodococcus sp., Rhodococcus sp. NCIMB12038
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Pseudomonas putida, Pseudomonas putida G7
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Pseudomonas sp.
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Pseudomonas sp.
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Pseudomonas sp.
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Rhodococcus sp., Rhodococcus sp. NCIMB12038
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Pseudomonas putida
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Pseudomonas sp., Pseudomonas sp. HKT554
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Pseudomonas sp.
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Pseudomonas putida, Pseudomonas putida 8859
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Sphingomonas sp.
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Pseudomonas sp., Pseudomonas sp. NCIB 9816-4
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Rhodococcus sp., Rhodococcus sp. NCIMB12038
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Pseudomonas sp., Pseudomonas sp. NCIB 9816-4
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Escherichia coli, Escherichia coli JM109(DE3)
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Escherichia coli
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Pseudomonas sp.
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Pseudomonas sp.
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Biosynthesis of indigo dye by newly isolated naphthalene-degrading strain Pseudomonas sp. HOB1 and its application in dyeing cotton fabric
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Pseudomonas sp., Pseudomonas sp. HOB1
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Pseudomonas putida (P0A110 and P0A112), Pseudomonas putida, Pseudomonas putida G7 (P0A110 and P0A112)
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Pseudomonas putida, Pseudomonas putida G7
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Pseudomonas sp., Pseudomonas sp. NCIB 9816-4
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Ralstonia sp., Ralstonia sp. U2
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Pseudomonas sp., Pseudomonas sp. NCIB 9616-4
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brenda
Yen, K.M.; Karl, M.R.
Identification of a new gene, tmoF, in the Pseudomonas mendocina KR1 gene cluster encoding toluene-4-monooxygenase
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plasmid NAH7 (Q52009), plasmid NAH7
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Dutta, K.; Shityakov, S.; Das, P.P.; Ghosh, C.
Enhanced biodegradation of mixed PAHs by mutated naphthalene 1,2-dioxygenase encoded by Pseudomonas putida strain KD6 isolated from petroleum refinery waste
3 Biotech
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Pseudomonas putida, Pseudomonas putida KD6
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Zhang, X.; Qu, Y.; Ma, Q.; Kong, C.; Zhou, H.; Cao, X.; Shen, W.; Shen, E.; Zhou, J.
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Comamonas sp. MQ (G9IE62), Comamonas sp. MQ (G9IE63)
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Dihydroxylation of four- and five-ring aromatic hydrocarbons by the naphthalene dioxygenase from Sphingomonas CHY-1
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Sphingomonas sp. CHY-1
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Jin, J.N.; Yao, J.; Zhang, Q.Y.; Yu, C.; Chen, P.; Liu, W.J.; Peng, D.N.; Choi, M.M.
An integrated approach of bioassay and molecular docking to study the dihydroxylation mechanism of pyrene by naphthalene dioxygenase in Rhodococcus sp. ustb-1
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Rhodococcus sp. ustb-1
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Ji, X.; Xu, J.; Ning, S.; Li, N.; Tan, L.; Shi, S.
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Comamonas sp. JB
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Peng, R.H.; Fu, X.Y.; Zhao, W.; Tian, Y.S.; Zhu, B.; Han, H.J.; Xu, J.; Yao, Q.H.
Phytoremediation of phenanthrene by transgenic plants transformed with a naphthalene dioxygenase system from Pseudomonas
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Pseudomonas putida
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IUCrJ
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Pseudomonas sp. (P0A111), Pseudomonas sp. C18 (P0A111)
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Escalante, D.E.; Aukema, K.G.; Wackett, L.P.; Aksan, A.
Simulation of the bottleneck controlling access into a Rieske active site Predicting substrates of naphthalene 1,2-dioxygenase
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Pseudomonas putida (P0A110), Pseudomonas putida (P0A112)
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Librando, V.; Pappalardo, M.
Theoretical approach to the innovative mutation of naphthalene 1,2-dioxygenase a molecular dynamics and docking study
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Pseudomonas putida (P0A110)
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Yang, Y.; Wang, J.; Liao, J.; Xie, S.; Huang, Y.
Distribution of naphthalene dioxygenase genes in crude oil-contaminated soils
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Pseudomonas sp.
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