1.14.12.12: naphthalene 1,2-dioxygenase
This is an abbreviated version!
For detailed information about naphthalene 1,2-dioxygenase, go to the full flat file.
Word Map on EC 1.14.12.12
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1.14.12.12
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putida
-
polycyclic
-
bioremediation
-
rieske
-
toluene
-
phenanthrene
-
dioxygenation
-
naphthalene-degrading
-
ring-hydroxylating
-
dihydroxylation
-
indigo
-
pah-degrading
-
hydrocarbon-degrading
-
dihydrodiols
-
cis-dihydrodiols
-
rieske-type
-
oil-contaminated
-
cis-dihydroxylation
-
parales
-
2-nitrotoluene
-
pah-contaminated
-
acenaphthene
-
cis-diols
-
side-on
-
alpha3beta3
-
indene
-
synthesis
- 1.14.12.12
- putida
-
polycyclic
-
bioremediation
-
rieske
- toluene
- phenanthrene
-
dioxygenation
-
naphthalene-degrading
-
ring-hydroxylating
-
dihydroxylation
- indigo
-
pah-degrading
-
hydrocarbon-degrading
- dihydrodiols
- cis-dihydrodiols
-
rieske-type
-
oil-contaminated
-
cis-dihydroxylation
-
parales
- 2-nitrotoluene
-
pah-contaminated
- acenaphthene
-
cis-diols
-
side-on
-
alpha3beta3
- indene
- synthesis
Reaction
Synonyms
NAG, NAHA, nahAc, naphthalene 1,2-dioxygenase, naphthalene dioxygenase, naphthalene oxygenase, NDO, oxygenase, naphthalene di-
ECTree
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Substrates Products
Substrates Products on EC 1.14.12.12 - naphthalene 1,2-dioxygenase
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REACTION DIAGRAM
(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
?
(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-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-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-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-methylisoquinoline + NADH + H+ + O2
cis-3-methyl-7,8-dihydroisoquinoline-7,8-diol + 3-methylisoquinolin-5-ol + 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
?
anthracene + NADH + O2
(1R,2S)-1,2-dihydroanthracene-1,2-diol + (1S,2R)-1,2-dihydroanthracene-1,2-diol + NAD+
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]pyrene + NADH + H+ + O2
cis-9,10-dihydroxy-9,10-dihydrobenzo[a]pyrene + NAD+
-
-
-
-
?
benzo[rst]dinaphtho[defg,ijkl]pentaphene + NADH + H+ + O2
?
-
-
-
?
benzo[rst]phenanthro[1,10,9-cde]pentaphene + 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+
-
-
-
-
?
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+
-
-
-
-
?
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
?
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
-
-
?
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
?
indene + NADH + O2
(1S)-indenol + (1R,2S)-indandiol + NAD+
-
recombinant enzyme
57.9% indenol, 29.6% indandiol
?
indole + NADH + H+ + O2
cis-indole-2,3-dihydrodiol + 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+
phenetole + NADH + H+ + O2
phenol + vinyloxybenzene + (S)-ethylphenyl sulfoxide + 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
?
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
-
?
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
-
?
? + NAD+
-
-
generation of mono- and dioxygenated products
-
?
1,2,4-trimethylnaphthalene + NADH + H+ + O2
? + NAD+
-
-
generation of mono- and dioxygenated products
-
?
? + 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
-
?
(R)-1,3-benzodithiole-1-oxide + NAD+
-
-
-
-
?
1,3-benzodithiole + NADH + O2
(R)-1,3-benzodithiole-1-oxide + NAD+
-
-
-
-
?
(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+
-
-
-
-
?
? + NAD+
-
-
generation of monooxygenated products
-
?
1,4-dimethylnaphthalene + NADH + H+ + O2
? + NAD+
-
-
generation of monooxygenated products
-
?
? + NAD+
-
-
generation of monooxygenated products
-
?
1,5-dimethylnaphthalene + NADH + H+ + O2
? + NAD+
-
-
generation of monooxygenated products
-
?
(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+
-
-
-
?
(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-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
-
?
(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
-
?
(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
-
?
(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-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
-
?
chlorohydroquinone + 4-chlorocatechol + NAD+
-
-
-
-
?
3-chlorophenol + NADH + O2
chlorohydroquinone + 4-chlorocatechol + NAD+
-
-
-
-
?
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+
-
-
-
-
?
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
-
?
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
-
?
(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+
-
-
-
-
?
(S)-1-phenylethanol + (R)-1-phenylethanol + NAD+
-
-
-
?
ethylbenzene + NADH + H+ + O2
(S)-1-phenylethanol + (R)-1-phenylethanol + NAD+
-
-
-
?
(R)-ethylphenyl sulfoxide + NAD+
-
-
-
?
ethylphenyl sulfide + NADH + H+ + O2
(R)-ethylphenyl sulfoxide + NAD+
-
-
-
?
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 + 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+
-
-
-
-
?
methylhydroquinone + 3-methylcatechol + 4-methylcatechol + NAD+
-
-
-
-
?
m-cresol + NADH + O2
methylhydroquinone + 3-methylcatechol + 4-methylcatechol + NAD+
-
-
-
-
?
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)+
-
-
-
?
(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+
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-
-
?
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
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-
?
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+
-
-
-
-
?
1,2-dihydronaphthalene-1,2-diol + NAD+
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-
-
-
?
naphthalene + NADH + H+ + O2
1,2-dihydronaphthalene-1,2-diol + NAD+
-
-
-
-
?
(1R,2S)-1,2-dihydronaphthalene-1,2-diol + NAD+
-
initial oxidative reaction in bacterial naphthalene catabolism
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?
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+
-
-
-
-
?
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+
-
-
-
?
(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+
-
poor substrate
-
-
?
(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
-
?
(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
-
?
?
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-
the enzyme is responsible for the initial catabolic reactions onto naphthothiophenes and dibenzothiophene
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-
?
additional information
?
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-
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
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-
?
additional information
?
-
-
the enzyme is responsible for the initial catabolic reactions onto naphthothiophenes and dibenzothiophene
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-
?