1.14.13.236: toluene 4-monooxygenase
This is an abbreviated version!
For detailed information about toluene 4-monooxygenase, go to the full flat file.
Word Map on EC 1.14.13.236
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1.14.13.236
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hydroxylase
-
diiron
-
mendocina
-
p-cresol
-
regiospecificity
-
ferredoxins
-
cepacia
-
rieske
-
synthesis
-
pickettii
-
ortho-monooxygenase
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m-nitrophenol
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nitrobenzene
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2-naphthol
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3-monooxygenase
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rieske-type
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four-protein
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diferric
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o-xylene
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norcarane
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xanthobacter
-
analysis
- 1.14.13.236
- hydroxylase
-
diiron
- mendocina
- p-cresol
-
regiospecificity
- ferredoxins
- cepacia
-
rieske
- synthesis
- pickettii
-
ortho-monooxygenase
- m-nitrophenol
- nitrobenzene
- 2-naphthol
-
3-monooxygenase
-
rieske-type
-
four-protein
-
diferric
- o-xylene
- norcarane
- xanthobacter
- analysis
Reaction
Synonyms
T4moD, T4moF, T4MOH, TMO, TmoA, TmoC, TmoF, toluene-4-monooxygenase system protein A, TOM, TomA3
ECTree
1.14.13.236 toluene 4-monooxygenaseAdvanced search results
results (
results (Substrates Products
Substrates Products on EC 1.14.13.236 - toluene 4-monooxygenase
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SUBSTRATE 
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
2 indole + 3 NADH + 3 H+ + 3 O2
indirubin + 3 NAD+ + 3 H2O
A0A0D3QM77; A0A0D3QME2; A0A0D3QLU4; A0A0D3QM47; A0A0D3QMJ7; A0A0D3QM80
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reaction via C-3 oxidation to indoxyl, oxidation to isatin, and recombinantion of isatin and indoxyl to indirubin
-
?
methoxybenzene + NADH + H+ + O2
4-methoxyphenol + NAD+ + H2O
-
more than 99% 4-methoxyphenol
-
?
norcarane + NADH + H+ + O2
endo-2-norcaranol + exo-2-norcaranol + endo-3-norcaranol + NAD+ + H2O
1,1-diethylcyclopropane + NADH + H+ + O2
? + NAD+ + H2O
-
-
-
?
1,1-diethylcyclopropane + NADH + H+ + O2
? + NAD+ + H2O
-
-
-
?
1,1-dimethylcyclopropane + NADH + H+ + O2
? + NAD+ + H2O
-
-
-
?
1,1-dimethylcyclopropane + NADH + H+ + O2
? + NAD+ + H2O
-
-
-
?
2 fluorobenzene + NADH + H+ + O2
4-fluorophenol + 4-fluorocatechol + NAD+ + H2O
-
whole-cell reaction, the predominant product is either 4-fluorophenol or 4-fluorocatechol depending on the ratio of biocatalyst to substrate concentration
-
?
2 fluorobenzene + NADH + H+ + O2
4-fluorophenol + 4-fluorocatechol + NAD+ + H2O
-
whole-cell reaction, the predominant product is either 4-fluorophenol or 4-fluorocatechol depending on the ratio of biocatalyst to substrate concentration
-
?
2-phenylethanol + 2 NADH + 2 H+ + O2
3,4-dihydroxyphenylethanol + 2 NAD+ + 2 H2O
-
reaction of mutants I100A, I100S, I100G
-
?
2-phenylethanol + 2 NADH + 2 H+ + O2
3,4-dihydroxyphenylethanol + 2 NAD+ + 2 H2O
-
reaction of mutants I100A, I100S, I100G
-
?
2-phenylethanol + NADH + H+ + O2
m-tyrosol + p-tyrosol + NAD+ + H2O
-
63% m-tyosol + 37% p-tyrosol
-
?
2-phenylethanol + NADH + H+ + O2
m-tyrosol + p-tyrosol + NAD+ + H2O
-
63% m-tyosol + 37% p-tyrosol
-
?
2-phenylethanol + NADH + H+ + O2
o-tyrosol + m-tyrosol + NAD+ + H2O
-
64% o-tyrosol + 36% m-tyrosol
-
?
2-phenylethanol + NADH + H+ + O2
o-tyrosol + m-tyrosol + NAD+ + H2O
-
64% o-tyrosol + 36% m-tyrosol
-
?
2-xylene + NADH + H+ + O2
3,4-dimethylphenol + NAD+ + H2O
-
95% 3,4-dimethylphenol plus 5% 2-methyl benzyl alcohol
-
?
2-xylene + NADH + H+ + O2
3,4-dimethylphenol + NAD+ + H2O
-
95% 3,4-dimethylphenol plus 5% 2-methyl benzyl alcohol
-
?
3-xylene + NADH + H+ + O2
2,4-dimethylphenol + NAD+ + H2O
-
97% 2,4-dimethylphenol plus 2.5% 3-methyl benzyl alcohol plus 0.5% 3,5-dimethylphenol
-
?
3-xylene + NADH + H+ + O2
2,4-dimethylphenol + NAD+ + H2O
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97% 2,4-dimethylphenol plus 2.5% 3-methyl benzyl alcohol plus 0.5% 3,5-dimethylphenol
-
?
4-xylene + NADH + H+ + O2
2,5-dimethylphenol + 4-methyl benzyl alcohol + NAD+ + H2O
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82% 2,5-dimethylphenol plus 18% 4-methyl benzyl alcohol
-
?
4-xylene + NADH + H+ + O2
2,5-dimethylphenol + 4-methyl benzyl alcohol + NAD+ + H2O
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82% 2,5-dimethylphenol plus 18% 4-methyl benzyl alcohol
-
?
anisole + NADH + H+ + O2
4-methoxyphenol + NAD+ + H2O
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87% efficiency
-
?
anisole + NADH + H+ + O2
4-methoxyphenol + NAD+ + H2O
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87% efficiency
-
?
benzene + NADH + H+ + O2
phenol + NAD+ + H2O
-
98% efficiency
-
?
benzene + NADH + H+ + O2
phenol + NAD+ + H2O
-
98% efficiency
-
?
benzene + NADH + H+ + O2
phenol + NAD+ + H2O
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sole product
-
?
chlorobenzene + NADH + H+ + O2
4-chlorophenol + NAD+ + H2O
-
39% efficiency
-
?
chlorobenzene + NADH + H+ + O2
4-chlorophenol + NAD+ + H2O
-
more than 95% 4-chlorophenol
-
?
chlorobenzene + NADH + H+ + O2
4-chlorophenol + NAD+ + H2O
-
39% efficiency
-
?
m-cresol + NADH + H+ + O2
4-methylcatechol + NAD+ + H2O
Q6Q8Q7; Q6Q8Q6; Q6Q8Q5; Q6Q8Q4; Q6Q8Q3; Q6Q8Q2
-
100% 4-methylcatechol
-
?
m-cresol + NADH + H+ + O2
4-methylcatechol + NAD+ + H2O
Q6Q8Q7; Q6Q8Q6; Q6Q8Q5; Q6Q8Q4; Q6Q8Q3; Q6Q8Q2
-
100% 4-methylcatechol
-
?
m-tyrosol + 2 NADH + 2 H+ + O2
2,3-dihydroxyphenylethanol + 2 NAD+ + 2 H2O
-
9% 2,3-dihydroxyphenylethanol
-
?
m-tyrosol + 2 NADH + 2 H+ + O2
2,3-dihydroxyphenylethanol + 2 NAD+ + 2 H2O
-
9% 2,3-dihydroxyphenylethanol
-
?
m-tyrosol + 2 NADH + 2 H+ + O2
3,4-dihydroxyphenylethanol + 2 NAD+ + 2 H2O
-
mutants I100A, I100S, I100D, I100V and I100G hydroxylate m-tyrosol to form 3,4-dihydroxyphenylethanol with conversion of 55%, 50%, 2%, 3% and 18%, respectively
-
?
m-tyrosol + 2 NADH + 2 H+ + O2
3,4-dihydroxyphenylethanol + 2 NAD+ + 2 H2O
-
mutants I100A, I100S, I100D, I100V and I100G hydroxylate m-tyrosol to form 3,4-dihydroxyphenylethanol with conversion of 55%, 50%, 2%, 3% and 18%, respectively
-
?
methyl 4-tolyl sulfide + NADH + H+ + O2
methyl 4-tolyl sulfoxide + NAD+ + H2O
-
(pro-S)-sulfoxide, 11% enantiomeric excess
-
?
methyl 4-tolyl sulfide + NADH + H+ + O2
methyl 4-tolyl sulfoxide + NAD+ + H2O
-
(pro-S)-sulfoxide, 11% enantiomeric excess
-
?
methyl 4-tolyl sulfide + NADH + H+ + O2
methyl 4-tolyl sulfoxide + NAD+ + H2O
-
(pro-R)-sulfoxide, 41% enantiomeric excess
-
?
methyl 4-tolyl sulfide + NADH + H+ + O2
methyl 4-tolyl sulfoxide + NAD+ + H2O
-
(pro-R)-sulfoxide, 41% enantiomeric excess
-
?
methyl p-tolyl sulfide + NADH + H+ + O2
methyl p-tolyl sulfoxide + NAD+ + H2O
Q6Q8Q7; Q6Q8Q6; Q6Q8Q5; Q6Q8Q4; Q6Q8Q3; Q6Q8Q2
-
-
-
?
methyl p-tolyl sulfide + NADH + H+ + O2
methyl p-tolyl sulfoxide + NAD+ + H2O
Q6Q8Q7; Q6Q8Q6; Q6Q8Q5; Q6Q8Q4; Q6Q8Q3; Q6Q8Q2
-
-
-
?
methyl phenyl sulfide + NADH + H+ + O2
methyl phenyl sulfoxide + NAD+ + H2O
-
(pro-S)-sulfoxide, 51% enantiomeric excess
-
?
methyl phenyl sulfide + NADH + H+ + O2
methyl phenyl sulfoxide + NAD+ + H2O
-
(pro-S)-sulfoxide, 51% enantiomeric excess
-
?
methyl phenyl sulfide + NADH + H+ + O2
methyl phenyl sulfoxide + NAD+ + H2O
-
(pro-S)-sulfoxide, 86% enantiomeric excess
-
?
methyl phenyl sulfide + NADH + H+ + O2
methyl phenyl sulfoxide + NAD+ + H2O
-
(pro-S)-sulfoxide, 86% enantiomeric excess
-
?
naphthalene + NADH + H+ + O2
2-naphthol + NAD+ + H2O
-
-
-
?
nitrobenzene + NADH + H+ + O2
4-nitrophenol + NAD+ + H2O
-
12% efficiency
-
?
nitrobenzene + NADH + H+ + O2
4-nitrophenol + NAD+ + H2O
-
88% 4-nitrophenol plus 9% 3-nitrophenol plus 3% 2-nitrophenol
-
?
nitrobenzene + NADH + H+ + O2
4-nitrophenol + NAD+ + H2O
-
12% efficiency
-
?
norcarane + NADH + H+ + O2
endo-2-norcaranol + exo-2-norcaranol + endo-3-norcaranol + NAD+ + H2O
-
72% coupling, 47.5% endo-2-norcaranol, 39.2% exo-2- and endo-3-norcaranol, 8.8% exo-3-norcaranol
-
?
norcarane + NADH + H+ + O2
endo-2-norcaranol + exo-2-norcaranol + endo-3-norcaranol + NAD+ + H2O
-
72% coupling, 47.5% endo-2-norcaranol, 39.2% exo-2- and endo-3-norcaranol, 8.8% exo-3-norcaranol
-
?
o-cresol + NADH + H+ + O2
3-methylcatechol + NAD+ + H2O
Q6Q8Q7; Q6Q8Q6; Q6Q8Q5; Q6Q8Q4; Q6Q8Q3; Q6Q8Q2
-
91% 3-methylcatechol + 9% methylhydroquinone
-
?
o-cresol + NADH + H+ + O2
3-methylcatechol + NAD+ + H2O
Q6Q8Q7; Q6Q8Q6; Q6Q8Q5; Q6Q8Q4; Q6Q8Q3; Q6Q8Q2
-
91% 3-methylcatechol + 9% methylhydroquinone
-
?
o-methoxyphenol + NADH + H+ + O2
4-methoxyresorcinol + 3-methoxycatechol + NAD+ + H2O
Q6Q8Q7; Q6Q8Q6; Q6Q8Q5; Q6Q8Q4; Q6Q8Q3; Q6Q8Q2
-
87% 4-methoxyresorcinol, 11% 3-methoxycatechol, and 2% methoxyhydroquinone
-
?
o-methoxyphenol + NADH + H+ + O2
4-methoxyresorcinol + 3-methoxycatechol + NAD+ + H2O
Q6Q8Q7; Q6Q8Q6; Q6Q8Q5; Q6Q8Q4; Q6Q8Q3; Q6Q8Q2
-
87% 4-methoxyresorcinol, 11% 3-methoxycatechol, and 2% methoxyhydroquinone
-
?
o-tyrosol + 2 NADH + 2 H+ + O2
2,3-dihydroxyphenylethanol + 2 NAD+ + 2 H2O
-
mutants I100A, I100S and I100G hydroxylate p-tyrosol to form 3,4-dihydroxyphenylethanol with 24%, 11% and 13% conversion, respectively, respectively
-
?
o-tyrosol + 2 NADH + 2 H+ + O2
2,3-dihydroxyphenylethanol + 2 NAD+ + 2 H2O
-
mutants I100A, I100S and I100G hydroxylate p-tyrosol to form 3,4-dihydroxyphenylethanol with 24%, 11% and 13% conversion, respectively, respectively
-
?
o-tyrosol + NADH + H+ + O2
2,3-dihydroxyphenylethanol + NAD+ + H2O
-
83% 2,3-dihydroxyphenylethanol
-
?
o-tyrosol + NADH + H+ + O2
2,3-dihydroxyphenylethanol + NAD+ + H2O
-
83% 2,3-dihydroxyphenylethanol
-
?
o-tyrosol + NADH + H+ + O2
2,3-dihydroxyphenylethanol + NAD+ + H2O
reaction of mutant S395C, 18% conversion in 44 h
-
-
?
p-cresol + NADH + H+ + O2
4-methylcatechol + NAD+ + H2O
Q6Q8Q7; Q6Q8Q6; Q6Q8Q5; Q6Q8Q4; Q6Q8Q3; Q6Q8Q2
-
100% 4-methylcatechol
-
?
p-cresol + NADH + H+ + O2
4-methylcatechol + NAD+ + H2O
Q6Q8Q7; Q6Q8Q6; Q6Q8Q5; Q6Q8Q4; Q6Q8Q3; Q6Q8Q2
-
100% 4-methylcatechol
-
?
p-tyrosol + 2 NADH + 2 H+ + O2
3,4-dihydroxyphenylethanol + 2 NAD+ + 2 H2O
-
10% 3,4-dihydroxyphenylethanol
-
?
p-tyrosol + 2 NADH + 2 H+ + O2
3,4-dihydroxyphenylethanol + 2 NAD+ + 2 H2O
-
10% 3,4-dihydroxyphenylethanol
-
?
p-tyrosol + 2 NADH + 2 H+ + O2
3,4-dihydroxyphenylethanol + 2 NAD+ + 2 H2O
-
mutants I100A, I100S and I100G hydroxylate p-tyrosol to form 3,4-dihydroxyphenylethanol with 65%, 48% and 98% conversion, respectively, respectively
-
?
phenylethanol + NADH + H+ + O2
m-tyrosol + p-tyrosol + NAD+ + H2O
Q6Q8Q7; Q6Q8Q6; Q6Q8Q5; Q6Q8Q4; Q6Q8Q3; Q6Q8Q2
-
63% m-tyrosol + 37% p-tyrosol
-
?
phenylethanol + NADH + H+ + O2
m-tyrosol + p-tyrosol + NAD+ + H2O
Q6Q8Q7; Q6Q8Q6; Q6Q8Q5; Q6Q8Q4; Q6Q8Q3; Q6Q8Q2
-
63% m-tyrosol + 37% p-tyrosol
-
?
styrene + NADH + H+ + O2
styrene epoxide + NAD+ + H2O
Q6Q8Q7; Q6Q8Q6; Q6Q8Q5; Q6Q8Q4; Q6Q8Q3; Q6Q8Q2
-
-
-
?
styrene + NADH + H+ + O2
styrene epoxide + NAD+ + H2O
Q6Q8Q7; Q6Q8Q6; Q6Q8Q5; Q6Q8Q4; Q6Q8Q3; Q6Q8Q2
-
-
-
?
toluene + NADH + H+ + O2
4-methylphenol + NAD+ + H2O
-
-
-
?
toluene + NADH + H+ + O2
4-methylphenol + NAD+ + H2O
-
-
-
?
toluene + NADH + H+ + O2
4-methylphenol + NAD+ + H2O
-
194% efficiency
-
?
toluene + NADH + H+ + O2
4-methylphenol + NAD+ + H2O
-
94% coupling
-
?
toluene + NADH + H+ + O2
4-methylphenol + NAD+ + H2O
Q6Q8Q7; Q6Q8Q6; Q6Q8Q5; Q6Q8Q4; Q6Q8Q3; Q6Q8Q2
-
96% 4-methylphenol + 3% 3-methylphenol
-
?
toluene + NADH + H+ + O2
4-methylphenol + NAD+ + H2O
-
96% 4-methylphenol plus 2.8% 3-methylphenol plus 0.4% 2-methylphenol
-
?
toluene + NADH + H+ + O2
4-methylphenol + NAD+ + H2O
-
96% 4-methylphenol plus 2.8% 3-methylphenol plus 0.4% 2-methylphenol plus 0.8% benzyl alcohol
-
?
toluene + NADH + H+ + O2
4-methylphenol + NAD+ + H2O
-
96.2% 4-methylphenol, 1.5% 3-methylphenol, 0.9% 2-methylphenol, 1.4% benzyl alcohol
-
?
toluene + NADH + H+ + O2
4-methylphenol + NAD+ + H2O
-
-
-
?
toluene + NADH + H+ + O2
4-methylphenol + NAD+ + H2O
-
96% 4-methylphenol plus 2.8% 3-methylphenol plus 0.4% 2-methylphenol plus 0.8% benzyl alcohol
-
?
toluene + NADH + H+ + O2
4-methylphenol + NAD+ + H2O
-
194% efficiency
-
?
toluene + NADH + H+ + O2
4-methylphenol + NAD+ + H2O
-
-
-
?
toluene + NADH + H+ + O2
4-methylphenol + NAD+ + H2O
-
94% coupling
-
?
toluene + NADH + H+ + O2
4-methylphenol + NAD+ + H2O
-
-
-
?
toluene + NADH + H+ + O2
4-methylphenol + NAD+ + H2O
Q6Q8Q7; Q6Q8Q6; Q6Q8Q5; Q6Q8Q4; Q6Q8Q3; Q6Q8Q2
-
96% 4-methylphenol + 3% 3-methylphenol
-
?
toluene + NADH + H+ + O2
p-cresol + NAD+ + H2O
-
-
-
?
toluene + NADH + H+ + O2
p-cresol + NAD+ + H2O
-
-
-
?
additional information
?
-
no substrates for wild-type: o-tyrosol, m-tyrosol, p-tyrosol
-
-
?
additional information
?
-
no substrates for wild-type: o-tyrosol, m-tyrosol, p-tyrosol
-
-
?
additional information
?
-
experiments with p-deuterotoluene lead to the isolation of p-cresol which retains 68% of the deuterium initially present in the parent molecule. When incubated with toluene in the presence of 1802, the oxygen in p-cresol is derived from molecular oxygen
-
-
?
additional information
?
-
highly specific for para hydroxylation of toluene, o-xylene, m-xylene
-
-
?
additional information
?
-
no substrates for wild-type: o-tyrosol, m-tyrosol, p-tyrosol
-
-
?
additional information
?
-
products are consistent with both radical rearrangement and cation ring expansion. Products show high-fidelity incorporation of an O-atom from O2 in the un-rearranged and radical-rearranged products, while the O-atom found in the cation ring-expansion products is predominantly obtained by reaction with H2O
-
-
?
additional information
?
-
highly specific for para hydroxylation of toluene, o-xylene, m-xylene
-
-
?
additional information
?
-
-
highly specific for para hydroxylation of toluene, o-xylene, m-xylene
-
-
?
additional information
?
-
no substrates for wild-type: o-tyrosol, m-tyrosol, p-tyrosol
-
-
?
additional information
?
-
products are consistent with both radical rearrangement and cation ring expansion. Products show high-fidelity incorporation of an O-atom from O2 in the un-rearranged and radical-rearranged products, while the O-atom found in the cation ring-expansion products is predominantly obtained by reaction with H2O
-
-
?
additional information
?
-
experiments with p-deuterotoluene lead to the isolation of p-cresol which retains 68% of the deuterium initially present in the parent molecule. When incubated with toluene in the presence of 1802, the oxygen in p-cresol is derived from molecular oxygen
-
-
?
