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Information on EC 1.14.13.236 - toluene 4-monooxygenase
for references in articles please use BRENDA:EC1.14.13.236
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EC Tree 1 Oxidoreductases
1.14 Acting on paired donors, with incorporation or reduction of molecular oxygen
1.14.13 With NADH or NADPH as one donor, and incorporation of one atom of oxygen into the other donor
1.14.13.236 toluene 4-monooxygenase
IUBMB Comments
This bacterial enzyme belongs to a family of soluble diiron hydroxylases that includes toluene-, benzene-, xylene- and methane monooxygenases, phenol hydroxylases, and alkene epoxidases. The enzyme comprises a four-component complex that includes a hydroxylase, NADH-ferredoxin oxidoreductase, a Rieske-type [2Fe-2S] ferredoxin, and an effector protein.
The enzyme appears in viruses and cellular organisms
- 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
showSynonyms
toluene 4-monooxygenase, t4mod, t4moh, t4mof, toma3, more
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
T4moF
T4MOH
TMO
-
-
-
-
TmoA
TmoC
TmoF
toluene-4-monooxygenase system protein A
TOM
TomA3
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
toluene + NADH + H+ + O2 = 4-methylphenol + NAD+ + H2O
-
-
-
-
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PATHWAY SOURCE
PATHWAYS
BRENDA
MetaCyc
benzene degradation II (aerobic), toluene degradation II (aerobic) (via 4-methylcatechol), toluene degradation to 4-methylphenol
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SYSTEMATIC NAME
IUBMB Comments
toluene,NADH:oxygen oxidoreductase (4-hydroxylating)
This bacterial enzyme belongs to a family of soluble diiron hydroxylases that includes toluene-, benzene-, xylene- and methane monooxygenases, phenol hydroxylases, and alkene epoxidases. The enzyme comprises a four-component complex that includes a hydroxylase, NADH-ferredoxin oxidoreductase, a Rieske-type [2Fe-2S] ferredoxin, and an effector protein.
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
LITERATURE
COMMENTARY
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
Substrates: -
Products: reaction via C-3 oxidation to indoxyl, oxidation to isatin, and recombinantion of isatin and indoxyl to indirubin
Products: 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
Substrates: -
Products: more than 99% 4-methoxyphenol
Products: 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
Substrates: -
Products: -
Products: -
?
1,1-diethylcyclopropane + NADH + H+ + O2
? + NAD+ + H2O
Substrates: -
Products: -
Products: -
?
1,1-dimethylcyclopropane + NADH + H+ + O2
? + NAD+ + H2O
Substrates: -
Products: -
Products: -
?
1,1-dimethylcyclopropane + NADH + H+ + O2
? + NAD+ + H2O
Substrates: -
Products: -
Products: -
?
2 fluorobenzene + NADH + H+ + O2
4-fluorophenol + 4-fluorocatechol + NAD+ + H2O
Substrates: -
Products: whole-cell reaction, the predominant product is either 4-fluorophenol or 4-fluorocatechol depending on the ratio of biocatalyst to substrate concentration
Products: 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
Substrates: -
Products: whole-cell reaction, the predominant product is either 4-fluorophenol or 4-fluorocatechol depending on the ratio of biocatalyst to substrate concentration
Products: 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
Substrates: -
Products: reaction of mutants I100A, I100S, I100G
Products: reaction of mutants I100A, I100S, I100G
?
2-phenylethanol + 2 NADH + 2 H+ + O2
3,4-dihydroxyphenylethanol + 2 NAD+ + 2 H2O
Substrates: -
Products: reaction of mutants I100A, I100S, I100G
Products: reaction of mutants I100A, I100S, I100G
?
2-phenylethanol + NADH + H+ + O2
m-tyrosol + p-tyrosol + NAD+ + H2O
Substrates: -
Products: 63% m-tyosol + 37% p-tyrosol
Products: 63% m-tyosol + 37% p-tyrosol
?
2-phenylethanol + NADH + H+ + O2
m-tyrosol + p-tyrosol + NAD+ + H2O
Substrates: -
Products: 63% m-tyosol + 37% p-tyrosol
Products: 63% m-tyosol + 37% p-tyrosol
?
2-phenylethanol + NADH + H+ + O2
o-tyrosol + m-tyrosol + NAD+ + H2O
Substrates: -
Products: 64% o-tyrosol + 36% m-tyrosol
Products: 64% o-tyrosol + 36% m-tyrosol
?
2-phenylethanol + NADH + H+ + O2
o-tyrosol + m-tyrosol + NAD+ + H2O
Substrates: -
Products: 64% o-tyrosol + 36% m-tyrosol
Products: 64% o-tyrosol + 36% m-tyrosol
?
2-xylene + NADH + H+ + O2
3,4-dimethylphenol + NAD+ + H2O
Substrates: -
Products: 95% 3,4-dimethylphenol plus 5% 2-methyl benzyl alcohol
Products: 95% 3,4-dimethylphenol plus 5% 2-methyl benzyl alcohol
?
2-xylene + NADH + H+ + O2
3,4-dimethylphenol + NAD+ + H2O
Substrates: -
Products: 95% 3,4-dimethylphenol plus 5% 2-methyl benzyl alcohol
Products: 95% 3,4-dimethylphenol plus 5% 2-methyl benzyl alcohol
?
3-xylene + NADH + H+ + O2
2,4-dimethylphenol + NAD+ + H2O
Substrates: -
Products: 97% 2,4-dimethylphenol plus 2.5% 3-methyl benzyl alcohol plus 0.5% 3,5-dimethylphenol
Products: 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
Substrates: -
Products: 97% 2,4-dimethylphenol plus 2.5% 3-methyl benzyl alcohol plus 0.5% 3,5-dimethylphenol
Products: 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
Substrates: -
Products: 82% 2,5-dimethylphenol plus 18% 4-methyl benzyl alcohol
Products: 82% 2,5-dimethylphenol plus 18% 4-methyl benzyl alcohol
?
4-xylene + NADH + H+ + O2
2,5-dimethylphenol + 4-methyl benzyl alcohol + NAD+ + H2O
Substrates: -
Products: 82% 2,5-dimethylphenol plus 18% 4-methyl benzyl alcohol
Products: 82% 2,5-dimethylphenol plus 18% 4-methyl benzyl alcohol
?
anisole + NADH + H+ + O2
4-methoxyphenol + NAD+ + H2O
Substrates: -
Products: 87% efficiency
Products: 87% efficiency
?
anisole + NADH + H+ + O2
4-methoxyphenol + NAD+ + H2O
Substrates: -
Products: 87% efficiency
Products: 87% efficiency
?
benzene + NADH + H+ + O2
phenol + NAD+ + H2O
Substrates: -
Products: -
Products: -
?
benzene + NADH + H+ + O2
phenol + NAD+ + H2O
Substrates: -
Products: sole product
Products: sole product
?
benzene + NADH + H+ + O2
phenol + NAD+ + H2O
Substrates: -
Products: 98% efficiency
Products: 98% efficiency
?
benzene + NADH + H+ + O2
phenol + NAD+ + H2O
Substrates: -
Products: -
Products: -
?
benzene + NADH + H+ + O2
phenol + NAD+ + H2O
Substrates: -
Products: 98% efficiency
Products: 98% efficiency
?
benzene + NADH + H+ + O2
phenol + NAD+ + H2O
Substrates: -
Products: sole product
Products: sole product
?
chlorobenzene + NADH + H+ + O2
4-chlorophenol + NAD+ + H2O
Substrates: -
Products: 39% efficiency
Products: 39% efficiency
?
chlorobenzene + NADH + H+ + O2
4-chlorophenol + NAD+ + H2O
Substrates: -
Products: more than 95% 4-chlorophenol
Products: more than 95% 4-chlorophenol
?
chlorobenzene + NADH + H+ + O2
4-chlorophenol + NAD+ + H2O
Substrates: -
Products: 39% efficiency
Products: 39% efficiency
?
m-cresol + NADH + H+ + O2
4-methylcatechol + NAD+ + H2O
Q6Q8Q7; Q6Q8Q6; Q6Q8Q5; Q6Q8Q4; Q6Q8Q3; Q6Q8Q2
Substrates: -
Products: 100% 4-methylcatechol
Products: 100% 4-methylcatechol
?
m-cresol + NADH + H+ + O2
4-methylcatechol + NAD+ + H2O
Q6Q8Q7; Q6Q8Q6; Q6Q8Q5; Q6Q8Q4; Q6Q8Q3; Q6Q8Q2
Substrates: -
Products: 100% 4-methylcatechol
Products: 100% 4-methylcatechol
?
m-tyrosol + 2 NADH + 2 H+ + O2
2,3-dihydroxyphenylethanol + 2 NAD+ + 2 H2O
Substrates: -
Products: 9% 2,3-dihydroxyphenylethanol
Products: 9% 2,3-dihydroxyphenylethanol
?
m-tyrosol + 2 NADH + 2 H+ + O2
2,3-dihydroxyphenylethanol + 2 NAD+ + 2 H2O
Substrates: -
Products: 9% 2,3-dihydroxyphenylethanol
Products: 9% 2,3-dihydroxyphenylethanol
?
m-tyrosol + 2 NADH + 2 H+ + O2
3,4-dihydroxyphenylethanol + 2 NAD+ + 2 H2O
Substrates: -
Products: 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
Products: 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
Substrates: -
Products: 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
Products: 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
Substrates: -
Products: (pro-S)-sulfoxide, 11% enantiomeric excess
Products: (pro-S)-sulfoxide, 11% enantiomeric excess
?
methyl 4-tolyl sulfide + NADH + H+ + O2
methyl 4-tolyl sulfoxide + NAD+ + H2O
Substrates: -
Products: (pro-S)-sulfoxide, 11% enantiomeric excess
Products: (pro-S)-sulfoxide, 11% enantiomeric excess
?
methyl 4-tolyl sulfide + NADH + H+ + O2
methyl 4-tolyl sulfoxide + NAD+ + H2O
Substrates: -
Products: (pro-R)-sulfoxide, 41% enantiomeric excess
Products: (pro-R)-sulfoxide, 41% enantiomeric excess
?
methyl 4-tolyl sulfide + NADH + H+ + O2
methyl 4-tolyl sulfoxide + NAD+ + H2O
Substrates: -
Products: (pro-R)-sulfoxide, 41% enantiomeric excess
Products: (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
Substrates: -
Products: -
Products: -
?
methyl p-tolyl sulfide + NADH + H+ + O2
methyl p-tolyl sulfoxide + NAD+ + H2O
Q6Q8Q7; Q6Q8Q6; Q6Q8Q5; Q6Q8Q4; Q6Q8Q3; Q6Q8Q2
Substrates: -
Products: -
Products: -
?
methyl phenyl sulfide + NADH + H+ + O2
methyl phenyl sulfoxide + NAD+ + H2O
Substrates: -
Products: (pro-S)-sulfoxide, 51% enantiomeric excess
Products: (pro-S)-sulfoxide, 51% enantiomeric excess
?
methyl phenyl sulfide + NADH + H+ + O2
methyl phenyl sulfoxide + NAD+ + H2O
Substrates: -
Products: (pro-S)-sulfoxide, 51% enantiomeric excess
Products: (pro-S)-sulfoxide, 51% enantiomeric excess
?
methyl phenyl sulfide + NADH + H+ + O2
methyl phenyl sulfoxide + NAD+ + H2O
Substrates: -
Products: (pro-S)-sulfoxide, 86% enantiomeric excess
Products: (pro-S)-sulfoxide, 86% enantiomeric excess
?
methyl phenyl sulfide + NADH + H+ + O2
methyl phenyl sulfoxide + NAD+ + H2O
Substrates: -
Products: (pro-S)-sulfoxide, 86% enantiomeric excess
Products: (pro-S)-sulfoxide, 86% enantiomeric excess
?
naphthalene + NADH + H+ + O2
2-naphthol + NAD+ + H2O
Substrates: -
Products: -
Products: -
?
naphthalene + NADH + H+ + O2
2-naphthol + NAD+ + H2O
Substrates: -
Products: -
Products: -
?
nitrobenzene + NADH + H+ + O2
4-nitrophenol + NAD+ + H2O
Substrates: -
Products: 12% efficiency
Products: 12% efficiency
?
nitrobenzene + NADH + H+ + O2
4-nitrophenol + NAD+ + H2O
Substrates: -
Products: 88% 4-nitrophenol plus 9% 3-nitrophenol plus 3% 2-nitrophenol
Products: 88% 4-nitrophenol plus 9% 3-nitrophenol plus 3% 2-nitrophenol
?
nitrobenzene + NADH + H+ + O2
4-nitrophenol + NAD+ + H2O
Substrates: -
Products: 12% efficiency
Products: 12% efficiency
?
norcarane + NADH + H+ + O2
endo-2-norcaranol + exo-2-norcaranol + endo-3-norcaranol + NAD+ + H2O
Substrates: -
Products: 72% coupling, 47.5% endo-2-norcaranol, 39.2% exo-2- and endo-3-norcaranol, 8.8% exo-3-norcaranol
Products: 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
Substrates: -
Products: 72% coupling, 47.5% endo-2-norcaranol, 39.2% exo-2- and endo-3-norcaranol, 8.8% exo-3-norcaranol
Products: 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
Substrates: -
Products: 91% 3-methylcatechol + 9% methylhydroquinone
Products: 91% 3-methylcatechol + 9% methylhydroquinone
?
o-cresol + NADH + H+ + O2
3-methylcatechol + NAD+ + H2O
Q6Q8Q7; Q6Q8Q6; Q6Q8Q5; Q6Q8Q4; Q6Q8Q3; Q6Q8Q2
Substrates: -
Products: 91% 3-methylcatechol + 9% methylhydroquinone
Products: 91% 3-methylcatechol + 9% methylhydroquinone
?
o-methoxyphenol + NADH + H+ + O2
4-methoxyresorcinol + 3-methoxycatechol + NAD+ + H2O
Q6Q8Q7; Q6Q8Q6; Q6Q8Q5; Q6Q8Q4; Q6Q8Q3; Q6Q8Q2
Substrates: -
Products: 87% 4-methoxyresorcinol, 11% 3-methoxycatechol, and 2% methoxyhydroquinone
Products: 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
Substrates: -
Products: 87% 4-methoxyresorcinol, 11% 3-methoxycatechol, and 2% methoxyhydroquinone
Products: 87% 4-methoxyresorcinol, 11% 3-methoxycatechol, and 2% methoxyhydroquinone
?
o-tyrosol + 2 NADH + 2 H+ + O2
2,3-dihydroxyphenylethanol + 2 NAD+ + 2 H2O
Substrates: -
Products: mutants I100A, I100S and I100G hydroxylate p-tyrosol to form 3,4-dihydroxyphenylethanol with 24%, 11% and 13% conversion, respectively, respectively
Products: 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
Substrates: -
Products: mutants I100A, I100S and I100G hydroxylate p-tyrosol to form 3,4-dihydroxyphenylethanol with 24%, 11% and 13% conversion, respectively, respectively
Products: 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
Substrates: -
Products: 83% 2,3-dihydroxyphenylethanol
Products: 83% 2,3-dihydroxyphenylethanol
?
o-tyrosol + NADH + H+ + O2
2,3-dihydroxyphenylethanol + NAD+ + H2O
Substrates: -
Products: 83% 2,3-dihydroxyphenylethanol
Products: 83% 2,3-dihydroxyphenylethanol
?
o-tyrosol + NADH + H+ + O2
2,3-dihydroxyphenylethanol + NAD+ + H2O
Substrates: reaction of mutant S395C, 18% conversion in 44 h
Products: -
Products: -
?
p-cresol + NADH + H+ + O2
4-methylcatechol + NAD+ + H2O
Q6Q8Q7; Q6Q8Q6; Q6Q8Q5; Q6Q8Q4; Q6Q8Q3; Q6Q8Q2
Substrates: -
Products: 100% 4-methylcatechol
Products: 100% 4-methylcatechol
?
p-cresol + NADH + H+ + O2
4-methylcatechol + NAD+ + H2O
Q6Q8Q7; Q6Q8Q6; Q6Q8Q5; Q6Q8Q4; Q6Q8Q3; Q6Q8Q2
Substrates: -
Products: 100% 4-methylcatechol
Products: 100% 4-methylcatechol
?
p-tyrosol + 2 NADH + 2 H+ + O2
3,4-dihydroxyphenylethanol + 2 NAD+ + 2 H2O
Substrates: -
Products: 10% 3,4-dihydroxyphenylethanol
Products: 10% 3,4-dihydroxyphenylethanol
?
p-tyrosol + 2 NADH + 2 H+ + O2
3,4-dihydroxyphenylethanol + 2 NAD+ + 2 H2O
Substrates: -
Products: 10% 3,4-dihydroxyphenylethanol
Products: 10% 3,4-dihydroxyphenylethanol
?
p-tyrosol + 2 NADH + 2 H+ + O2
3,4-dihydroxyphenylethanol + 2 NAD+ + 2 H2O
Substrates: -
Products: mutants I100A, I100S and I100G hydroxylate p-tyrosol to form 3,4-dihydroxyphenylethanol with 65%, 48% and 98% conversion, respectively, respectively
Products: 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
Substrates: -
Products: 63% m-tyrosol + 37% p-tyrosol
Products: 63% m-tyrosol + 37% p-tyrosol
?
phenylethanol + NADH + H+ + O2
m-tyrosol + p-tyrosol + NAD+ + H2O
Q6Q8Q7; Q6Q8Q6; Q6Q8Q5; Q6Q8Q4; Q6Q8Q3; Q6Q8Q2
Substrates: -
Products: 63% m-tyrosol + 37% p-tyrosol
Products: 63% m-tyrosol + 37% p-tyrosol
?
styrene + NADH + H+ + O2
styrene epoxide + NAD+ + H2O
Q6Q8Q7; Q6Q8Q6; Q6Q8Q5; Q6Q8Q4; Q6Q8Q3; Q6Q8Q2
Substrates: -
Products: -
Products: -
?
styrene + NADH + H+ + O2
styrene epoxide + NAD+ + H2O
Q6Q8Q7; Q6Q8Q6; Q6Q8Q5; Q6Q8Q4; Q6Q8Q3; Q6Q8Q2
Substrates: -
Products: -
Products: -
?
toluene + NADH + H+ + O2
4-methylphenol + NAD+ + H2O
Substrates: -
Products: -
Products: -
?
toluene + NADH + H+ + O2
4-methylphenol + NAD+ + H2O
Substrates: -
Products: -
Products: -
?
toluene + NADH + H+ + O2
4-methylphenol + NAD+ + H2O
Substrates: -
Products: -
Products: -
?
toluene + NADH + H+ + O2
4-methylphenol + NAD+ + H2O
Substrates: -
Products: -
Products: -
?
toluene + NADH + H+ + O2
4-methylphenol + NAD+ + H2O
Substrates: -
Products: -
Products: -
?
toluene + NADH + H+ + O2
4-methylphenol + NAD+ + H2O
Substrates: -
Products: 194% efficiency
Products: 194% efficiency
?
toluene + NADH + H+ + O2
4-methylphenol + NAD+ + H2O
Substrates: -
Products: 94% coupling
Products: 94% coupling
?
toluene + NADH + H+ + O2
4-methylphenol + NAD+ + H2O
Q6Q8Q7; Q6Q8Q6; Q6Q8Q5; Q6Q8Q4; Q6Q8Q3; Q6Q8Q2
Substrates: -
Products: 96% 4-methylphenol + 3% 3-methylphenol
Products: 96% 4-methylphenol + 3% 3-methylphenol
?
toluene + NADH + H+ + O2
4-methylphenol + NAD+ + H2O
Substrates: -
Products: 96% 4-methylphenol plus 2.8% 3-methylphenol plus 0.4% 2-methylphenol
Products: 96% 4-methylphenol plus 2.8% 3-methylphenol plus 0.4% 2-methylphenol
?
toluene + NADH + H+ + O2
4-methylphenol + NAD+ + H2O
Substrates: -
Products: 96% 4-methylphenol plus 2.8% 3-methylphenol plus 0.4% 2-methylphenol plus 0.8% benzyl alcohol
Products: 96% 4-methylphenol plus 2.8% 3-methylphenol plus 0.4% 2-methylphenol plus 0.8% benzyl alcohol
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toluene + NADH + H+ + O2
4-methylphenol + NAD+ + H2O
Substrates: -
Products: 96.2% 4-methylphenol, 1.5% 3-methylphenol, 0.9% 2-methylphenol, 1.4% benzyl alcohol
Products: 96.2% 4-methylphenol, 1.5% 3-methylphenol, 0.9% 2-methylphenol, 1.4% benzyl alcohol
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toluene + NADH + H+ + O2
4-methylphenol + NAD+ + H2O
Substrates: -
Products: -
Products: -
?
toluene + NADH + H+ + O2
4-methylphenol + NAD+ + H2O
Substrates: -
Products: 96% 4-methylphenol plus 2.8% 3-methylphenol plus 0.4% 2-methylphenol plus 0.8% benzyl alcohol
Products: 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
Substrates: -
Products: 194% efficiency
Products: 194% efficiency
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toluene + NADH + H+ + O2
4-methylphenol + NAD+ + H2O
Substrates: -
Products: -
Products: -
?
toluene + NADH + H+ + O2
4-methylphenol + NAD+ + H2O
Substrates: -
Products: 94% coupling
Products: 94% coupling
?
toluene + NADH + H+ + O2
4-methylphenol + NAD+ + H2O
Substrates: -
Products: -
Products: -
?
toluene + NADH + H+ + O2
4-methylphenol + NAD+ + H2O
Q6Q8Q7; Q6Q8Q6; Q6Q8Q5; Q6Q8Q4; Q6Q8Q3; Q6Q8Q2
Substrates: -
Products: 96% 4-methylphenol + 3% 3-methylphenol
Products: 96% 4-methylphenol + 3% 3-methylphenol
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toluene + NADH + H+ + O2
p-cresol + NAD+ + H2O
Substrates: -
Products: -
Products: -
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toluene + NADH + H+ + O2
p-cresol + NAD+ + H2O
Substrates: -
Products: -
Products: -
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additional information
?
-
Substrates: no substrates for wild-type: o-tyrosol, m-tyrosol, p-tyrosol
Products: -
Products: -
?
additional information
?
-
Substrates: no substrates for wild-type: o-tyrosol, m-tyrosol, p-tyrosol
Products: -
Products: -
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additional information
?
-
Substrates: 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
Products: -
Products: -
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additional information
?
-
Substrates: highly specific for para hydroxylation of toluene, o-xylene, m-xylene
Products: -
Products: -
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additional information
?
-
Substrates: no substrates for wild-type: o-tyrosol, m-tyrosol, p-tyrosol
Products: -
Products: -
?
additional information
?
-
Substrates: 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
Products: -
Products: -
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additional information
?
-
Substrates: highly specific for para hydroxylation of toluene, o-xylene, m-xylene
Products: -
Products: -
?
additional information
?
-
-
Substrates: highly specific for para hydroxylation of toluene, o-xylene, m-xylene
Products: -
Products: -
?
additional information
?
-
Substrates: no substrates for wild-type: o-tyrosol, m-tyrosol, p-tyrosol
Products: -
Products: -
?
additional information
?
-
Substrates: 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
Products: -
Products: -
?
additional information
?
-
Substrates: 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
Products: -
Products: -
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
Ferredoxin
ferredoxin binding leads to rearrangement of a loop about 30 A distal with a tightly matched, hydrogen bonded contact surface that places the [2Fe-2S] and diiron centres in their closest possible approach for electron transfer
-
iron-sulfur centre
complexes with phenolic products yield an asymmetric my-phenoxo-bridged diiron center and a shift of diiron ligand E231 into a hydrogen bonding position with conserved residue T201
iron-sulfur centre
component contains a Rieske ferredoxin centre. H-bonding to the Rieske [2Fe-2S] center involves four (H47, Q48, A66, and H67 of T4MOC) of the five backbone amide H-bonds expected, the fifth backbone amide (I50 of T4MOC) fails to exhibit a hyperfine shift
iron-sulfur centre
component T4MOC contains a Rieske-type iron-sulfur center
iron-sulfur centre
study of the Fe(II)Fe(II) active site in the hydroxylase component of toluene-4 monoxygenase and the complex of T4moH bound by its effector protein, T4moD. Binding of the effector protein changes the geometry of one iron center and orientation of its redox active orbital to accommodate the binding of O2 in a bridged structure for efficient 2-electron transfer that can form a peroxo intermediate
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Iron
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
phenylacetylene
-
selectively inhibits growth on toluene, but not on p-cresol, i.e. the toluene 4-monooxygenase pathway. Inhibition is irreversible
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.011
methyl 4-tolyl sulfide
whole-cell assay, 25°C, pH not specified in the publication
0.068
methyl 4-tolyl sulfide
whole-cell assay, 25°C, pH not specified in the publication
0.115
methyl phenyl sulfide
whole-cell assay, 25°C, pH not specified in the publication
0.129
methyl phenyl sulfide
whole-cell assay, 25°C, pH not specified in the publication
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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