Information on EC 1.14.12.11 - toluene dioxygenase

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The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
1.14.12.11
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RECOMMENDED NAME
GeneOntology No.
toluene dioxygenase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
toluene + NADH + H+ + O2 = (1S,2R)-3-methylcyclohexa-3,5-diene-1,2-diol + NAD+
show the reaction diagram
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
oxidation
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redox reaction
reduction
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
Chloroalkane and chloroalkene degradation
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Microbial metabolism in diverse environments
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Toluene degradation
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toluene degradation to 2-oxopent-4-enoate (via toluene-cis-diol)
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SYSTEMATIC NAME
IUBMB Comments
toluene,NADH:oxygen oxidoreductase (1,2-hydroxylating)
A system, containing a reductase which is an iron-sulfur flavoprotein (FAD), an iron-sulfur oxygenase, and a ferredoxin. Some other aromatic compounds, including ethylbenzene, 4-xylene and some halogenated toluenes, are converted into the corresponding cis-dihydrodiols.
CAS REGISTRY NUMBER
COMMENTARY hide
120038-36-0
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
strain 4AK4
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Manually annotated by BRENDA team
strain 4AK4
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Manually annotated by BRENDA team
large oxygenase component
UniProt
Manually annotated by BRENDA team
large oxygenase component
UniProt
Manually annotated by BRENDA team
strain JM 109 (pDTG601)
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Manually annotated by BRENDA team
CFS215
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Manually annotated by BRENDA team
strain DOT-T1E
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Manually annotated by BRENDA team
strain KT2442
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Manually annotated by BRENDA team
NCIB11767
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Manually annotated by BRENDA team
strain TVA8
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Manually annotated by BRENDA team
strain W31
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Manually annotated by BRENDA team
strain W31
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Manually annotated by BRENDA team
strain 1317
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Manually annotated by BRENDA team
strain 1317
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Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
metabolism
physiological function
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(+)-(S)-indan-1-ol + O2 + NADH
(-)-(R)-indan-1-ol + indan-1-one + (+)-trans-(1S,3S)-1,3-dihydroxyindane + (-)-(3R)-3-hydroxyindan-1-one + NAD+
show the reaction diagram
(+/-)-trans-2-phenyl-1-cyclohexanol + NADH + O2
3-(2-hydroxycyclohexanyl)-3,5-cyclohexadiene-1,2-diol + ?
show the reaction diagram
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-
-
?
(-)-(R)-indan-1-ol + NADH + O2
trans-(1R,3R)-1,3-dihydroxyindane + (-)-(1R,4R,5S)-1,4,5-trihydroxy-4,5-dihydroindane + NAD+
show the reaction diagram
(1-methylcyclopropyl)benzene + NADH + H+ + O2
(1S,2R)-3-(1-methylcyclopropyl)cyclohexa-3,5-diene-1,2-diol + NAD+
show the reaction diagram
(1E)-prop-1-en-1-ylbenzene + NADH + H+ + O2
(1S,2R)-3-[(1E)-prop-1-en-1-yl]cyclohexa-3,5-diene-1,2-diol + NAD+
show the reaction diagram
(1R,2S)-(-)-trans-2-phenyl-1-cyclohexanol + NADH + O2
3-(2-hydroxycyclohexanyl)-3,5-cyclohexadiene-1,2-diol + ?
show the reaction diagram
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?
(cis)-2-chloro-2-butene + NADH + O2
2-chloro-2-butene-1-ol + NAD+
show the reaction diagram
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12% of the activity with toluene
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?
(R)-1-(2-pyridyl)ethanol + NADH + O2
(R)-1-(3-hydroxy-2-pyridyl)ethanol + NAD+
show the reaction diagram
(R)-1-phenyl-1-ethanol + NADH + O2
3-[1(R)-hydroxyethyl]cyclohexa-3,5-diene-1(S),2(R)-diol + ?
show the reaction diagram
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?
(R)-2-phenylcyclohexanone + NADH + O2
(4S,4aR,9aR)-4,6,7,8,9,9a-hexahydro-4aH-dibenzofuran-4,5a-diol + ?
show the reaction diagram
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?
(S)-1-(2-pyridyl)ethanol + NADH + O2
(S)-1-(3-hydroxy-2-pyridyl)ethanol + NAD+
show the reaction diagram
(S)-1-phenyl-1-ethanol + O2 + NADH + O2
3-[1(S)-hydroxyethyl]cyclohexa-3,5-diene-1(S),2(R)-diol + ?
show the reaction diagram
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?
(S)-2-phenylcyclohexanone + NADH + O2
(1S,5'S,6'R)-5',6'-dihydroxybicyclohexyl-1',3'-diene-2-one + ?
show the reaction diagram
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-
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?
(trans)-2-chloro-2-butene + NADH + O2
?
show the reaction diagram
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4% of the activity with toluene
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?
1,1'-(1S,2S)-cyclopropane-1,2-diyldibenzene + NADH + H+ + O2
(1S,2R)-3-[(1S,2S)-2-phenylcyclopropyl]cyclohexa-3,5-diene-1,2-diol + (1S,2R)-3-[(1R,2R)-2-phenylcyclopropyl]cyclohexa-3,5-diene-1,2-diol + NAD+
show the reaction diagram
1,1-dichloro-1-propene + NADH + O2
3,3-dichloro-2-propene-1-ol + NAD+
show the reaction diagram
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6% of the activity with toluene
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?
1,1-dichloro-1-propene + NADH + O2
?
show the reaction diagram
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18% of the activity with toluene
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?
1,2-dibromobenzene + NADH + O2
(1S,2S)-3,4-dibromo-cyclohexa-3,5-diene-1,2-diol + NAD+
show the reaction diagram
1,3-dibromobenzene + NADH + O2
(1S,2S)-2,4-dibromo-cyclohexa-3,5-diene-1,2-diol + NAD+
show the reaction diagram
1,4-dibromobenzene + NADH + O2
(1S,2S)-1,4-dibromo-cyclohexa-3,5-diene-1,2-diol + NAD+
show the reaction diagram
1-bromo-2-ethylbenzene + NADH + H+ + O2
(1S,2R)-4-bromo-3-ethylcyclohexa-3,5-diene-1,2-diol + NAD+
show the reaction diagram
1-bromo-3-ethylbenzene + NADH + H+ + O2
(1S,2R)-5-bromo-3-ethylcyclohexa-3,5-diene-1,2-diol + NAD+
show the reaction diagram
1-bromo-4-cyclopropylbenzene + NADH + H+ + O2
(1R,2R)-3-bromo-6-cyclopropylcyclohexa-3,5-diene-1,2-diol + NAD+
show the reaction diagram
1-bromo-4-ethylbenzene + NADH + H+ + O2
(1R,2R)-3-bromo-6-ethylcyclohexa-3,5-diene-1,2-diol + NAD+
show the reaction diagram
1-bromo-4-propylbenzene + NADH + H+ + O2
(1R,2R)-3-bromo-6-propylcyclohexa-3,5-diene-1,2-diol + NAD+
show the reaction diagram
1-chloro-2-ethylbenzene + NADH + H+ + O2
(1S,2R)-4-chloro-3-ethylcyclohexa-3,5-diene-1,2-diol + NAD+
show the reaction diagram
1-chloro-2-methyl-1-propene + NADH + O2
2-chloro-2-butene-1-ol + NAD+
show the reaction diagram
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13% of the activity with toluene
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?
1-chloro-3-ethylbenzene + NADH + H+ + O2
(1S,2R)-5-chloro-3-ethylcyclohexa-3,5-diene-1,2-diol + NAD+
show the reaction diagram
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?
1-chloro-3-propylbenzene + NADH + H+ + O2
(1S,2R)-5-chloro-3-propylcyclohexa-3,5-diene-1,2-diol + NAD+
show the reaction diagram
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?
1-chloro-4-ethylbenzene + NADH + H+ + O2
(1R,2R)-3-chloro-6-ethylcyclohexa-3,5-diene-1,2-diol + NAD+
show the reaction diagram
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?
1-chloro-4-propylbenzene + NADH + H+ + O2
(1R,2R)-3-chloro-6-propylcyclohexa-3,5-diene-1,2-diol + NAD+
show the reaction diagram
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?
1-ethyl-2-fluorobenzene + NADH + H+ + O2
(1S,2R)-3-ethyl-4-fluorocyclohexa-3,5-diene-1,2-diol + NAD+
show the reaction diagram
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?
1-ethyl-2-iodobenzene + NADH + H+ + O2
(1S,2R)-3-ethyl-4-iodocyclohexa-3,5-diene-1,2-diol + NAD+
show the reaction diagram
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?
1-ethyl-3-fluorobenzene + NADH + H+ + O2
(1S,2R)-3-ethyl-5-fluorocyclohexa-3,5-diene-1,2-diol + NAD+
show the reaction diagram
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?
1-ethyl-4-fluorobenzene + NADH + H+ + O2
(1R,2R)-3-ethyl-6-fluorocyclohexa-3,5-diene-1,2-diol + NAD+
show the reaction diagram
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?
1-ethyl-4-iodobenzene + NADH + H+ + O2
(1R,2R)-3-ethyl-6-iodocyclohexa-3,5-diene-1,2-diol + NAD+
show the reaction diagram
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?
1-fluoro-2-propylbenzene + NADH + H+ + O2
(1S,2R)-4-fluoro-3-propylcyclohexa-3,5-diene-1,2-diol + NAD+
show the reaction diagram
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?
1-fluoro-4-propylbenzene + NADH + H+ + O2
(1R,2R)-3-fluoro-6-propylcyclohexa-3,5-diene-1,2-diol + NAD+
show the reaction diagram
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?
1-indanone + NADH + O2
(S)-2-hydroxy-1-indanone + NAD+
show the reaction diagram
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?
1-phenylcyclohexene + NADH + O2
(1S,2R)-3-(1-cyclohexenyl)-3,5-cyclohexadiene-1,2-diol + ?
show the reaction diagram
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-
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?
2 4-chloroindole + 2 NADPH + 2 H+ + 3 O2
4,4'-dichloroindigo + 2 NADP+ + 4 H2O
show the reaction diagram
2 4-methylindole + 2 NADPH + 2 H+ + 3 O2
4,4'-dimethylindigo + 2 NADP+ + 4 H2O
show the reaction diagram
2 5-chloroindole + 2 H+ + 3 O2
(2E)-5-chloro-2-(5-chloro-3-oxo-1,3-dihydro-2H-indol-2-ylidene)-1,2-dihydro-3H-indol-3-one + 2 NAD+ + 4 H2O
show the reaction diagram
2 5-methoxyindole + 2 H+ + 3 O2
(2E)-5-methoxy-2-(5-methoxy-3-oxo-1,3-dihydro-2H-indol-2-ylidene)-1,2-dihydro-3H-indol-3-one + 2 NAD+ + 4 H2O
show the reaction diagram
2 5-methoxyindole + 2 NADPH + 2 H+ + 3 O2
5,5'-dimethoxyindigo + 2 NADP+ + 4 H2O
show the reaction diagram
2 5-methylindole + 2 H+ + 3 O2
(2E)-5-methyl-2-(5-methyl-3-oxo-1,3-dihydro-2H-indol-2-ylidene)-1,2-dihydro-3H-indol-3-one + 2 NAD+ + 4 H2O
show the reaction diagram
2 5-methylindole + 2 NADPH + 2 H+ + 3 O2
5,5'-dimethylindigo + 2 NADP+ + 4 H2O
show the reaction diagram
2 6-nitroindole + 2 H+ + 3 O2
(2E)-6-nitro-2-(6-nitro-3-oxo-1,3-dihydro-2H-indol-2-ylidene)-1,2-dihydro-3H-indol-3-one + 2 NAD+ + 4 H2O
show the reaction diagram
2 7-chloroindole + 2 NADPH + 2 H+ + 3 O2
7,7'-dichloroindigo + 2 NADP+ + 4 H2O
show the reaction diagram
2 7-methylindole + 2 H+ + 3 O2
(2E)-7-methyl-2-(7-methyl-3-oxo-1,3-dihydro-2H-indol-2-ylidene)-1,2-dihydro-3H-indol-3-one + 2 NAD+ + 4 H2O
show the reaction diagram
2 7-methylindole + 2 NADPH + 2 H+ + 3 O2
7,7'-dimethylindigo + 2 NADP+ + 4 H2O
show the reaction diagram
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?
2 indole + 2 NADH + 2 H+ + 3 O2
(2E)-2-(3-oxo-1,3-dihydro-2H-indol-2-ylidene)-1,2-dihydro-3H-indol-3-one + 2 NAD+ + 4 H2O
show the reaction diagram
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98.9% conversion yield
-
?
2 indole + 2 NADPH + 2 H+ + 3 O2
indigo + 2 NADP+ + 4 H2O
show the reaction diagram
2,3-dichloro-1-propene + NADH + O2
2,3-dichloro-2-propene-1-ol + NAD+
show the reaction diagram
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19% of the activity with toluene
-
?
2-acetoxyindane + O2 + NADH
indan-2-ol + (-)-cis-(1S,2R)-1,2-dihydroxyindane + (-)-trans-(1R,2R)-1,2-dihydroxyindane + (-)-(2R)-2-hydroxyindan-1-one + NAD+
show the reaction diagram
-
biotransformation with intact cells
-
?
2-bromoindane + O2 + NADH
(-)-cis-(1S,2R)-2-bromoindan-1-ol + (+)-trans-(1S,3S)-1,3-dihydroxy-2-bromoindane + NAD+
show the reaction diagram
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biotransformation with intact cells
-
?
2-carbamoylindane + O2 + NADH
(-)-cis-(1S,2R)-2-azoindan-1-ol + NAD+
show the reaction diagram
-
biotransformation with intact cells
-
?
2-chloroaniline + NADH + H+ + O2
? + NAD+
show the reaction diagram
2-chloroindane + O2 + NADH
(-)-cis-(1S,2R)-2-chloroindan-1-ol + (+)-trans-(1R,2R)-2-chloroindan-1-ol + NAD+
show the reaction diagram
-
biotransformation with intact cells
-
?
2-chloroindane + O2 + NADH
(-)-trans-(1S,3S)-1,3-dihydroxy-2-chloroindane + NAD+
show the reaction diagram
-
biotransformation with intact cells
-
?
2-chlorothiophene + NADH
?
show the reaction diagram
2-cresol + NADH + H+ + O2
?
show the reaction diagram
-
activity in strain UV4
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?
2-ethylpyridine + NADH + O2
(R)-1-(2-pyridyl)ethanol + NAD+
show the reaction diagram
2-ethylpyridine + NADH + O2
2-ethyl-3-hydroxypyridine + NAD+
show the reaction diagram
2-ethylthiophene + NADH
?
show the reaction diagram
2-hexene + NADH + O2
hexane-2,3-diol + NAD+
show the reaction diagram
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-
-
?
2-indanone + NADH + O2
(S)-2-hydroxy-1-indanone + NAD+
show the reaction diagram
2-iodoindane + O2 + NADH
(-)-cis-(1S,2R)-1,2-dihydroxyindane + (-)-(1R)-1-hydroxyindene + (+)-(1S,3S)-1,3-dihydroxy-2-iodoindane + NAD+
show the reaction diagram
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biotransformation with intact cells
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?
2-methoxyindane + O2 + NADH
(-)-cis-(1S,2R)-2-methoxyindan-1-ol + (-)-trans-(1R,2R)-2-methoxyindan-1-ol + NAD+
show the reaction diagram
-
biotransformation with intact cells
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?
2-methylindan + O2 + NADH
(-)-trans-(1R,3R)-1,3-dihydroxy-2-methylindane + (-)-cis-(2S,3R)-3-hydroxy-2-methylindan-1-one + (-)-cis-(1R,2R)-1-hydroxy-2-methylindane + (-)-(2R)-2-methyindan-1-one + NAD+
show the reaction diagram
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biotransformation with intact cells
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?
2-methylthiophene + NADH
?
show the reaction diagram
3,4-dichloro-1-butene + NADH + O2
3,4-dichlorobutane-1,2-diol + NAD+
show the reaction diagram
-
23% of the activity with toluene
-
?
3,4-dichloroaniline + NADH + H+ + O2
? + NAD+
show the reaction diagram
3-(propan-2-yl)benzene-1,2-diol + NADH + H+ + O2
(4R,5S)-4,5-dihydroxy-3-(propan-2-yl)cyclohex-2-en-1-one + NAD+
show the reaction diagram
3-(trifluoromethyl)benzene-1,2-diol + NADH + H+ + O2
(4R,5S)-4,5-dihydroxy-3-(trifluoromethyl)cyclohex-2-en-1-one + NAD+
show the reaction diagram
3-chloroaniline + NADH + H+ + O2
? + NAD+
show the reaction diagram
3-cresol + NADH + H+ + O2
?
show the reaction diagram
3-ethylbenzene-1,2-diol + NADH + H+ + O2
(4R,5S)-3-ethyl-4,5-dihydroxycyclohex-2-en-1-one + NAD+
show the reaction diagram
3-iodobenzene-1,2-diol + NADH + H+ + O2
(4S,5S)-4,5-dihydroxy-3-iodocyclohex-2-en-1-one + NAD+
show the reaction diagram
3-methylbenzene-1,2-diol + NADH + H+ + O2
(4R,5S)-4,5-dihydroxy-3-methylcyclohex-2-en-1-one + NAD+
show the reaction diagram
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-
alkyl-substituted cyclohexenone cis-diols are formed as the most significant metabolites prior to extraction
-
?
3-phenylcyclohexene + NADH + O2
(1S,2R)-3-(cyclohexenyl)-3,5-cyclohexadiene-1,2-diol + ?
show the reaction diagram
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-
-
?
3-tert-butylbenzene-1,2-diol + NADH + H+ + O2
(4R,5S)-3-tert-butyl-4,5-dihydroxycyclohex-2-en-1-one + NAD+
show the reaction diagram
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-
alkyl-substituted cyclohexenone cis-diols are formed as the most significant metabolites prior to extraction. In addition to the cyclohexenone cis-diols, (4R,5S)-3-tert-butyl-4,5-dihydroxycyclohex-2-en-1-one, and triols, (1R,2S,4R)-6-tert-butylcyclohex-5-ene-1,2,4-triol, are obtained from biotransformation of the phenol parent compound in strain UV4 cultures
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4-chloroaniline + NADH + H+ + O2
4-chlorocatechol + 2-amino-5-chlorophenol + NAD+
show the reaction diagram
4-ethylpyridine + NADH + O2
4-ethyl-3-hydroxypyridine + NAD+
show the reaction diagram
4-methylpyridine + NADH + O2
3-hydroxy-4-methylpyridine + NAD+
show the reaction diagram
-
-
-
-
?
4-picoline + NADH + O2
3-hydroxy-4-picoline + ?
show the reaction diagram
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E. coli expressed mutant enzyme TDO 2-B38, in which the wild-type stop codon is replaced with a codon encoding threonine, exhibits 5.6-times higher activity towards 4-picoline than the wild-type enzyme
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4-propylpyridine + NADH + O2
3-hydroxy-4-propylpyridine + NAD+
show the reaction diagram
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-
-
-
?
4-xylene + NADH + H+ + O2
4-xylenol + NAD+ + H2O
show the reaction diagram
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activity in strain 39/D
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-
?
5-cyanoindole + NADH + O2
?
show the reaction diagram
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-
-
-
?
5-nitroindole + NADH + O2
?
show the reaction diagram
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-
-
-
?
6-bromoindene + NADH + O2
6-bromoinden-1-ol + NAD+
show the reaction diagram
6-chloroindole + NADH + O2
?
show the reaction diagram
-
-
-
-
?
6-methoxyindole + NADH + O2
?
show the reaction diagram
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-
-
-
?
7-bromoindole + NADH + O2
?
show the reaction diagram
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-
-
-
?
7-chloroindole + NADH + O2
?
show the reaction diagram
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-
-
-
?
benzene + NADH + O2
benzene cis-dihydrodiol + NAD+
show the reaction diagram
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-
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-
?
benzene + NADH + O2
benzene dihydrodiol + NAD+
show the reaction diagram
biphenyl-2,3-diol + NADH + H+ + O2
(4R,5S)-4,5-dihydroxy-3-phenylcyclohex-2-en-1-one + NAD+
show the reaction diagram
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-
alkyl-substituted cyclohexenone cis-diols are formed as the most significant metabolites prior to extraction. In addition to the cyclohexenone cis-diols, (4R,5S)-4,5-dihydroxy-3-phenylcyclohex-2-en-1-one, and triols, (1R,2S,4R)-6-phenylcyclohex-5-ene-1,2,4-triol, are obtained from biotransformation of the phenol parent compound in strain UV4 cultures
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bromobenzene + NADH + H+ + O2
(1S,2S)-3-bromocyclohexa-3,5-diene-1,2-diol + NAD+
show the reaction diagram
butyl phenyl sulfide + NADH + O2
(R)-butyl phenyl sulfoxide + ?
show the reaction diagram
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-
more than 98% R-enantiomer
?
chlorobenzene + NADH + H+ + O2
(1S,2S)-3-chlorocyclohexa-3,5-diene-1,2-diol + NAD+
show the reaction diagram
chromane + NADH + O2
chromane-4-ol + chromane-4-one + NAD+
show the reaction diagram
cis-1,2-dichloroethene + NADH + H+ + O2
? + NAD+
show the reaction diagram
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-
-
-
?
cis-1,2-dichloroethene + NADH + O2
?
show the reaction diagram
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12% of the activity with toluene
-
-
?
cis-1,4-dichloro-2-butene + NADH + O2
1,4-dichlorobutane-2,3-diol
show the reaction diagram
-
18% of the activity with toluene
-
?
cis-1-bromo-1-propene + NADH + O2
?
show the reaction diagram
-
11% of the activity with toluene
-
-
?
cis-1-chloro-1-propene + NADH + O2
?
show the reaction diagram
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5% of the activity with toluene
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-
?
cis-2-heptene + NADH + O2
heptane-2,3-diol + NAD+
show the reaction diagram
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-
-
?
cis-2-octene + NADH + O2
octane-2,3-diol + NAD+
show the reaction diagram
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-
-
?
cis-2-pentene + NADH + O2
pentane-2,3-diol + NAD+
show the reaction diagram
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16% of the activity with toluene
-
?
cis-dibromoethene + NADH + O2
1,2-dibromoethane-1,2-diol + NAD+
show the reaction diagram
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13% of the activity with toluene
-
?
cumene + NADH + O2
?
show the reaction diagram
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-
-
-
?
cyclopropylbenzene + NADH + H+ + O2
(1S,2R)-3-cyclopropylcyclohexa-3,5-diene-1,2-diol + NAD+
show the reaction diagram
diphenylmethane + NADH + O2
(1S,2R)-3-benzylcyclohexa-3,5-diene-1,2-diol + ?
show the reaction diagram
-
-
-
-
?
ethenyl phenyl sulfide + NADH + O2
(R)-ethenyl phenyl sulfoxide + ?
show the reaction diagram
-
-
more than 98% R-enantiomer
?
ethyl phenyl sulfide + NADH + O2
(R)-ethyl phenyl sulfoxide
show the reaction diagram
-
-
more than 98% R-enantiomer
?
ethylbenzene + NADH + O2
?
show the reaction diagram
ethylbenzene + NADH + O2
cis-toluene dihydrodiol + NAD+
show the reaction diagram
-
-
-
-
?
ethylbenzene + NADH + O2
ethylbenzene cis-dihydrodiol + NAD+
show the reaction diagram
-
-
-
-
?
indan-1-ol + O2 + NADH
(-)-cis-(1S,2R)-1,2-dihydroxyindane + (-)-trans-(1R,2R)-1,2-dihydroxyindane + (-)-(2R)-2-hydroxyindan-1-one + NAD+
show the reaction diagram
indan-2-ol + O2 + NADH
(-)-cis-(1S,2R)-1,2-dihydroxyindane + (-)-trans-(1R,2R)-1,2-dihydroxyindane + NAD+
show the reaction diagram
-
biotransformation with intact cells
-
?
indan-2-one + O2 + NADH
indan-2-ol + (-)-cis-(1S,2R)-1,2-dihydroxy-indane + (-)-trans-(1R,2R)-1,2-dihydroxy-indane + NAD+
show the reaction diagram
-
biotransformation with intact cells
-
?
indane + NADH + O2
(-)-(1R)-indanol + NAD+
show the reaction diagram
indene + NADH + O2
cis-(1S, 2R)-indandiol + 1-indenol + 1-indanone + NAD+
show the reaction diagram
-
-
-
-
?
indene + NADH + O2
cis-1,2-dihydoxyindane + NAD+
show the reaction diagram
indene + O2 + NADH
(-)-cis-(1S,2R)-dihydroxyindan + (+)-(1S)-indenol + ?
show the reaction diagram
-
monooxygenase reaction of toluene dioxygenase
in addition the enzyme catalyzes the dioxygen addition of the nonaromatic double bond of indene to form cis-1,2-indanediol. The oxygen atom in 1-indenol and cis,1,2-indanediol is derived from molecular oxygen
?
indole + NADH + H+ + O2
2,2'-bis(2,3-dihydro-3-oxoindolyliden) + NAD+
show the reaction diagram
indole + NADH + O2
?
show the reaction diagram
-
-
-
-
?
indole + NADH + O2
indigo + NAD+
show the reaction diagram
-
-
-
-
?
indole + NADPH + H+ + O2
indigo + 2-(7-oxo-1H-indol-6(7H)-ylidene) indolin-3-one + NADP+
show the reaction diagram
-
-
98.8% transformation yield, 2-(7-oxo-1H-indol-6(7H)-ylidene) indolin-3-one is a purple product of the dimerization of isatin and 7-hydroxylindole at the C-2 and C-6 positions
-
?
iodobenzene + NADH + H+ + O2
(1S,2S)-3-iodocyclohexa-3,5-diene-1,2-diol + NAD+
show the reaction diagram
isopropyl phenyl sulfide + NADH + O2
(R)-isopropyl phenyl sulfoxide + ?
show the reaction diagram
methoxymethyl phenyl sulfide + NADH + O2
(R)-methoxymethyl phenyl sulfoxide + ?
show the reaction diagram
-
-
more than 98% R-enantiomer
?
methyl (2-pyridyl) sulfide + NADH + O2
(R)-methyl (2-pyridyl) sulfoxide + ?
show the reaction diagram
-
-
more than 98% R-enantiomer
?
methyl (2-thienyl) sulfide + NADH + O2
(R)-methyl (2-thienyl) sulfoxide + ?
show the reaction diagram
-
-
more than 98% R-enantiomer
?
methyl p-nitrophenyl sulfide + O2
methyl p-nitrophenyl sulfoxide
show the reaction diagram
-
-
86% S-enantiomer
?
methyl p-tolyl sulfide + O2
cis-1,2-dihydroxy-3-methyl-6-methylthiocyclohexa-3,5-diene
show the reaction diagram
-
-
-
?
methyl phenyl sulfide + NADH + O2
(R)-methyl phenyl sulfoxide + ?
show the reaction diagram
p-methoxyphenyl methyl sulfide + O2
p-methoxyphenyl methyl sulfoxide
show the reaction diagram
-
-
32% S-enantiomer
?
phenol + NADPH + H+ + O2
catechol + NADP+ + H2O
show the reaction diagram
phenylcyclohexane + NADH + O2
(1S,2R)-3-(1-cyclohexyl)-3,5-cyclohexadiene-1,2-diol + ?
show the reaction diagram
-
-
-
?
propyl phenyl sulfide + NADH + O2
(R)-propyl phenyl sulfoxide + ?
show the reaction diagram
propylbenzene + NADH + H+ + O2
(1S,2R)-3-propylcyclohexa-3,5-diene-1,2-diol + NAD+
show the reaction diagram
-
-
-
-
?
thiophene + NADH
?
show the reaction diagram
-
-
-
-
?
toluene + NADH + H+ + O2
(1S,2R)-3-methylcyclohexa-3,5-diene-1,2-diol + NAD+
show the reaction diagram
toluene + NADH + O2
(1S,2R)-3-methylcyclohexa-3,5-diene-1,2-diol + NAD+
show the reaction diagram
trans-1,4-dichloro-2-butene + NADH + O2
1,4-dichloro-2-butanone + NAD+
show the reaction diagram
-
18% of the activity with toluene
-
?
trans-1-bromo-1-propene + NADH + O2
?
show the reaction diagram
-
3% of the activity with toluene
-
-
?
trans-1-chloro-1-propene + NADH + O2
?
show the reaction diagram
-
4% of the activity with toluene
-
-
?
trans-dibromoethene + NADH + O2
?
show the reaction diagram
-
5% of the activity with toluene
-
-
?
trichloroethene + NADH + H+ + O2
? + NAD+
show the reaction diagram
-
-
-
-
?
trichloroethylene + NADH + O2
?
show the reaction diagram
-
trichloroethylene degradation is mediated by the former degradation of toluene, benzene or cumene
-
-
?
trichloroethylene + O2 + NADH
?
show the reaction diagram
trichloroethylene + O2 + NADPH
formate + glyoxylate + NADP+
show the reaction diagram
-
-
formate accounts for 47% of the trichloroethylene oxidized, glyoxylate accounts for 17% of the trichloroethylene oxidized. Both carbon atoms give rise to formic acid
?
trifluoromethylbenzene + NADH + H+ + O2
(1S,2R)-3-(trifluoromethyl)cyclohexa-3,5-diene-1,2-diol + NAD+
show the reaction diagram
xylene + NADH + O2
?
show the reaction diagram
[(1S,2S)-2-methylcyclopropyl]benzene + NADH + H+ + O2
(1S,2R)-3-[(1S,2S)-2-methylcyclopropyl]cyclohexa-3,5-diene-1,2-diol + (1S,2R)-3-[(1R,2R)-2-methylcyclopropyl]cyclohexa-3,5-diene-1,2-diol + NAD+
show the reaction diagram
-
-
-
-
ir
additional information
?
-
NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
2-cresol + NADH + H+ + O2
?
show the reaction diagram
-
activity in strain UV4
-
-
?
3-cresol + NADH + H+ + O2
?
show the reaction diagram
-
activity in strain UV4formation of the corresponding cis-diol and catechol
-
-
?
4-xylene + NADH + H+ + O2
4-xylenol + NAD+ + H2O
show the reaction diagram
-
activity in strain 39/D
-
-
?
benzene + NADH + O2
benzene dihydrodiol + NAD+
show the reaction diagram
-
involved in the conversion of aromatic compounds to their corresponding catechols
-
-
?
ethylbenzene + NADH + O2
?
show the reaction diagram
-
involved in the conversion of aromatic compounds to their corresponding catechols
-
-
?
indole + NADH + H+ + O2
2,2'-bis(2,3-dihydro-3-oxoindolyliden) + NAD+
show the reaction diagram
-
toluene dioxygenase is ubiquitous in nature and has a broad substrate range, including benzene, toluene, ethylbenzene and xylenes. The organism produces indigo from indole through the activity of TDO
i.e. indigo
-
?
toluene + NADH + O2
(1S,2R)-3-methylcyclohexa-3,5-diene-1,2-diol + NAD+
show the reaction diagram
xylene + NADH + O2
?
show the reaction diagram
-
involved in the conversion of aromatic compounds to their corresponding catechols
-
-
?
additional information
?
-
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
NADPH
[2Fe-2S]-center
-
the dinuclear iron (II) sites are coordinated by four carboxylates and two histidine residues: Fe1 is coordinated by His139, Glu106 and Glu136, Fe2 is coordinated by His234, Glu231 and Glu197
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
acetate
-
inhibits by hindering the tod gene expression
ethanol
phenol
-
competitive inhibition
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
5.429
phenol
-
pH 8.0, temperature not specified in the publication
additional information
additional information
-
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
2137
phenol
Arthrobacter sp.
-
pH 8.0, temperature not specified in the publication
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.045
-
with benzene as substrate
0.054
-
with ethylbenzene as substrate
0.056
-
with toluene as substrate
2.46
-
units per mg of alpha-subunit of oxygenase
additional information
-
-
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6.6 - 7.5
-
NADH-ferredoxinTOL reductase component
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
28
-
in vivo assay at
TEMPERATURE RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
40 - 60
-
-
pI VALUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7.8
-
about, TodT
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
14700
-
ferredoxinTOL component of the toluene dioxygenase, equilibrium sedimentation
15300
-
alpha2beta2, 2 * 46000 + 2 * 15300, oxygenase component of toluene dioxygenase
15500
-
1 * 15500, ferredoxinTOL component of the toluene dioxygenase, SDS-PAGE
20800
-
x * 52500 + x * 20800, oxygenase component, SDS-PAGE
22000
x * 49000, x * 46000, and x * 22000, SDS-PAGE, corresponding to alpha-subunit NagAc, large subunit of salicylate 5-hydroxylaseNagG and beta-subunit of the oxygenase
28000
-
phosphorylated TodT, gel filtration
46500
-
NADH-ferredoxinTOL reductase component, gel filtration
49000
x * 49000, x * 46000, and x * 22000, SDS-PAGE, corresponding to alpha-subunit NagAc, large subunit of salicylate 5-hydroxylaseNagG and beta-subunit of the oxygenase
52500
-
x * 52500 + x * 20800, oxygenase component, SDS-PAGE
108000
-
TodS
151000
-
oxygenase component, gel filtration
additional information
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
hexamer
-
enzyme is a heterohexamer containing a catalytic and a structural subunit type, consists of three domains: an FAD-binding domain, an NADH-binding domain and a C-terminal domain
monomer
tetramer
-
alpha2beta2, 2 * 46000 + 2 * 15300, oxygenase component of toluene dioxygenase
additional information
POSTTRANSLATIONAL MODIFICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
phosphoprotein
-
TodS exhibits basal autophosphorylation activity that increases in the presence of toluene and is translated as an increase in the rate of transphosphorylation of TodT, TodT phosphorylation occurs only with the folded protein by the TodS sensor kinase, binding site analysis, overview
Crystallization/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
homology modeling of the catalytic domain. The dinuclear iron (II) sites are coordinated by four carboxylates and two histidine residues: Fe1 is coordinated by His139, Glu106 and Glu136, Fe2 is coordinated by His234, Glu231 and Glu197
-
hanging drop and sitting drop vapour diffusion method using 40% (w/v) polyethylene glycol 600, 0.1 M sodium citrate pH 6.1 and 20-50 mM Fe(NH4)2(SO4)
-
purified recombinant enzyme system components, hanging-drop or sitting-drop vapour diffusion method, from 1.4 M ammonium sulfate, 0.1 M HEPES, pH 7.7. TDO-F crystallized in 38% PEG 8000, 0.1 M MES pH 6.1 or 37% PEG 8000, 0.1 M MES, pH 5.8. Apo-TDO-O crystallizes in 40% w/v PEG 600, 0.1 M sodium citrate, pH 5.8. Cocrystallization experiments with Fe(NH4)2(SO4)2 and toluene were performed under strict anaerobic conditions in 40% w/v PEG 600, 0.1 M sodium citrate pH 6.1, 20-50 mM Fe(NH4)2(SO4)2 and 20 mM toluene, X-ray diffraction structure determinhation and analysis at 1.2-3.2 A resolution, molecular replacement, structure modelling, overview
-
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-20C, ferredoxinTOL component of the toluene dioxygenase, stable for over 10 weeks
-
-20C, purified NADH-ferredoxinTOL reductase component is stable for two weeks
-
0-4C, ferredoxinTOL component of the toluene dioxygenase, stable for up to 72 h
-
0-4C, purified NADH-ferredoxinTOL reductase component is stable for up to 30 h
-
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
beta-subunit of oxygenase component
-
ferredoxinTOL component of the toluene dioxygenase
-
ferredoxinTOL component of the toluene dioxygenase; NADH-ferredoxinTOL reductase component of toluene dioxygenase; oxygenase component, ISPTOL
-
NADH-ferredoxinTOL reductase component of toluene dioxygenase
-
oxygenase component, ISPTOL
-
Q-Sepharose FF column chromatography
-
rapid purification of oxygenase component from a polyol-responsive monoclonal antibody
-
recombinant alpha-subunit of the oxygenase component
-
recombinant TDO-F, TDO-R, TDO-O and apo-TDO-O from Escherichia coli
-
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
cloned and expressed in Escherichia coli HB101
-
co-overexpression of TDO-F, TDO-R, TDO-O and apo-TDO-O in Escherichia coli
-
expressed in Escherichia coli
-
expressed in Escherichia coli DHalpha
-
expressed in Escherichia coli JM109; expressed in Escherichia coli strain JM109
-
expressed in Escherichia coli strain CGSC7692 (pDTG601A)
-
expression in Escherichia coli
expression of genes encoding toluene dioxygenase complex todC1C2BA in Escherichia coli
-
expression of mutant enzyme TDO 2-B38, in which the wild-type stop codon is replaced with a codon encoding Thr
-
expression of wild-type TodT, C-terminal part of TodT, and TodT mutants in Escherichia coli strain BL21(DE3). Genes todS and todT are transcribed from a single promoter called PtodX once the response regulator TodT is phosphorylated by the TodS sensor kinase in response to pathway substrates
-
genes encoding the three components of the toluene dioxygenase overproduced in Escherichia coli JM109: 1. the reductaseTOL - tolA, 2. the ferredoxinTOL and 3. the two subunits of the terminal dioxygenase - todC1C2
-
genes todC1C2BA, expression of the enzyme components todC1, C2, B, and A in Escherichia coli strain JM109 and in Rhodococcus opacus strain B-4. In Escherichia coli JM109, the yield of hydroxylated monoaromatics decreased with increasing substrate hydrophobicity, while in Rhodococcus opacus B-4, high performance in the hydroxylation of monoaromatics occurs, irrespective of substrate hydrophobicity.
-
EXPRESSION
ORGANISM
UNIPROT
LITERATURE
the todST operon is transcribed from a main promoter and that the +1 initiation point is located 31 nucleotides upstream from the A of the first ATG codon and is preceded by a -10/-35 canonical promoter. Expression from PtodS is under catabolite control, and in cells growing with glucose, the level of expression from this promoter is reduced, which in turn translates to low levels of the TodS/TodT regulators and results in a decrease of transcription from the PtodX promoter. The main underlying regulatory mechanisms of the tod structural genes are at the levels of catabolite repression control from PtodS and transcription activation, mediated by the TodT response regulator through a regulatory cascade in which the effector enhances autophosphorylation of TodS by ATP, with subsequent transphosphorylation of TodT
-
ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
D219A
-
mutation at alpha-subunit of oxygenase component completely abolishes toluene dioxygenase activity, mutation completely eliminates formation of cis-toluene dihydrodiol
E214A
-
mutation at alpha-subunit of oxygenase component completely abolishes toluene dioxygenase activity, mutation completely eliminates formation of cis-toluene dihydrodiol
E609L
-
increased activity with all substrates
H222A
-
mutation at alpha-subunit of oxygenase component completely abolishes toluene dioxygenase activity, mutation completely eliminates formation of cis-toluene dihydrodiol
H228A
-
mutation at alpha-subunit of oxygenase component completely abolishes toluene dioxygenase activity, mutation completely eliminates formation of cis-toluene dihydrodiol
Y221A
-
mutation at alpha-subunit of oxygenase component, 42% of the activity of the wild-type enzyme, formation of cis-toluene dihydrodiol is reduced
Y266A
-
mutation at alpha-subunit of oxygenase component, 12% of the activity of the wild-type enzyme, formation of cis-toluene dihydrodiol is reduced
additional information
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
analysis
-
whole cell bioassay for the detection of benzene, toluene, ethyl benzene, and xylenes (BTEX)
degradation
-
stable isotopes could serve as a diagnostic for detecting aerobic biodegradation of TCE by toluene oxygenases at contaminated sites. There are no significant differences in fractionation among the enzymes toluene 3-monoxygenase, toluene 4-monooxygenase, and toluene 2,3-dioxygenase for compounds trichloroethene and cis-1,2-dichloroethene
synthesis