1.14.12.11: toluene dioxygenase
This is an abbreviated version!
For detailed information about toluene dioxygenase, go to the full flat file.
Word Map on EC 1.14.12.11
-
1.14.12.11
-
putida
-
naphthalene
-
trichloroethylene
-
ethylbenzene
-
chlorobenzene
-
cis-dihydrodiols
-
dihydrodiols
-
cis-dihydroxylation
-
dot-t1e
-
ring-hydroxylating
-
cis-toluene
-
indene
-
cis-diols
-
pseudoalcaligenes
-
1-indanone
-
toluene-grown
-
3-methylcatechol
-
synthesis
-
analysis
-
degradation
- 1.14.12.11
- putida
- naphthalene
- trichloroethylene
- ethylbenzene
- chlorobenzene
- cis-dihydrodiols
- dihydrodiols
-
cis-dihydroxylation
- dot-t1e
-
ring-hydroxylating
-
cis-toluene
- indene
-
cis-diols
- pseudoalcaligenes
- 1-indanone
-
toluene-grown
- 3-methylcatechol
- synthesis
- analysis
- degradation
Reaction
Synonyms
ISPTOD, ISPTOL, More, oxygenase, toluene 2,3-di-, oxygenaseTOL, TDO, Tod, todC1C2BA, toluene 2,3-dioxygenase
ECTree
1.14.12.11 toluene dioxygenaseAdvanced search results
results (
results (Substrates Products
Substrates Products on EC 1.14.12.11 - toluene dioxygenase
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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
(+)-(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+
(+/-)-trans-2-phenyl-1-cyclohexanol + NADH + O2
3-(2-hydroxycyclohexanyl)-3,5-cyclohexadiene-1,2-diol + ?
-
-
-
?
(-)-(R)-indan-1-ol + NADH + O2
trans-(1R,3R)-1,3-dihydroxyindane + (-)-(1R,4R,5S)-1,4,5-trihydroxy-4,5-dihydroindane + NAD+
(1-methylcyclopropyl)benzene + NADH + H+ + O2
(1S,2R)-3-(1-methylcyclopropyl)cyclohexa-3,5-diene-1,2-diol + NAD+
(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+
(1R,2S)-(-)-trans-2-phenyl-1-cyclohexanol + NADH + O2
3-(2-hydroxycyclohexanyl)-3,5-cyclohexadiene-1,2-diol + ?
-
-
-
?
(4S,5S,6S)-4,5-dihydroxy-6-methoxycyclohex-2-enone + NADH + H+ + O2
(2S,3S,4S)-3,4-dihydroxy-2-methoxycyclohexanone + NAD+
(cis)-2-chloro-2-butene + NADH + O2
2-chloro-2-butene-1-ol + NAD+
-
12% of the activity with toluene
-
?
(R)-1-phenyl-1-ethanol + NADH + O2
3-[1(R)-hydroxyethyl]cyclohexa-3,5-diene-1(S),2(R)-diol + ?
-
-
-
?
(R)-2-phenylcyclohexanone + NADH + O2
(4S,4aR,9aR)-4,6,7,8,9,9a-hexahydro-4aH-dibenzofuran-4,5a-diol + ?
-
-
-
?
(S)-1-phenyl-1-ethanol + O2 + NADH + O2
3-[1(S)-hydroxyethyl]cyclohexa-3,5-diene-1(S),2(R)-diol + ?
-
-
-
?
(S)-2-phenylcyclohexanone + NADH + O2
(1S,5'S,6'R)-5',6'-dihydroxybicyclohexyl-1',3'-diene-2-one + ?
-
-
-
?
(trans)-2-chloro-2-butene + NADH + O2
?
-
4% of the activity with toluene
-
-
?
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+
1,1-dichloro-1-propene + NADH + O2
3,3-dichloro-2-propene-1-ol + NAD+
-
6% of the activity with toluene
-
?
1,1-dichloro-1-propene + NADH + O2
?
-
18% of the activity with toluene
-
-
?
1-bromo-2-ethylbenzene + NADH + H+ + O2
(1S,2R)-4-bromo-3-ethylcyclohexa-3,5-diene-1,2-diol + NAD+
1-bromo-3-ethylbenzene + NADH + H+ + O2
(1S,2R)-5-bromo-3-ethylcyclohexa-3,5-diene-1,2-diol + NAD+
1-bromo-4-cyclopropylbenzene + NADH + H+ + O2
(1R,2R)-3-bromo-6-cyclopropylcyclohexa-3,5-diene-1,2-diol + NAD+
1-bromo-4-ethylbenzene + NADH + H+ + O2
(1R,2R)-3-bromo-6-ethylcyclohexa-3,5-diene-1,2-diol + NAD+
1-bromo-4-propylbenzene + NADH + H+ + O2
(1R,2R)-3-bromo-6-propylcyclohexa-3,5-diene-1,2-diol + NAD+
1-chloro-2-ethylbenzene + NADH + H+ + O2
(1S,2R)-4-chloro-3-ethylcyclohexa-3,5-diene-1,2-diol + NAD+
1-chloro-2-methyl-1-propene + NADH + O2
2-chloro-2-butene-1-ol + NAD+
-
13% of the activity with toluene
-
?
1-chloro-3-ethylbenzene + NADH + H+ + O2
(1S,2R)-5-chloro-3-ethylcyclohexa-3,5-diene-1,2-diol + NAD+
-
-
-
-
?
1-chloro-3-propylbenzene + NADH + H+ + O2
(1S,2R)-5-chloro-3-propylcyclohexa-3,5-diene-1,2-diol + NAD+
-
-
-
-
?
1-chloro-4-ethylbenzene + NADH + H+ + O2
(1R,2R)-3-chloro-6-ethylcyclohexa-3,5-diene-1,2-diol + NAD+
-
-
-
-
?
1-chloro-4-propylbenzene + NADH + H+ + O2
(1R,2R)-3-chloro-6-propylcyclohexa-3,5-diene-1,2-diol + NAD+
-
-
-
-
?
1-ethyl-2-fluorobenzene + NADH + H+ + O2
(1S,2R)-3-ethyl-4-fluorocyclohexa-3,5-diene-1,2-diol + NAD+
-
-
-
-
?
1-ethyl-2-iodobenzene + NADH + H+ + O2
(1S,2R)-3-ethyl-4-iodocyclohexa-3,5-diene-1,2-diol + NAD+
-
-
-
-
?
1-ethyl-3-fluorobenzene + NADH + H+ + O2
(1S,2R)-3-ethyl-5-fluorocyclohexa-3,5-diene-1,2-diol + NAD+
-
-
-
-
?
1-ethyl-4-fluorobenzene + NADH + H+ + O2
(1R,2R)-3-ethyl-6-fluorocyclohexa-3,5-diene-1,2-diol + NAD+
-
-
-
-
?
1-ethyl-4-iodobenzene + NADH + H+ + O2
(1R,2R)-3-ethyl-6-iodocyclohexa-3,5-diene-1,2-diol + NAD+
-
-
-
-
?
1-fluoro-2-propylbenzene + NADH + H+ + O2
(1S,2R)-4-fluoro-3-propylcyclohexa-3,5-diene-1,2-diol + NAD+
-
-
-
-
?
1-fluoro-4-propylbenzene + NADH + H+ + O2
(1R,2R)-3-fluoro-6-propylcyclohexa-3,5-diene-1,2-diol + NAD+
-
-
-
-
?
1-phenylcyclohexene + NADH + O2
(1S,2R)-3-(1-cyclohexenyl)-3,5-cyclohexadiene-1,2-diol + ?
-
-
-
?
2,3-dichloro-1-propene + NADH + O2
2,3-dichloro-2-propene-1-ol + NAD+
-
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+
-
biotransformation with intact cells
-
?
2-bromoindane + O2 + NADH
(-)-cis-(1S,2R)-2-bromoindan-1-ol + (+)-trans-(1S,3S)-1,3-dihydroxy-2-bromoindane + NAD+
-
biotransformation with intact cells
-
?
2-carbamoylindane + O2 + NADH
(-)-cis-(1S,2R)-2-azoindan-1-ol + NAD+
-
biotransformation with intact cells
-
?
2-chloroindane + O2 + NADH
(-)-cis-(1S,2R)-2-chloroindan-1-ol + (+)-trans-(1R,2R)-2-chloroindan-1-ol + NAD+
-
biotransformation with intact cells
-
?
2-chloroindane + O2 + NADH
(-)-trans-(1S,3S)-1,3-dihydroxy-2-chloroindane + NAD+
-
biotransformation with intact cells
-
?
2-cresol + NADH + H+ + O2
(1S,2R)-3-methylcyclohexa-3,5-diene-1,2,4-triol + (2R)-6-methylcyclohexa-3,5-diene-1,1,2-triol + NAD+
2-iodoindane + O2 + NADH
(-)-cis-(1S,2R)-1,2-dihydroxyindane + (-)-(1R)-1-hydroxyindene + (+)-(1S,3S)-1,3-dihydroxy-2-iodoindane + NAD+
-
biotransformation with intact cells
-
-
?
2-methoxyindane + O2 + NADH
(-)-cis-(1S,2R)-2-methoxyindan-1-ol + (-)-trans-(1R,2R)-2-methoxyindan-1-ol + NAD+
-
biotransformation with intact cells
-
?
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+
-
biotransformation with intact cells
-
?
3,4-dichloro-1-butene + NADH + O2
3,4-dichlorobutane-1,2-diol + NAD+
-
23% of the activity with toluene
-
?
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+
3-(trifluoromethyl)benzene-1,2-diol + NADH + H+ + O2
(4R,5S)-4,5-dihydroxy-3-(trifluoromethyl)cyclohex-2-en-1-one + NAD+
3-cresol + NADH + H+ + O2
(1R,2S)-6-methylcyclohexa-3,5-diene-1,2,4-triol + (2S)-3-methylcyclohexa-3,5-diene-1,1,2-triol + NAD+
3-ethylbenzene-1,2-diol + NADH + H+ + O2
(4R,5S)-3-ethyl-4,5-dihydroxycyclohex-2-en-1-one + NAD+
3-iodobenzene-1,2-diol + NADH + H+ + O2
(4S,5S)-4,5-dihydroxy-3-iodocyclohex-2-en-1-one + NAD+
3-methoxyphenol + NADH + H+ + O2
(1S,2S)-6-methoxycyclohexa-3,5-diene-1,2,4-triol + (2S)-3-methoxycyclohexa-3,5-diene-1,1,2-triol + NAD+
3-methylbenzene-1,2-diol + NADH + H+ + O2
(4R,5S)-4,5-dihydroxy-3-methylcyclohex-2-en-1-one + NAD+
-
-
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 + ?
-
-
-
?
3-phenylphenol + NADH + H+ + O2
(2R,3S)-2,3-dihydro[1,1'-biphenyl]-2,3,5-triol + (2S)-[1,1'-biphenyl]-2,3,3(2H)-triol + NAD+
3-tert-butylbenzene-1,2-diol + NADH + H+ + O2
(4R,5S)-3-tert-butyl-4,5-dihydroxycyclohex-2-en-1-one + NAD+
-
-
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
-
?
4-cresol + NADH + H+ + O2
(1R,2R)-6-methylcyclohexa-3,5-diene-1,2,3-triol + (2S)-4-methylcyclohexa-3,5-diene-1,1,2-triol + NAD+
-
-
-
-
?
4-picoline + NADH + O2
3-hydroxy-4-picoline + ?
-
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
-
?
4-xylene + NADH + H+ + O2
4-xylenol + NAD+ + H2O
-
activity in strain 39/D
-
-
?
allyl 2-bromobenzoate + NADH + H+ + O2
prop-2-en-1-yl (3S,4S)-2-bromo-3,4-dihydroxycyclohexa-1,5-diene-1-carboxylate + allyl (5S,6R)-5,6-dihydroxy-2-bromocyclohex-1,3-dienecarboxylate + NAD+
-
-
-
-
?
allyl 2-chlorobenzoate + NADH + H+ + O2
prop-2-en-1-yl (3S,4S)-2-chloro-3,4-dihydroxycyclohexa-1,5-diene-1-carboxylate + allyl (5S,6R)-5,6-dihydroxy-2-chlorocyclohex-1,3-dienecarboxylate + NAD+
-
-
-
-
?
allyl 2-fluorobenzoate + NADH + H+ + O2
prop-2-en-1-yl (3S,4S)-2-fluoro-3,4-dihydroxycyclohexa-1,5-diene-1-carboxylate + allyl (5S,6R)-5,6-dihydroxy-2-fluorocyclohex-1,3-dienecarboxylate + NAD+
-
-
-
-
?
allyl 2-iodobenzoate + NADH + H+ + O2
prop-2-en-1-yl (3S,4S)-3,4-dihydroxy-2-iodocyclohexa-1,5-diene-1-carboxylate + allyl (5S,6R)-5,6-dihydroxy-2-iodocyclohex-1,3-dienecarboxylate + NAD+
-
-
-
-
?
biphenyl-2,3-diol + NADH + H+ + O2
(4R,5S)-4,5-dihydroxy-3-phenylcyclohex-2-en-1-one + NAD+
-
-
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
-
?
bromobenzene + NADH + H+ + O2
cis-(1S,2S)-3-bromocyclohexa-3,5-diene-1,2-diol + NAD+
-
-
-
-
?
butyl phenyl sulfide + NADH + O2
(R)-butyl phenyl sulfoxide + ?
-
-
more than 98% R-enantiomer
?
cis-1,2-dichloroethene + NADH + O2
?
-
12% of the activity with toluene
-
-
?
cis-1,4-dichloro-2-butene + NADH + O2
1,4-dichlorobutane-2,3-diol
-
18% of the activity with toluene
-
?
cis-1-bromo-1-propene + NADH + O2
?
-
11% of the activity with toluene
-
-
?
cis-1-chloro-1-propene + NADH + O2
?
-
5% of the activity with toluene
-
-
?
cis-2-pentene + NADH + O2
pentane-2,3-diol + NAD+
-
16% of the activity with toluene
-
?
cis-dibromoethene + NADH + O2
1,2-dibromoethane-1,2-diol + NAD+
-
13% of the activity with toluene
-
?
cyclopropylbenzene + NADH + H+ + O2
(1S,2R)-3-cyclopropylcyclohexa-3,5-diene-1,2-diol + NAD+
diphenylmethane + NADH + O2
(1S,2R)-3-benzylcyclohexa-3,5-diene-1,2-diol + ?
-
-
-
-
?
ethenyl phenyl sulfide + NADH + O2
(R)-ethenyl phenyl sulfoxide + ?
-
-
more than 98% R-enantiomer
?
ethyl 2-bromobenzoate + NADH + H+ + O2
ethyl (3S,4S)-2-bromo-3,4-dihydroxycyclohexa-1,5-diene-1-carboxylate + ethyl (5S,6R)-5,6-dihydroxy-2-bromocyclohex-1,3-dienecarboxylate + NAD+
-
-
-
-
?
ethyl 2-chlorobenzoate + NADH + H+ + O2
ethyl (3S,4S)-2-chloro-3,4-dihydroxycyclohexa-1,5-diene-1-carboxylate + ethyl (5S,6R)-5,6-dihydroxy-2-chlorocyclohex-1,3-dienecarboxylate + NAD+
-
-
-
-
?
ethyl 2-fluorobenzoate + NADH + H+ + O2
ethyl (3S,4S)-2-fluoro-3,4-dihydroxycyclohexa-1,5-diene-1-carboxylate + ethyl (5S,6R)-5,6-dihydroxy-2-fluorocyclohex-1,3-dienecarboxylate + NAD+
-
-
-
-
?
ethyl 2-iodobenzoate + NADH + H+ + O2
ethyl (3S,4S)-3,4-dihydroxy-2-iodocyclohex-1,5-dienecarboxylate + ethyl (5S,6R)-5,6-dihydroxy-2-iodocyclohex-1,3-dienecarboxylate + NAD+
-
-
-
-
?
ethyl phenyl sulfide + NADH + O2
(R)-ethyl phenyl sulfoxide
-
-
more than 98% R-enantiomer
?
ethylbenzene + NADH + H+ + O2
cis-2,3-dihydroxy-2,3-dihydroethylbenzene + NAD+
-
-
-
-
?
ethylbenzene + NADH + H+ + O2
ethylbenzene cis-dihydrodiol + NAD+
-
-
-
-
?
indan-1-ol + O2 + NADH
(-)-cis-(1S,2R)-1,2-dihydroxyindane + (-)-trans-(1R,2R)-1,2-dihydroxyindane + (-)-(2R)-2-hydroxyindan-1-one + NAD+
indan-2-ol + O2 + NADH
(-)-cis-(1S,2R)-1,2-dihydroxyindane + (-)-trans-(1R,2R)-1,2-dihydroxyindane + NAD+
-
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+
-
biotransformation with intact cells
-
?
indene + NADH + H+ + O2
cis-(1S, 2R)-indandiol + 1-indenol + 1-indanone + NAD+
-
-
-
-
?
indene + NADH + H+ + O2
cis-(1S,2R)-indandiol + (1S)-indenol + NAD+
-
-
-
-
?
indene + O2 + NADH
(-)-cis-(1S,2R)-dihydroxyindan + (+)-(1S)-indenol + ?
-
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
?
methoxymethyl phenyl sulfide + NADH + O2
(R)-methoxymethyl phenyl sulfoxide + ?
-
-
more than 98% R-enantiomer
?
methyl (2-pyridyl) sulfide + NADH + O2
(R)-methyl (2-pyridyl) sulfoxide + ?
-
-
more than 98% R-enantiomer
?
methyl (2-thienyl) sulfide + NADH + O2
(R)-methyl (2-thienyl) sulfoxide + ?
-
-
more than 98% R-enantiomer
?
methyl 2-bromobenzoate + NADH + H+ + O2
methyl (3S,4S)-2-bromo-3,4-dihydroxycyclohexa-1,5-diene-1-carboxylate + methyl (5S,6R)-2-bromo-5,6-dihydroxycyclohexa-1,3-diene-1-carboxylate + NAD+
-
-
-
-
?
methyl 2-chlorobenzoate + NADH + H+ + O2
methyl (3S,4S)-2-chloro-3,4-dihydroxycyclohexa-1,5-diene-1-carboxylate + methyl (5S,6R)-2-chloro-5,6-dihydroxycyclohexa-1,3-diene-1-carboxylate + NAD+
-
-
-
-
?
methyl 2-fluorobenzoate + NADH + H+ + O2
methyl (3S,4S)-2-fluoro-3,4-dihydroxycyclohexa-1,5-diene-1-carboxylate + methyl (5S,6R)-5,6-dihydroxy-2-fluorocyclohexa-1,3-dienecarboxylate + NAD+
-
-
-
-
?
methyl 2-iodobenzoate + NADH + H+ + O2
methyl (3S,4S)-3,4-dihydroxy-2-iodocyclohexa-1,5-diene-1-carboxylate + methyl (5S,6R)-5,6-dihydroxy-2-iodocyclohexa-1,3-diene-1-carboxylate + NAD+
-
-
-
-
?
methyl p-nitrophenyl sulfide + O2
methyl p-nitrophenyl sulfoxide
-
-
86% S-enantiomer
?
methyl p-tolyl sulfide + O2
cis-1,2-dihydroxy-3-methyl-6-methylthiocyclohexa-3,5-diene
-
-
-
?
n-propyl 2-bromobenzoate + NADH + H+ + O2
propyl (3S,4S)-2-bromo-3,4-dihydroxycyclohexa-1,5-diene-1-carboxylate + propyl (5S,6R)-2-bromo-5,6-dihydroxycyclohexa-1,3-diene-1-carboxylate + NAD+
-
-
-
-
?
n-propyl 2-chlorobenzoate + NADH + H+ + O2
propyl (3S,4S)-2-chloro-3,4-dihydroxycyclohexa-1,5-diene-1-carboxylate + propyl (5S,6R)-2-chloro-5,6-dihydroxycyclohexa-1,3-diene-1-carboxylate + NAD+
-
-
-
-
?
n-propyl 2-fluorobenzoate + NADH + H+ + O2
propyl (3S,4S)-2-fluoro-3,4-dihydroxycyclohexa-1,5-diene-1-carboxylate + n-propyl (5S,6R)-5,6-dihydroxy-2-fluorocyclohex-1,3-dienecarboxylate + NAD+
-
-
-
-
?
n-propyl 2-iodobenzoate + NADH + H+ + O2
propyl (3S,4S)-3,4-dihydroxy-2-iodocyclohexa-1,5-diene-1-carboxylate + propyl (5S,6R)-5,6-dihydroxy-2-iodocyclohexa-1,3-diene-1-carboxylate + NAD+
-
-
-
-
?
p-methoxyphenyl methyl sulfide + O2
p-methoxyphenyl methyl sulfoxide
-
-
32% S-enantiomer
?
phenol + NADH + H+ + O2
(1S,2R)-cyclohexa-3,5-diene-1,2,4-triol + (2S)-cyclohexa-3,5-diene-1,1,2-triol + NAD+
-
-
-
-
?
phenylcyclohexane + NADH + O2
(1S,2R)-3-(1-cyclohexyl)-3,5-cyclohexadiene-1,2-diol + ?
-
-
-
?
propargyl 2-bromobenzoate + NADH + H+ + O2
prop-2-yn-1-yl (3S,4S)-2-bromo-3,4-dihydroxycyclohexa-1,5-diene-1-carboxylate + propargyl (5S,6R)-5,6-dihydroxy-2-bromocyclohex-1,3-dienecarboxylate + NAD+
-
-
-
-
?
propargyl 2-chlorobenzoate + NADH + H+ + O2
prop-2-yn-1-yl (3S,4S)-2-chloro-3,4-dihydroxycyclohexa-1,5-diene-1-carboxylate + propargyl (5S,6R)-5,6-dihydroxy-2-chlorocyclohex-1,3-dienecarboxylate + NAD+
-
-
-
-
?
propargyl 2-fluorobenzoate + NADH + H+ + O2
prop-2-yn-1-yl (3S,4S)-2-fluoro-3,4-dihydroxycyclohexa-1,5-diene-1-carboxylate + propargyl (5S,6R)-5,6-dihydroxy-2-fluorocyclohex-1,3-dienecarboxylate + NAD+
-
-
-
-
?
propargyl 2-iodobenzoate + NADH + H+ + O2
prop-2-yn-1-yl (3S,4S)-3,4-dihydroxy-2-iodocyclohexa-1,5-diene-1-carboxylate + propargyl (5S,6R)-5,6-dihydroxy-2-iodocyclohex-1,3-dienecarboxylate + NAD+
-
-
-
-
?
propylbenzene + NADH + H+ + O2
(1S,2R)-3-propylcyclohexa-3,5-diene-1,2-diol + NAD+
-
-
-
-
?
propylbenzene + NADH + H+ + O2
cis-(1S,2R)-3-propylcyclohexa-3,5-diene-1,2-diol + cis-(1S,2R)-3-[(1R)-1-hydroxypropyl]cyclohexa-3,5-diene-1,2-diol + NAD+
-
-
-
-
?
styrene + NADH + H+ + O2
cis-2,3-dihydroxy-1-vinylcyclohexa-4,6-diene + (R)1-phenyl-1,2-ethanediol + NAD+
-
-
-
-
?
trans-1,4-dichloro-2-butene + NADH + O2
1,4-dichloro-2-butanone + NAD+
-
18% of the activity with toluene
-
?
trans-1-bromo-1-propene + NADH + O2
?
-
3% of the activity with toluene
-
-
?
trans-1-chloro-1-propene + NADH + O2
?
-
4% of the activity with toluene
-
-
?
trichloroethylene + NADH + O2
?
-
trichloroethylene degradation is mediated by the former degradation of toluene, benzene or cumene
-
-
?
trichloroethylene + O2 + NADPH
formate + glyoxylate + NADP+
-
-
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+
[(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+
-
-
-
-
ir
(+)-(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+
-
biotransformation with intact cells
-
?
(+)-(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+
-
biotransformation with intact cells
-
?
(-)-(R)-indan-1-ol + NADH + O2
trans-(1R,3R)-1,3-dihydroxyindane + (-)-(1R,4R,5S)-1,4,5-trihydroxy-4,5-dihydroindane + NAD+
-
biotransformation with intact cell
-
?
(-)-(R)-indan-1-ol + NADH + O2
trans-(1R,3R)-1,3-dihydroxyindane + (-)-(1R,4R,5S)-1,4,5-trihydroxy-4,5-dihydroindane + NAD+
-
biotransformation with intact cell
-
?
(1-methylcyclopropyl)benzene + NADH + H+ + O2
(1S,2R)-3-(1-methylcyclopropyl)cyclohexa-3,5-diene-1,2-diol + NAD+
-
-
-
-
ir
(1-methylcyclopropyl)benzene + NADH + H+ + O2
(1S,2R)-3-(1-methylcyclopropyl)cyclohexa-3,5-diene-1,2-diol + NAD+
-
-
-
-
ir
(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+
-
-
-
-
ir
(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+
-
-
-
-
ir
(4S,5S,6S)-4,5-dihydroxy-6-methoxycyclohex-2-enone + NADH + H+ + O2
(2S,3S,4S)-3,4-dihydroxy-2-methoxycyclohexanone + NAD+
-
-
-
-
?
(4S,5S,6S)-4,5-dihydroxy-6-methoxycyclohex-2-enone + NADH + H+ + O2
(2S,3S,4S)-3,4-dihydroxy-2-methoxycyclohexanone + NAD+
-
-
-
-
?
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+
-
-
-
-
ir
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+
-
-
-
-
ir
1,2-dibromobenzene + NADH + O2
(1S,2S)-3,4-dibromo-cyclohexa-3,5-diene-1,2-diol + NAD+
-
-
-
-
?
1,2-dibromobenzene + NADH + O2
(1S,2S)-3,4-dibromo-cyclohexa-3,5-diene-1,2-diol + NAD+
-
-
-
-
?
1,3-dibromobenzene + NADH + O2
(1S,2S)-2,4-dibromo-cyclohexa-3,5-diene-1,2-diol + NAD+
-
-
-
-
?
1,3-dibromobenzene + NADH + O2
(1S,2S)-2,4-dibromo-cyclohexa-3,5-diene-1,2-diol + NAD+
-
-
-
-
?
1,4-dibromobenzene + NADH + O2
(1S,2S)-1,4-dibromo-cyclohexa-3,5-diene-1,2-diol + NAD+
-
-
-
-
?
1,4-dibromobenzene + NADH + O2
(1S,2S)-1,4-dibromo-cyclohexa-3,5-diene-1,2-diol + NAD+
-
-
-
-
?
1-bromo-2-ethylbenzene + NADH + H+ + O2
(1S,2R)-4-bromo-3-ethylcyclohexa-3,5-diene-1,2-diol + NAD+
-
-
-
-
?
1-bromo-2-ethylbenzene + NADH + H+ + O2
(1S,2R)-4-bromo-3-ethylcyclohexa-3,5-diene-1,2-diol + NAD+
-
-
-
-
?
1-bromo-3-ethylbenzene + NADH + H+ + O2
(1S,2R)-5-bromo-3-ethylcyclohexa-3,5-diene-1,2-diol + NAD+
-
-
-
-
?
1-bromo-3-ethylbenzene + NADH + H+ + O2
(1S,2R)-5-bromo-3-ethylcyclohexa-3,5-diene-1,2-diol + NAD+
-
-
-
-
?
1-bromo-4-cyclopropylbenzene + NADH + H+ + O2
(1R,2R)-3-bromo-6-cyclopropylcyclohexa-3,5-diene-1,2-diol + NAD+
-
-
-
-
ir
1-bromo-4-cyclopropylbenzene + NADH + H+ + O2
(1R,2R)-3-bromo-6-cyclopropylcyclohexa-3,5-diene-1,2-diol + NAD+
-
-
-
-
ir
1-bromo-4-ethylbenzene + NADH + H+ + O2
(1R,2R)-3-bromo-6-ethylcyclohexa-3,5-diene-1,2-diol + NAD+
-
-
-
-
?
1-bromo-4-ethylbenzene + NADH + H+ + O2
(1R,2R)-3-bromo-6-ethylcyclohexa-3,5-diene-1,2-diol + NAD+
-
-
-
-
?
1-bromo-4-propylbenzene + NADH + H+ + O2
(1R,2R)-3-bromo-6-propylcyclohexa-3,5-diene-1,2-diol + NAD+
-
-
-
-
?
1-bromo-4-propylbenzene + NADH + H+ + O2
(1R,2R)-3-bromo-6-propylcyclohexa-3,5-diene-1,2-diol + NAD+
-
-
-
-
?
1-chloro-2-ethylbenzene + NADH + H+ + O2
(1S,2R)-4-chloro-3-ethylcyclohexa-3,5-diene-1,2-diol + NAD+
-
-
-
-
?
1-chloro-2-ethylbenzene + NADH + H+ + O2
(1S,2R)-4-chloro-3-ethylcyclohexa-3,5-diene-1,2-diol + NAD+
-
-
-
-
?
2-chloroaniline + NADH + H+ + O2
? + NAD+
-
degradation rates in decreasing order: 4-chloroaniline, 3-chloroaniline, 2-chloroaniline, 3,4-dichloroaniline
-
-
?
2-chloroaniline + NADH + H+ + O2
? + NAD+
-
degradation rates in decreasing order: 4-chloroaniline, 3-chloroaniline, 2-chloroaniline, 3,4-dichloroaniline
-
-
?
2-cresol + NADH + H+ + O2
(1S,2R)-3-methylcyclohexa-3,5-diene-1,2,4-triol + (2R)-6-methylcyclohexa-3,5-diene-1,1,2-triol + NAD+
-
poor substrate
-
-
?
2-cresol + NADH + H+ + O2
(1S,2R)-3-methylcyclohexa-3,5-diene-1,2,4-triol + (2R)-6-methylcyclohexa-3,5-diene-1,1,2-triol + NAD+
-
poor substrate
-
-
?
2-indanone + NADH + O2
(S)-2-hydroxy-1-indanone + NAD+
-
no reaction with 1-indanone
95% S-enantiomer, product is formed by incorporation of a single atom of molecular oxygen rather than by dioxygenation of enol tautomers of the ketone substrate
?
2-indanone + NADH + O2
(S)-2-hydroxy-1-indanone + NAD+
-
no reaction with 1-indanone
95% S-enantiomer, product is formed by incorporation of a single atom of molecular oxygen rather than by dioxygenation of enol tautomers of the ketone substrate
?
2-methoxyphenol + NADH + H+ + O2
(4S,5S)-4,5-dihydroxy-2-methoxycyclohex-2-enone + NAD+
-
-
-
-
?
2-methoxyphenol + NADH + H+ + O2
(4S,5S)-4,5-dihydroxy-2-methoxycyclohex-2-enone + NAD+
-
-
-
-
?
3,4-dichloroaniline + NADH + H+ + O2
? + NAD+
-
degradation rates in decreasing order: 4-chloroaniline, 3-chloroaniline, 2-chloroaniline, 3,4-dichloroaniline
-
-
?
3,4-dichloroaniline + NADH + H+ + O2
? + NAD+
-
degradation rates in decreasing order: 4-chloroaniline, 3-chloroaniline, 2-chloroaniline, 3,4-dichloroaniline
-
-
?
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+
-
-
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-(propan-2-yl)cyclohex-2-en-1-one, and triols, (1R,2S,4R)-6-(propan-2-yl)cyclohex-5-ene-1,2,4-triol, are obtained from biotransformation of the phenol parent compound in strain UV4 cultures
-
?
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+
-
-
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-(propan-2-yl)cyclohex-2-en-1-one, and triols, (1R,2S,4R)-6-(propan-2-yl)cyclohex-5-ene-1,2,4-triol, are obtained from biotransformation of the phenol parent compound in strain UV4 cultures
-
?
3-(trifluoromethyl)benzene-1,2-diol + NADH + H+ + O2
(4R,5S)-4,5-dihydroxy-3-(trifluoromethyl)cyclohex-2-en-1-one + NAD+
-
-
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-(trifluoromethyl)cyclohex-2-en-1-one, and triols, (1R,2S,4R)-6-(trifluoromethyl)cyclohex-5-ene-1,2,4-triol, are obtained from biotransformation of the phenol parent compound in strain UV4 cultures
-
?
3-(trifluoromethyl)benzene-1,2-diol + NADH + H+ + O2
(4R,5S)-4,5-dihydroxy-3-(trifluoromethyl)cyclohex-2-en-1-one + NAD+
-
-
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-(trifluoromethyl)cyclohex-2-en-1-one, and triols, (1R,2S,4R)-6-(trifluoromethyl)cyclohex-5-ene-1,2,4-triol, are obtained from biotransformation of the phenol parent compound in strain UV4 cultures
-
?
3-chloroaniline + NADH + H+ + O2
? + NAD+
-
degradation rates in decreasing order: 4-chloroaniline, 3-chloroaniline, 2-chloroaniline, 3,4-dichloroaniline
-
-
?
3-chloroaniline + NADH + H+ + O2
? + NAD+
-
degradation rates in decreasing order: 4-chloroaniline, 3-chloroaniline, 2-chloroaniline, 3,4-dichloroaniline
-
-
?
3-cresol + NADH + H+ + O2
(1R,2S)-6-methylcyclohexa-3,5-diene-1,2,4-triol + (2S)-3-methylcyclohexa-3,5-diene-1,1,2-triol + NAD+
-
-
-
-
?
3-cresol + NADH + H+ + O2
(1R,2S)-6-methylcyclohexa-3,5-diene-1,2,4-triol + (2S)-3-methylcyclohexa-3,5-diene-1,1,2-triol + NAD+
-
-
-
-
?
3-cresol + NADH + H+ + O2
?
-
activity in strain UV4formation of the corresponding cis-diol and catechol
-
-
?
3-cresol + NADH + H+ + O2
?
-
activity in strain UV4, 3-cresol is a better substrate than 2-cresol
-
-
?
3-ethylbenzene-1,2-diol + NADH + H+ + O2
(4R,5S)-3-ethyl-4,5-dihydroxycyclohex-2-en-1-one + NAD+
-
-
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-ethyl-4,5-dihydroxycyclohex-2-en-1-one, and triols, (1R,2S,4R)-6-ethylcyclohex-5-ene-1,2,4-triol, are obtained from biotransformation of the phenol parent compound in strain UV4 cultures
-
?
3-ethylbenzene-1,2-diol + NADH + H+ + O2
(4R,5S)-3-ethyl-4,5-dihydroxycyclohex-2-en-1-one + NAD+
-
-
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-ethyl-4,5-dihydroxycyclohex-2-en-1-one, and triols, (1R,2S,4R)-6-ethylcyclohex-5-ene-1,2,4-triol, are obtained from biotransformation of the phenol parent compound in strain UV4 cultures
-
?
3-iodobenzene-1,2-diol + NADH + H+ + O2
(4S,5S)-4,5-dihydroxy-3-iodocyclohex-2-en-1-one + NAD+
-
-
alkyl-substituted cyclohexenone cis-diols are formed as the most significant metabolites prior to extraction
-
?
3-iodobenzene-1,2-diol + NADH + H+ + O2
(4S,5S)-4,5-dihydroxy-3-iodocyclohex-2-en-1-one + NAD+
-
-
alkyl-substituted cyclohexenone cis-diols are formed as the most significant metabolites prior to extraction
-
?
3-methoxyphenol + NADH + H+ + O2
(1S,2S)-6-methoxycyclohexa-3,5-diene-1,2,4-triol + (2S)-3-methoxycyclohexa-3,5-diene-1,1,2-triol + NAD+
-
-
-
-
?
3-methoxyphenol + NADH + H+ + O2
(1S,2S)-6-methoxycyclohexa-3,5-diene-1,2,4-triol + (2S)-3-methoxycyclohexa-3,5-diene-1,1,2-triol + NAD+
-
-
-
-
?
3-methoxyphenol + NADH + H+ + O2
(4S,5S)-4,5-dihydroxy-3-methoxycyclohex-2-enone + NAD+
-
-
-
-
?
3-methoxyphenol + NADH + H+ + O2
(4S,5S)-4,5-dihydroxy-3-methoxycyclohex-2-enone + NAD+
-
-
-
-
?
3-phenylphenol + NADH + H+ + O2
(2R,3S)-2,3-dihydro[1,1'-biphenyl]-2,3,5-triol + (2S)-[1,1'-biphenyl]-2,3,3(2H)-triol + NAD+
-
-
-
-
?
3-phenylphenol + NADH + H+ + O2
(2R,3S)-2,3-dihydro[1,1'-biphenyl]-2,3,5-triol + (2S)-[1,1'-biphenyl]-2,3,3(2H)-triol + NAD+
-
-
-
-
?
4-chloroaniline + NADH + H+ + O2
4-chlorocatechol + 2-amino-5-chlorophenol + NAD+
-
-
-
-
?
4-chloroaniline + NADH + H+ + O2
4-chlorocatechol + 2-amino-5-chlorophenol + NAD+
-
degradation rates in decreasing order: 4-chloroaniline, 3-chloroaniline, 2-chloroaniline, 3,4-dichloroaniline
toluene dioxygenase catalyzes both 1,2- and 2,3-dioxygenation of 4-chloroaniline
-
?
4-chloroaniline + NADH + H+ + O2
4-chlorocatechol + 2-amino-5-chlorophenol + NAD+
-
degradation rates in decreasing order: 4-chloroaniline, 3-chloroaniline, 2-chloroaniline, 3,4-dichloroaniline
toluene dioxygenase catalyzes both 1,2- and 2,3-dioxygenation of 4-chloroaniline
-
?
4-chloroaniline + NADH + H+ + O2
4-chlorocatechol + 2-amino-5-chlorophenol + NAD+
-
-
-
-
?
benzene + NADH + O2
benzene dihydrodiol + NAD+
-
involved in the conversion of aromatic compounds to their corresponding catechols
-
-
?
bromobenzene + NADH + H+ + O2
(1S,2S)-3-bromocyclohexa-3,5-diene-1,2-diol + NAD+
-
-
-
-
?
bromobenzene + NADH + H+ + O2
(1S,2S)-3-bromocyclohexa-3,5-diene-1,2-diol + NAD+
-
-
-
-
?
chlorobenzene + NADH + H+ + O2
(1S,2S)-3-chlorocyclohexa-3,5-diene-1,2-diol + NAD+
-
-
-
-
?
chlorobenzene + NADH + H+ + O2
(1S,2S)-3-chlorocyclohexa-3,5-diene-1,2-diol + NAD+
-
-
-
-
?
cyclopropylbenzene + NADH + H+ + O2
(1S,2R)-3-cyclopropylcyclohexa-3,5-diene-1,2-diol + NAD+
-
-
-
-
ir
cyclopropylbenzene + NADH + H+ + O2
(1S,2R)-3-cyclopropylcyclohexa-3,5-diene-1,2-diol + NAD+
-
-
-
-
ir
ethylbenzene + NADH + O2
?
-
involved in the conversion of aromatic compounds to their corresponding catechols
-
-
?
indan-1-ol + O2 + NADH
(-)-cis-(1S,2R)-1,2-dihydroxyindane + (-)-trans-(1R,2R)-1,2-dihydroxyindane + (-)-(2R)-2-hydroxyindan-1-one + NAD+
-
biotransformation with intact cells
-
?
indan-1-ol + O2 + NADH
(-)-cis-(1S,2R)-1,2-dihydroxyindane + (-)-trans-(1R,2R)-1,2-dihydroxyindane + (-)-(2R)-2-hydroxyindan-1-one + NAD+
-
biotransformation with intact cells
-
?
indane + NADH + O2
(-)-(1R)-indanol + NAD+
-
monooxygenase reaction of toluene dioxygenase
84% enantiomeric excess of (-)-(1R)-indanol, 70% of the oxygen in 1-indanol is derived from water
?
indane + NADH + O2
(-)-(1R)-indanol + NAD+
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biotransformation with intact cells
+ indan-1-one
?
indane + NADH + O2
(-)-(1R)-indanol + NAD+
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biotransformation with intact cells
+ indan-1-one
?
indole + NADH + H+ + O2
2,2'-bis(2,3-dihydro-3-oxoindolyliden) + NAD+
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i.e. indigo
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?
indole + NADH + H+ + O2
2,2'-bis(2,3-dihydro-3-oxoindolyliden) + NAD+
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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
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?
iodobenzene + NADH + H+ + O2
(1S,2S)-3-iodocyclohexa-3,5-diene-1,2-diol + NAD+
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-
-
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?
iodobenzene + NADH + H+ + O2
(1S,2S)-3-iodocyclohexa-3,5-diene-1,2-diol + NAD+
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?
isopropyl phenyl sulfide + NADH + O2
(R)-isopropyl phenyl sulfoxide + ?
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more than 98% R-enantiomer
?
isopropyl phenyl sulfide + NADH + O2
(R)-isopropyl phenyl sulfoxide + ?
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more than 98% R-enantiomer
?
methyl phenyl sulfide + NADH + O2
(R)-methyl phenyl sulfoxide + ?
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more than 98% R-enantiomer
?
methyl phenyl sulfide + NADH + O2
(R)-methyl phenyl sulfoxide + ?
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more than 98% R-enantiomer
?
methyl phenyl sulfide + NADH + O2
(R)-methyl phenyl sulfoxide + ?
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more than 98% R-enantiomer
?
propyl phenyl sulfide + NADH + O2
(R)-propyl phenyl sulfoxide + ?
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more than 98% R-enantiomer
?
propyl phenyl sulfide + NADH + O2
(R)-propyl phenyl sulfoxide + ?
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more than 98% R-enantiomer
?
toluene + NADH + H+ + O2
(1S,2R)-3-methylcyclohexa-3,5-diene-1,2-diol + NAD+
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?
toluene + NADH + H+ + O2
(1S,2R)-3-methylcyclohexa-3,5-diene-1,2-diol + NAD+
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?
toluene + NADH + H+ + O2
(1S,2R)-3-methylcyclohexa-3,5-diene-1,2-diol + NAD+
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?
toluene + NADH + H+ + O2
(1S,2R)-3-methylcyclohexa-3,5-diene-1,2-diol + NAD+
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?
toluene + NADH + H+ + O2
(1S,2R)-3-methylcyclohexa-3,5-diene-1,2-diol + NAD+
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toluene + NADH + O2
(1S,2R)-3-methylcyclohexa-3,5-diene-1,2-diol + NAD+
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?
toluene + NADH + O2
(1S,2R)-3-methylcyclohexa-3,5-diene-1,2-diol + NAD+
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?
toluene + NADH + O2
(1S,2R)-3-methylcyclohexa-3,5-diene-1,2-diol + NAD+
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?
toluene + NADH + O2
(1S,2R)-3-methylcyclohexa-3,5-diene-1,2-diol + NAD+
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?
toluene + NADH + O2
(1S,2R)-3-methylcyclohexa-3,5-diene-1,2-diol + NAD+
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440335, 440336, 440337, 440338, 440339, 440340, 440341, 440342, 440343, 440344, 440345, 440346, 440347, 440348, 440349, 440350, 440351, 657604, 658332, 658336, 659826, 660044, 660050, 671081, 677654, 677655, 678835, 678837
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?
toluene + NADH + O2
(1S,2R)-3-methylcyclohexa-3,5-diene-1,2-diol + NAD+
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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 about 20% more activity towards toluene than the wild-type enzyme
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?
toluene + NADH + O2
(1S,2R)-3-methylcyclohexa-3,5-diene-1,2-diol + NAD+
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initial enzyme of toluene catabolism
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?
toluene + NADH + O2
(1S,2R)-3-methylcyclohexa-3,5-diene-1,2-diol + NAD+
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enzyme is involved in meta pathway for catechol degradation
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?
toluene + NADH + O2
(1S,2R)-3-methylcyclohexa-3,5-diene-1,2-diol + NAD+
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involved in the conversion of aromatic compounds to their corresponding catechols
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?
toluene + NADH + O2
(1S,2R)-3-methylcyclohexa-3,5-diene-1,2-diol + NAD+
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?
toluene + NADH + O2
(1S,2R)-3-methylcyclohexa-3,5-diene-1,2-diol + NAD+
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?
toluene + NADH + O2
(1S,2R)-3-methylcyclohexa-3,5-diene-1,2-diol + NAD+
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?
toluene + NADH + O2
(1S,2R)-3-methylcyclohexa-3,5-diene-1,2-diol + NAD+
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initial enzyme of toluene catabolism
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?
toluene + NADH + O2
(1S,2R)-3-methylcyclohexa-3,5-diene-1,2-diol + NAD+
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?
toluene + NADH + O2
(1S,2R)-3-methylcyclohexa-3,5-diene-1,2-diol + NAD+
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?
trifluoromethylbenzene + NADH + H+ + O2
(1S,2R)-3-(trifluoromethyl)cyclohexa-3,5-diene-1,2-diol + NAD+
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-
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?
trifluoromethylbenzene + NADH + H+ + O2
(1S,2R)-3-(trifluoromethyl)cyclohexa-3,5-diene-1,2-diol + NAD+
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?
xylene + NADH + O2
?
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involved in the conversion of aromatic compounds to their corresponding catechols
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?
additional information
?
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the oxygen atom in methyl phenyl sulfoxide is derived exclusively from dioxygen
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?
additional information
?
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the NADH-ferredoxinTOL reductase component catalyzes the NADH-dependent reduction of 2,6-dichloroindophenol, nitroblue tetrazolium and ferricyanide. NADPH is inactive
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additional information
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screening of substituted arenes containing remote chiral centers as substrates, enantiomers are indiscriminately processed to diastereomeric pairs
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additional information
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the purified alpha-subunit of oxygenase component is reduced by NADH and catalytic amounts of reductaseTOL and ferredoxinTOL. Reduced alpha-subunit can not oxidize toluene and catalysis is strictly dependent on the presence of beta-subunit
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additional information
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enzyme catalyzes monooxygenation and dioxygenation of aliphatic olefins
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additional information
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a high number of 2- or 3-substituted thiophenes were tested as substrates and were found to be metabolized
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additional information
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catechol and 3-methylcatechol are no substrates
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?
additional information
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the enzyme is organized in a multicomponent Rieske non-heme iron toluene 2,3-dioxygenase enzyme system. The TDO system is composed of a reductase, TDO-R, a Rieske [2Fe2S] ferredoxin, TDO-F, and a terminal dioxygenase, TDO-O, overview. TDO-F shuttles electrons from NADH via a flavin in TDO-R to TDO-O, which catalyzes the enantioselective addition of dioxygen to the aromatic nucleus to form cis-(1R,2S)-dihydroxy-3-methylcyclohexa-3,5-diene
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additional information
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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
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additional information
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enzyme active site structure, the orientation of the toluene substrate in the active site is consistent with the regiospecificity of oxygen incorporation seen in the product formed, overview
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additional information
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the dioxygenase catalyzes the formation of cyclohexenone cis-diols, and o-quinol dimers from phenols via cis-dihydrodiol intermediate, substrate specificity and formed products, stereospecificity, overview
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additional information
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TodT-P is the active form of the response regulator that induces RNA polymerase to transcribe from the PtodX promoter
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additional information
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toluene dioxygenase catalyzes the stereospecific synthesis of cis-dihydrodiol metabolites from 2-substituted naphthalene substrates, assignments of absolute configurations and conformations from circular dichroism and optical rotation measurements, overview
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additional information
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dioxygenase-catalysed cis-dihydroxylation of meta-substituted phenols to yield cyclohexenone cis-diol and derived enantiopure cis-triol metabolites, overview. Formation of enantiopure cyclohexenone cis-diol metabolites and binding interactions of the m-phenol substrates at the active site of toluene dioxygenase, overview. Product analysis by NMR
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?
additional information
?
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no activity with 3,5-dichloroaniline
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?
additional information
?
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a high number of 2- or 3-substituted thiophenes were tested as substrates and were found to be metabolized
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?
additional information
?
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toluene dioxygenase catalyzes the stereospecific synthesis of cis-dihydrodiol metabolites from 2-substituted naphthalene substrates, assignments of absolute configurations and conformations from circular dichroism and optical rotation measurements, overview
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?
additional information
?
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dioxygenase-catalysed cis-dihydroxylation of meta-substituted phenols to yield cyclohexenone cis-diol and derived enantiopure cis-triol metabolites, overview. Formation of enantiopure cyclohexenone cis-diol metabolites and binding interactions of the m-phenol substrates at the active site of toluene dioxygenase, overview. Product analysis by NMR
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