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

Reaction

Toluene
+
NADH
+
H+
+
O2
=
(1S,2R)-3-Methylcyclohexa-3,5-diene-1,2-diol
+
NAD+

Synonyms

ISPTOD, ISPTOL, More, oxygenase, toluene 2,3-di-, oxygenaseTOL, TDO, Tod, todC1C2BA, toluene 2,3-dioxygenase

ECTree

     1 Oxidoreductases
         1.14 Acting on paired donors, with incorporation or reduction of molecular oxygen
             1.14.12 With NADH or NADPH as one donor, and incorporation of two atoms of oxygen into the other donor
                1.14.12.11 toluene dioxygenase

Substrates Products

Substrates Products on EC 1.14.12.11 - toluene dioxygenase

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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
-
-
-
?
(-)-(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
-
-
-
?
(4S,5S,6S)-4,5-dihydroxy-6-methoxycyclohex-2-enone + NADH + H+ + O2
(2S,3S,4S)-3,4-dihydroxy-2-methoxycyclohexanone + NAD+
show the reaction diagram
(cis)-2-chloro-2-butene + NADH + O2
2-chloro-2-butene-1-ol + NAD+
show the reaction diagram
-
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 + ?
show the reaction diagram
-
-
-
?
(R)-2-phenylcyclohexanone + NADH + O2
(4S,4aR,9aR)-4,6,7,8,9,9a-hexahydro-4aH-dibenzofuran-4,5a-diol + ?
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
-
-
-
?
(S)-2-phenylcyclohexanone + NADH + O2
(1S,5'S,6'R)-5',6'-dihydroxybicyclohexyl-1',3'-diene-2-one + ?
show the reaction diagram
-
-
-
?
(trans)-2-chloro-2-butene + NADH + O2
?
show the reaction diagram
-
4% of the activity with toluene
-
0
?
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
-
6% of the activity with toluene
-
?
1,1-dichloro-1-propene + NADH + O2
?
show the reaction diagram
-
18% of the activity with toluene
-
0
?
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
1,3-dinitrobenzene + NADH + H+ + O2
?
show the reaction diagram
-
-
-
0
?
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
-
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+
show the reaction diagram
-
-
-
0
?
1-chloro-3-propylbenzene + NADH + H+ + O2
(1S,2R)-5-chloro-3-propylcyclohexa-3,5-diene-1,2-diol + NAD+
show the reaction diagram
-
-
-
0
?
1-chloro-4-ethylbenzene + NADH + H+ + O2
(1R,2R)-3-chloro-6-ethylcyclohexa-3,5-diene-1,2-diol + NAD+
show the reaction diagram
-
-
-
0
?
1-chloro-4-propylbenzene + NADH + H+ + O2
(1R,2R)-3-chloro-6-propylcyclohexa-3,5-diene-1,2-diol + NAD+
show the reaction diagram
-
-
-
0
?
1-ethyl-2-fluorobenzene + NADH + H+ + O2
(1S,2R)-3-ethyl-4-fluorocyclohexa-3,5-diene-1,2-diol + NAD+
show the reaction diagram
-
-
-
0
?
1-ethyl-2-iodobenzene + NADH + H+ + O2
(1S,2R)-3-ethyl-4-iodocyclohexa-3,5-diene-1,2-diol + NAD+
show the reaction diagram
-
-
-
0
?
1-ethyl-3-fluorobenzene + NADH + H+ + O2
(1S,2R)-3-ethyl-5-fluorocyclohexa-3,5-diene-1,2-diol + NAD+
show the reaction diagram
-
-
-
0
?
1-ethyl-4-fluorobenzene + NADH + H+ + O2
(1R,2R)-3-ethyl-6-fluorocyclohexa-3,5-diene-1,2-diol + NAD+
show the reaction diagram
-
-
-
0
?
1-ethyl-4-iodobenzene + NADH + H+ + O2
(1R,2R)-3-ethyl-6-iodocyclohexa-3,5-diene-1,2-diol + NAD+
show the reaction diagram
-
-
-
0
?
1-fluoro-2-propylbenzene + NADH + H+ + O2
(1S,2R)-4-fluoro-3-propylcyclohexa-3,5-diene-1,2-diol + NAD+
show the reaction diagram
-
-
-
0
?
1-fluoro-4-propylbenzene + NADH + H+ + O2
(1R,2R)-3-fluoro-6-propylcyclohexa-3,5-diene-1,2-diol + NAD+
show the reaction diagram
-
-
-
0
?
1-indanone + NADH + O2
(S)-2-hydroxy-1-indanone + NAD+
show the reaction diagram
-
-
-
0
?
1-phenylcyclohexene + NADH + O2
(1S,2R)-3-(1-cyclohexenyl)-3,5-cyclohexadiene-1,2-diol + ?
show the reaction diagram
-
-
-
?
2,3-dichloro-1-propene + NADH + O2
2,3-dichloro-2-propene-1-ol + NAD+
show the reaction diagram
-
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
-
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
?
show the reaction diagram
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
(1S,2R)-3-methylcyclohexa-3,5-diene-1,2,4-triol + (2R)-6-methylcyclohexa-3,5-diene-1,1,2-triol + NAD+
show the reaction diagram
2-cresol + NADH + H+ + O2
?
show the reaction diagram
-
activity in strain UV4
-
0
?
2-ethylthiophene + NADH
?
show the reaction diagram
2-hexene + NADH + O2
hexane-2,3-diol + NAD+
show the reaction diagram
-
-
-
?
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
-
biotransformation with intact cells
-
0
?
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
-
?
2-methoxyphenol + NADH + H+ + O2
(4S,5S)-4,5-dihydroxy-2-methoxycyclohex-2-enone + NAD+ 10
show the reaction diagram
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
-
biotransformation with intact cells
-
?
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
?
show the reaction diagram
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
?
show the reaction diagram
-
-
-
0
?
3-chloroaniline + NADH + H+ + O2
? + NAD+
show the reaction diagram
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+
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-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+
show the reaction diagram
3-methoxyphenol + NADH + H+ + O2
(4S,5S)-4,5-dihydroxy-3-methoxycyclohex-2-enone + 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
-
-
alkyl-substituted cyclohexenone cis-diols are formed as the most significant metabolites prior to extraction
0
?
3-phenylcyclohexene + NADH + O2
(1S,2R)-3-(cyclohexenyl)-3,5-cyclohexadiene-1,2-diol + ?
show the reaction diagram
-
-
-
?
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+
show the reaction diagram
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
-
-
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
0
?
4-chloroaniline + NADH + H+ + O2
4-chlorocatechol + 2-amino-5-chlorophenol + NAD+
show the reaction diagram
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+
show the reaction diagram
-
-
-
0
?
4-picoline + NADH + O2
3-hydroxy-4-picoline + ?
show the reaction diagram
-
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
show the reaction diagram
-
activity in strain 39/D
-
0
?
5-cyanoindole + NADH + O2
?
show the reaction diagram
-
-
-
0
?
5-nitroindole + NADH + O2
?
show the reaction diagram
-
-
-
0
?
6-bromoindene + NADH + O2
6-bromoinden-1-ol + NAD+
show the reaction diagram
6-chloroindole + NADH + O2
?
show the reaction diagram
-
-
-
0
?
6-methoxyindole + NADH + O2
?
show the reaction diagram
-
-
-
0
?
7-bromoindole + NADH + O2
?
show the reaction diagram
-
-
-
0
?
7-chloroindole + NADH + O2
?
show the reaction diagram
-
-
-
0
?
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+
show the reaction diagram
-
-
-
0
?
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+
show the reaction diagram
-
-
-
0
?
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+
show the reaction diagram
-
-
-
0
?
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+
show the reaction diagram
-
-
-
0
?
benzaldoxime + NADH + H+ + O2
?
show the reaction diagram
-
-
-
0
?
benzamide iminol + NADH + H+ + O2
?
show the reaction diagram
-
-
-
0
?
benzene + NADH + O2
benzene cis-dihydrodiol + NAD+
show the reaction diagram
-
-
-
0
?
benzene + NADH + O2
benzene dihydrodiol + NAD+
show the reaction diagram
benzyl azide + NADH + H+ + O2
benzonitrile + NAD+ + ?
show the reaction diagram
-
-
-
0
?
biphenyl-2,3-diol + NADH + H+ + O2
(4R,5S)-4,5-dihydroxy-3-phenylcyclohex-2-en-1-one + NAD+
show the reaction diagram
-
-
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
0
?
bromobenzene + NADH + H+ + O2
(1S,2S)-3-bromocyclohexa-3,5-diene-1,2-diol + NAD+
show the reaction diagram
bromobenzene + NADH + H+ + O2
cis-(1S,2S)-3-bromocyclohexa-3,5-diene-1,2-diol + NAD+
show the reaction diagram
-
-
-
0
?
butyl phenyl sulfide + NADH + O2
(R)-butyl phenyl sulfoxide + ?
show the reaction diagram
-
-
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
-
-
-
0
?
cis-1,2-dichloroethene + NADH + O2
?
show the reaction diagram
-
12% of the activity with toluene
-
0
?
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
-
0
?
cis-1-chloro-1-propene + NADH + O2
?
show the reaction diagram
-
5% of the activity with toluene
-
0
?
cis-2-heptene + NADH + O2
heptane-2,3-diol + NAD+
show the reaction diagram
-
-
-
?
cis-2-octene + NADH + O2
octane-2,3-diol + NAD+
show the reaction diagram
-
-
-
?
cis-2-pentene + NADH + O2
pentane-2,3-diol + NAD+
show the reaction diagram
-
16% of the activity with toluene
-
?
cis-dibromoethene + NADH + O2
1,2-dibromoethane-1,2-diol + NAD+
show the reaction diagram
-
13% of the activity with toluene
-
?
cumene + NADH + O2
?
show the reaction diagram
-
-
-
0
?
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
-
-
-
0
?
ethenyl phenyl sulfide + NADH + O2
(R)-ethenyl phenyl sulfoxide + ?
show the reaction diagram
-
-
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+
show the reaction diagram
-
-
-
0
?
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+
show the reaction diagram
-
-
-
0
?
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+
show the reaction diagram
-
-
-
0
?
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+
show the reaction diagram
-
-
-
0
?
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
-
-
-
0
?
ethylbenzene + NADH + O2
ethylbenzene cis-dihydrodiol + NAD+
show the reaction diagram
-
-
-
0
?
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 + H+ + O2
cis-(1S,2R)-indandiol + (1S)-indenol + NAD+
show the reaction diagram
-
-
-
0
?
indene + NADH + O2
cis-(1S, 2R)-indandiol + 1-indenol + 1-indanone + NAD+
show the reaction diagram
-
-
-
0
?
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
-
-
-
0
?
indole + NADH + O2
indigo + NAD+
show the reaction diagram
-
-
-
0
?
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 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+
show the reaction diagram
-
-
-
0
?
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+
show the reaction diagram
-
-
-
0
?
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+
show the reaction diagram
-
-
-
0
?
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+
show the reaction diagram
-
-
-
0
?
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
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+
show the reaction diagram
-
-
-
0
?
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+
show the reaction diagram
-
-
-
0
?
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+
show the reaction diagram
-
-
-
0
?
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+
show the reaction diagram
-
-
-
0
?
p-methoxyphenyl methyl sulfide + O2
p-methoxyphenyl methyl sulfoxide
show the reaction diagram
-
-
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+
show the reaction diagram
-
-
-
0
?
phenylcyclohexane + NADH + O2
(1S,2R)-3-(1-cyclohexyl)-3,5-cyclohexadiene-1,2-diol + ?
show the reaction diagram
-
-
-
?
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+
show the reaction diagram
-
-
-
0
?
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+
show the reaction diagram
-
-
-
0
?
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+
show the reaction diagram
-
-
-
0
?
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+
show the reaction diagram
-
-
-
0
?
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
-
-
-
0
?
propylbenzene + NADH + H+ + O2
cis-(1S,2R)-3-propylcyclohexa-3,5-diene-1,2-diol + cis-(1S,2R)3-[(R)1'-hydroxyethyl]cyclohexa-3,5-diene-1,2-diol + NAD+
show the reaction diagram
-
-
-
0
?
styrene + NADH + H+ + O2
cis-2,3-dihydroxy-1-vinylcyclohexa-4,6-diene + (R)1-phenyl-1,2-ethanediol + NAD+
show the reaction diagram
-
-
-
0
?
thiophene + NADH
?
show the reaction diagram
-
-
-
0
?
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
-
0
?
trans-1-chloro-1-propene + NADH + O2
?
show the reaction diagram
-
4% of the activity with toluene
-
0
?
trans-dibromoethene + NADH + O2
?
show the reaction diagram
-
5% of the activity with toluene
-
0
?
trichloroethene + NADH + H+ + O2
? + NAD+
show the reaction diagram
-
-
-
0
?
trichloroethylene + NADH + O2
?
show the reaction diagram
-
trichloroethylene degradation is mediated by the former degradation of toluene, benzene or cumene
-
0
?
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
-
-
-
0
ir
additional information
?
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