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(+)-(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
-
-
?
1,2-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-dinitrobenzene + NADH + H+ + O2
?
-
-
-
-
?
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-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-indanone + NADH + O2
(S)-2-hydroxy-1-indanone + 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-chloroaniline + NADH + H+ + O2
?
2-chloroaniline + NADH + H+ + O2
? + NAD+
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-chlorothiophene + NADH
?
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-cresol + NADH + H+ + O2
?
-
activity in strain UV4
-
-
?
2-ethylthiophene + NADH
?
2-hexene + NADH + O2
hexane-2,3-diol + NAD+
-
-
-
?
2-indanone + NADH + O2
(S)-2-hydroxy-1-indanone + 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-methoxyphenol + NADH + H+ + O2
(4S,5S)-4,5-dihydroxy-2-methoxycyclohex-2-enone + NAD+
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
-
?
2-methylthiophene + NADH
?
3,4-dichloro-1-butene + NADH + O2
3,4-dichlorobutane-1,2-diol + NAD+
-
23% of the activity with toluene
-
?
3,4-dichloroaniline + NADH + H+ + O2
?
3,4-dichloroaniline + NADH + H+ + O2
? + NAD+
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-chloroaniline + NADH + H+ + O2
?
-
-
-
-
?
3-chloroaniline + NADH + H+ + O2
? + 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
?
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-methoxyphenol + NADH + H+ + O2
(4S,5S)-4,5-dihydroxy-3-methoxycyclohex-2-enone + 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-chloroaniline + NADH + H+ + O2
4-chlorocatechol + 2-amino-5-chlorophenol + NAD+
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
-
-
?
5-cyanoindole + NADH + O2
?
-
-
-
-
?
5-nitroindole + NADH + O2
?
-
-
-
-
?
6-bromoindene + NADH + O2
6-bromoinden-1-ol + NAD+
6-chloroindole + NADH + O2
?
-
-
-
-
?
6-methoxyindole + NADH + O2
?
-
-
-
-
?
7-bromoindole + NADH + O2
?
-
-
-
-
?
7-chloroindole + NADH + O2
?
-
-
-
-
?
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+
-
-
-
-
?
benzaldoxime + NADH + H+ + O2
?
-
-
-
-
?
benzamide iminol + NADH + H+ + O2
?
-
-
-
-
?
benzene + NADH + O2
benzene cis-dihydrodiol + NAD+
-
-
-
-
?
benzene + NADH + O2
benzene dihydrodiol + NAD+
benzyl azide + NADH + H+ + O2
benzonitrile + 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
(1S,2S)-3-bromocyclohexa-3,5-diene-1,2-diol + NAD+
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
?
chlorobenzene + NADH + H+ + O2
(1S,2S)-3-chlorocyclohexa-3,5-diene-1,2-diol + NAD+
chromane + NADH + O2
chromane-4-ol + chromane-4-one + NAD+
cis-1,2-dichloroethene + NADH + H+ + O2
? + NAD+
-
-
-
-
?
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-heptene + NADH + O2
heptane-2,3-diol + NAD+
-
-
-
?
cis-2-octene + NADH + O2
octane-2,3-diol + NAD+
-
-
-
?
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
-
?
cumene + NADH + O2
?
-
-
-
-
?
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+
-
-
-
-
?
ethylbenzene + NADH + O2
?
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
-
?
indane + NADH + O2
(-)-(1R)-indanol + NAD+
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 + NADH + H+ + O2
cis-1,2-dihydoxyindane + 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
?
indole + NADH + H+ + O2
2,2'-bis(2,3-dihydro-3-oxoindolyliden) + NAD+
indole + NADH + O2
?
-
-
-
-
?
indole + NADH + O2
indigo + NAD+
-
-
-
-
?
iodobenzene + NADH + H+ + O2
(1S,2S)-3-iodocyclohexa-3,5-diene-1,2-diol + NAD+
isopropyl phenyl sulfide + NADH + O2
(R)-isopropyl phenyl sulfoxide + ?
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
-
-
-
?
methyl phenyl sulfide + NADH + O2
(R)-methyl phenyl sulfoxide + ?
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+
-
-
-
-
?
propyl phenyl sulfide + NADH + O2
(R)-propyl phenyl sulfoxide + ?
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+
-
-
-
-
?
thiophene + NADH
?
-
-
-
-
?
toluene + NADH + H+ + O2
(1S,2R)-3-methylcyclohexa-3,5-diene-1,2-diol + NAD+
toluene + NADH + O2
(1S,2R)-3-methylcyclohexa-3,5-diene-1,2-diol + 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
-
-
?
trans-dibromoethene + NADH + O2
?
-
5% of the activity with toluene
-
-
?
trichloroethene + NADH + H+ + O2
? + NAD+
-
-
-
-
?
trichloroethylene + NADH + O2
?
-
trichloroethylene degradation is mediated by the former degradation of toluene, benzene or cumene
-
-
?
trichloroethylene + O2 + NADH
?
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
additional information
?
-
(+)-(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
?
-
-
-
-
?
2-chloroaniline + NADH + H+ + O2
?
-
-
-
-
?
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-chlorothiophene + NADH
?
-
-
-
-
?
2-chlorothiophene + NADH
?
-
-
-
-
?
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-ethylthiophene + NADH
?
-
-
-
-
?
2-ethylthiophene + NADH
?
-
-
-
-
?
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+
-
-
-
-
?
2-methylthiophene + NADH
?
-
-
-
-
?
2-methylthiophene + NADH
?
-
-
-
-
?
3,4-dichloroaniline + NADH + H+ + O2
?
-
-
-
-
?
3,4-dichloroaniline + NADH + H+ + O2
?
-
-
-
-
?
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+
-
-
-
-
?
6-bromoindene + NADH + O2
6-bromoinden-1-ol + NAD+
-
-
-
-
?
6-bromoindene + NADH + O2
6-bromoinden-1-ol + NAD+
-
-
-
-
?
benzene + NADH + O2
benzene dihydrodiol + 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+
-
-
-
-
?
chromane + NADH + O2
chromane-4-ol + chromane-4-one + NAD+
-
-
-
-
?
chromane + NADH + O2
chromane-4-ol + chromane-4-one + 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
?
-
-
-
-
?
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+
-
biotransformation with intact cells
+ indan-1-one
?
indane + NADH + O2
(-)-(1R)-indanol + NAD+
-
biotransformation with intact cells
+ indan-1-one
?
indene + NADH + H+ + O2
cis-1,2-dihydoxyindane + NAD+
-
-
-
-
?
indene + NADH + H+ + O2
cis-1,2-dihydoxyindane + NAD+
-
-
-
-
?
indole + NADH + H+ + O2
2,2'-bis(2,3-dihydro-3-oxoindolyliden) + NAD+
-
-
i.e. indigo
-
?
indole + NADH + H+ + O2
2,2'-bis(2,3-dihydro-3-oxoindolyliden) + NAD+
-
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
-
?
iodobenzene + NADH + H+ + O2
(1S,2S)-3-iodocyclohexa-3,5-diene-1,2-diol + NAD+
-
-
-
-
?
iodobenzene + NADH + H+ + O2
(1S,2S)-3-iodocyclohexa-3,5-diene-1,2-diol + NAD+
-
-
-
-
?
isopropyl phenyl sulfide + NADH + O2
(R)-isopropyl phenyl sulfoxide + ?
-
-
more than 98% R-enantiomer
?
isopropyl phenyl sulfide + NADH + O2
(R)-isopropyl phenyl sulfoxide + ?
-
-
more than 98% R-enantiomer
?
methyl phenyl sulfide + NADH + O2
(R)-methyl phenyl sulfoxide + ?
-
-
more than 98% R-enantiomer
?
methyl phenyl sulfide + NADH + O2
(R)-methyl phenyl sulfoxide + ?
-
-
more than 98% R-enantiomer
?
methyl phenyl sulfide + NADH + O2
(R)-methyl phenyl sulfoxide + ?
-
-
more than 98% R-enantiomer
?
propyl phenyl sulfide + NADH + O2
(R)-propyl phenyl sulfoxide + ?
-
-
more than 98% R-enantiomer
?
propyl phenyl sulfide + NADH + O2
(R)-propyl phenyl sulfoxide + ?
-
-
more than 98% R-enantiomer
?
toluene + NADH + H+ + O2
(1S,2R)-3-methylcyclohexa-3,5-diene-1,2-diol + NAD+
-
-
-
-
?
toluene + NADH + H+ + O2
(1S,2R)-3-methylcyclohexa-3,5-diene-1,2-diol + NAD+
-
-
-
?
toluene + NADH + H+ + O2
(1S,2R)-3-methylcyclohexa-3,5-diene-1,2-diol + NAD+
-
-
-
?
toluene + NADH + H+ + O2
(1S,2R)-3-methylcyclohexa-3,5-diene-1,2-diol + NAD+
-
-
-
-
?
toluene + NADH + H+ + O2
(1S,2R)-3-methylcyclohexa-3,5-diene-1,2-diol + NAD+
-
-
-
-
?
toluene + NADH + O2
(1S,2R)-3-methylcyclohexa-3,5-diene-1,2-diol + NAD+
-
-
-
-
?
toluene + NADH + O2
(1S,2R)-3-methylcyclohexa-3,5-diene-1,2-diol + NAD+
-
-
-
?
toluene + NADH + O2
(1S,2R)-3-methylcyclohexa-3,5-diene-1,2-diol + NAD+
-
-
-
-
?
toluene + NADH + O2
(1S,2R)-3-methylcyclohexa-3,5-diene-1,2-diol + NAD+
-
-
-
?
toluene + NADH + O2
(1S,2R)-3-methylcyclohexa-3,5-diene-1,2-diol + NAD+
-
-
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 -
-
?
toluene + NADH + O2
(1S,2R)-3-methylcyclohexa-3,5-diene-1,2-diol + NAD+
-
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
-
-
?
toluene + NADH + O2
(1S,2R)-3-methylcyclohexa-3,5-diene-1,2-diol + NAD+
-
initial enzyme of toluene catabolism
-
-
?
toluene + NADH + O2
(1S,2R)-3-methylcyclohexa-3,5-diene-1,2-diol + NAD+
-
enzyme is involved in meta pathway for catechol degradation
-
-
?
toluene + NADH + O2
(1S,2R)-3-methylcyclohexa-3,5-diene-1,2-diol + NAD+
-
involved in the conversion of aromatic compounds to their corresponding catechols
-
-
?
toluene + NADH + O2
(1S,2R)-3-methylcyclohexa-3,5-diene-1,2-diol + NAD+
-
-
-
-
?
toluene + NADH + O2
(1S,2R)-3-methylcyclohexa-3,5-diene-1,2-diol + NAD+
-
-
-
-
?
toluene + NADH + O2
(1S,2R)-3-methylcyclohexa-3,5-diene-1,2-diol + NAD+
-
-
-
-
?
toluene + NADH + O2
(1S,2R)-3-methylcyclohexa-3,5-diene-1,2-diol + NAD+
-
initial enzyme of toluene catabolism
-
-
?
toluene + NADH + O2
(1S,2R)-3-methylcyclohexa-3,5-diene-1,2-diol + NAD+
-
-
-
-
?
toluene + NADH + O2
(1S,2R)-3-methylcyclohexa-3,5-diene-1,2-diol + NAD+
-
-
-
-
?
trichloroethylene + O2 + NADH
?
-
-
-
-
?
trichloroethylene + O2 + NADH
?
-
25% of the activity with toluene
-
-
?
trifluoromethylbenzene + NADH + H+ + O2
(1S,2R)-3-(trifluoromethyl)cyclohexa-3,5-diene-1,2-diol + NAD+
-
-
-
-
?
trifluoromethylbenzene + NADH + H+ + O2
(1S,2R)-3-(trifluoromethyl)cyclohexa-3,5-diene-1,2-diol + NAD+
-
-
-
-
?
xylene + NADH + O2
?
-
-
-
-
?
xylene + NADH + O2
?
-
involved in the conversion of aromatic compounds to their corresponding catechols
-
-
?
additional information
?
-
-
no reaction with 1-indanone
-
-
?
additional information
?
-
-
the oxygen atom in methyl phenyl sulfoxide is derived exclusively from dioxygen
-
-
?
additional information
?
-
-
the NADH-ferredoxinTOL reductase component catalyzes the NADH-dependent reduction of 2,6-dichloroindophenol, nitroblue tetrazolium and ferricyanide. NADPH is inactive
-
-
?
additional information
?
-
-
activity with alkyl aryl sulfides
-
-
?
additional information
?
-
-
screening of substituted arenes containing remote chiral centers as substrates, enantiomers are indiscriminately processed to diastereomeric pairs
-
-
?
additional information
?
-
-
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
-
-
?
additional information
?
-
-
enzyme catalyzes monooxygenation and dioxygenation of aliphatic olefins
-
-
?
additional information
?
-
-
a high number of 2- or 3-substituted thiophenes were tested as substrates and were found to be metabolized
-
-
?
additional information
?
-
-
catechol and 3-methylcatechol are no substrates
-
-
?
additional information
?
-
-
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
-
-
?
additional information
?
-
-
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
-
-
?
additional information
?
-
-
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
-
-
?
additional information
?
-
-
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
-
-
?
additional information
?
-
-
TodT-P is the active form of the response regulator that induces RNA polymerase to transcribe from the PtodX promoter
-
-
?
additional information
?
-
-
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
-
-
?
additional information
?
-
-
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
-
-
?
additional information
?
-
-
no substrate: 3,5-dichloroaniline
-
-
?
additional information
?
-
-
no activity with 3,5-dichloroaniline
-
-
?
additional information
?
-
-
no reaction with 1-indanone
-
-
?
additional information
?
-
-
no substrate: 3,5-dichloroaniline
-
-
?
additional information
?
-
-
no activity with 3,5-dichloroaniline
-
-
?
additional information
?
-
-
a high number of 2- or 3-substituted thiophenes were tested as substrates and were found to be metabolized
-
-
?
additional information
?
-
-
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
-
-
?
additional information
?
-
-
activity with alkyl aryl sulfides
-
-
?
additional information
?
-
-
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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Subramanian, V.; Liu, T.N.; Yeh, W.K.; Narro, M.; Gibson, D.T.
Purification and properties of NADH-ferredoxinTOL reductase. A component of toluene dioxygenase from Pseudomonas putida
J. Biol. Chem.
256
2723-2730
1981
Pseudomonas putida
brenda
Subramanian, V.; Liu, T.N.; Yeh, W.K.; Gibson, D.T.
Toluene dioxygenase: purification of an iron-sulfur protein by affinity chromatography
Biochem. Biophys. Res. Commun.
91
1131-1139
1979
Pseudomonas putida
brenda
Wackett, L.P.; Kwart, L.D.; Gibson, D.T.
Benzylic monooxygenation catalyzed by toluene dioxygenase from Pseudomonas putida
Biochemistry
27
1360-1367
1988
Pseudomonas putida
brenda
Yeh, W.K.; Gibson, D.T.; Liu, T.N.
Toluene dioxygenase: a multicomponent enzyme system
Biochem. Biophys. Res. Commun.
78
401-410
1977
Pseudomonas putida
brenda
Zylstra, G.J.; Gibson, D.T.
Toluene degradation by Pseudomonas putida F1. Nucleotide sequence of the todC1C2BADE genes and their expression in Escherichia coli
J. Biol. Chem.
264
14940-14946
1989
Pseudomonas putida
brenda
Stephens, G.M.; Sidebotham, J.M.; Mann, N.H.; Dalton, H.
Cloning and expression in Escherichia coli of the toluene dioxygenase gene from Pseudomonas putida
FEMS Microbiol. Lett.
57
295-300
1989
Pseudomonas putida, Pseudomonas putida NCIB11767
brenda
Zylstra, G.J.; Wackett, L.P.; Gibson, D.T.
Trichloroethylene degradation by Escherichia coli containing the cloned Pseudomonas putida F1 toluene dioxygenase genes
Appl. Environ. Microbiol.
55
3162-3166
1989
Pseudomonas putida
brenda
Subramanian, V.; Liu, T.N.; Yeh, W.K.; Serdar, C.M.; Wackett, L.P.; Gibson, D.T.
Purification and properties of ferredoxinTOL. A component of toluene dioxygenase from Pseudomonas putida F1
J. Biol. Chem.
260
2355-2363
1985
Pseudomonas putida
brenda
Zylstra, G.J.; McCombie, W.R.; Gibson, D.T.; Finette, B.A.
Toluene degradation by Pseudomonas putida F1: genetic organization of the tod operon
Appl. Environ. Microbiol.
54
1498-1503
1988
Pseudomonas putida
brenda
Wackett, L.P.
Toluene dioxygenase from Pseudomonas putida F1
Methods Enzymol.
188
39-45
1990
Pseudomonas putida
brenda
Lange, C.C.; Wackett, L.P.
Oxidation of aliphatic olefins by toluene dioxygenase: enzyme rates and product identification
J. Bacteriol.
179
3858-3865
1997
Pseudomonas putida
brenda
Jiang, H.; Parales, R.E.; Gibson, D.T.
The alpha subunit of toluene dioxygenase from Pseudomonas putida F1 can accept electrons from reduced FerredoxinTOL but is catalytically inactive in the absence of the beta subunit
Appl. Environ. Microbiol.
65
315-318
1999
Pseudomonas putida
brenda
Lynch, N.A.; Jiang, H.; Gibson, D.T.
Rapid purification of the oxygenase component of toluene dioxygenase from a polyol-responsive monoclonal antibody
Appl. Environ. Microbiol.
62
2133-2137
1996
Pseudomonas putida
brenda
Jiang, H.; Parales, R.E.; Lynch, N.A.; Gibson, D.T.
Site-directed mutagenesis of conserved amino acids in the alpha subunit of toluene dioxygenase: potential mononuclear non-heme iron coordination sites
J. Bacteriol.
178
3133-3139
1996
Pseudomonas putida
brenda
Leahy, J.G.; Olsen, R.H.
Kinetics of toluene degradation by toluene-oxidizing bacteria as a function of oxygen concentration, and the effect of nitrate
FEMS Microbiol. Ecol.
23
23-30
1997
Pseudomonas sp., Pseudomonas putida, Pseudomonas fluorescens, Pseudomonas sp. W31, Pseudomonas fluorescens CFS215
brenda
Lee, K.; Brand, J.M.; Gibson, D.T.
Stereospecific sulfoxidation by toluene and naphthalene dioxygenases
Biochem. Biophys. Res. Commun.
212
9-15
1995
Pseudomonas putida
brenda
Li, S.; Wackett, L.P.
Trichloroethylene oxidation by toluene dioxygenase
Biochem. Biophys. Res. Commun.
185
443-451
1992
Pseudomonas putida
brenda
Resnick, S.M.; Torok, D.S.; Lee, K.; Brand, J.M.; Gibson, D.T.
Regiospecific and stereoselective hydroxylation of 1-indanone and 2-indanone by naphthalene dioxygenase and toluene dioxygenase
Appl. Environ. Microbiol.
60
3323-3328
1994
Pseudomonas putida, Pseudomonas putida F39D
brenda
Bui, V.P.; Vidar Hansen, T.; Stenstrom, Y.; Hudlicky, T.; Ribbons, D.W.
A study of substrate specificity of toluene dioxygenase in processing aromatic compounds containing benzylic and/or remote chiral centers
New J. Chem.
25
116-124
2001
Pseudomonas putida
-
brenda
Boyd, D.R.; Sharma, N.D.; Haughey, S.A.; Kennedy, M.A.; McMurray, B.T.; Sheldrake, G.N.; Allen, C.C.R.; Dalton, H.; Sproule, K.
Toluene and naphthalene dioxygenase-catalyzed sulfoxidation of alkyl aryl sulfides
J. Chem. Soc. Perkin Trans.
1
1929-1934
1998
Pseudomonas putida, Pseudomonas putida UV4
-
brenda
Bowers, N.I.; Boyd, D.R.; Sharma, N.D.; Goodrich, P.A.; Groocock, M.R.; Blacker, A.J.; Goode, P.; Dalton, H.
Stereoselective benzylic hydroxylation of 2-substituted indanes using toluene dioxygenase as biocatalyst
J. Chem. Soc. Perkin Trans.
1
1453-1462
1999
Pseudomonas putida, Pseudomonas putida UV4
-
brenda
Sakamoto, T.; Joern, J.M.; Arisawa, A.; Arnold, F.H.
Laboratory evolution of toluene dioxygenase to accept 4-picoline as a substrate
Appl. Environ. Microbiol.
67
3882-3887
2001
Pseudomonas putida
brenda
Bagneris, C.; Cammack, R.; Mason, J.R.
Subtle difference between benzene and toluene dioxygenases of Pseudomonas putida
Appl. Environ. Microbiol.
71
1570-1580
2005
Pseudomonas putida
brenda
Xu, Z.; Mulchandani, A.; Chen, W.
Detection of benzene, toluene, ethyl benzene, and xylenes (BTEX) using toluene dioxygenase-peroxidase coupling reactions
Biotechnol. Prog.
19
1812-1815
2003
Pseudomonas putida
brenda
Ni, Y.; Chen, R.R.
Lipoprotein mutation accelerates substrate permeability-limited toluene dioxygenase-catalyzed reaction
Biotechnol. Prog.
21
799-805
2005
Pseudomonas putida
brenda
Kim, J.Y.; Lee, K.; Kim, Y.; Kim, C.K.; Lee, K.
Production of dyestuffs from indole derivatives by naphthalene dioxygenase and toluene dioxygenase
Lett. Appl. Microbiol.
36
343-348
2003
Pseudomonas putida
brenda
Boyd, D.R.; Sharma, N.D.; Bowers, N.I.; Boyle, R.; Harrison, J.S.; Lee, K.; Bugg, T.D.; Gibson, D.T.
Stereochemical and mechanistic aspects of dioxygenase-catalysed benzylic hydroxylation of indene and chromane substrates
Org. Biomol. Chem.
1
1298-1307
2003
Pseudomonas putida, Pseudomonas putida UV4
brenda
Boyd, D.R.; Sharma, N.D.; Gunaratne, N.; Haughey, S.A.; Kennedy, M.A.; Malone, J.F.; Allen, C.C.; Dalton, H.
Dioxygenase-catalysed oxidation of monosubstituted thiophenes: sulfoxidation versus dihydrodiol formation
Org. Biomol. Chem.
1
984-994
2003
Pseudomonas putida, Pseudomonas putida UV4
brenda
Lee, K.; Friemann, R.; Parales, J.V.; Gibson, D.T.; Ramaswamy, S.
Purification, crystallization and preliminary X-ray diffraction studies of the three components of the toluene 2,3-dioxygenase enzyme system
Acta crystallogr. Sect. F
61
669-672
2005
Pseudomonas putida
brenda
Boyd, D.R.; Sharma, N.D.; Bowers, N.I.; Dalton, H.; Garrett, M.D.; Harrison, J.S.; Sheldrake, G.N.
Dioxygenase-catalysed oxidation of disubstituted benzene substrates: benzylic monohydroxylation versus aryl cis-dihydroxylation and the meta effect
Org. Biomol. Chem.
4
3343-3349
2006
Pseudomonas putida, Pseudomonas putida UV4
brenda
Boyd, D.R.; Sharma, N.D.; Llamas, N.M.; Coen, G.P.; McGeehin, P.K.; Allen, C.C.
Chemoenzymatic synthesis of trans-dihydrodiol derivatives of monosubstituted benzenes from the corresponding cis-dihydrodiol isomers
Org. Biomol. Chem.
5
514-522
2007
Pseudomonas putida, Pseudomonas putida UV4
brenda
Finn, K.J.; Collins, J.; Hudlicky, T.
Toluene dioxygenase-mediated oxidation of dibromobenzenes. Absolute stereochemistry of new metabolites and synthesis of (-)-conduritol E
Tetrahedron
62
7471-7476
2006
Escherichia coli, Escherichia coli JM 109 (pDTG601)
-
brenda
Finn, K.J.; Rochon, L.; Hudlicky, T.
Processing of cyclopropylarenes by toluene dioxygenase: isolation and absolute configuration of metabolites
Tetrahedron Asymmetry
16
3606-3613
2005
Escherichia coli, Escherichia coli JM 109 (pDTG601)
-
brenda
Ramos-Gonzalez, M.I.; Ben-Bassat, A.; Campos, M.J.; Ramos, J.L.
Genetic engineering of a highly solvent-tolerant Pseudomonas putida strain for biotransformation of toluene to p-hydroxybenzoate
Appl. Environ. Microbiol.
69
5120-5127
2003
Pseudomonas putida, Pseudomonas putida DOT-T1E
brenda
Morono, Y.; Unno, H.; Tanji, Y.; Hori, K.
Addition of aromatic substrates restores trichloroethylene degradation activity in Pseudomonas putida F1
Appl. Environ. Microbiol.
70
2830-2835
2004
Pseudomonas putida
brenda
Shingleton, J.T.; Applegate, B.A.; Baker, A.J.; Sayler, G.S.; Bienkowski, P.R.
Quantification of toluene dioxygenase induction and kinetic modeling of TCE cometabolism by Pseudomonas putida TVA8
Biotechnol. Bioeng.
76
341-350
2001
Pseudomonas putida, Pseudomonas putida TVA8
brenda
Lovanh, N.; Alvarez, P.J.
Effect of ethanol, acetate, and phenol on toluene degradation activity and tod-lux expression in Pseudomonas putida TOD102: evaluation of the metabolic flux dilution model
Biotechnol. Bioeng.
86
801-808
2004
Pseudomonas putida
brenda
Woo, H.; Sanseverino, J.; Cox, C.D.; Robinson, K.G.; Sayler, G.S.
The measurement of toluene dioxygenase activity in biofilm culture of Pseudomonas putida F1
J. Microbiol. Methods
40
181-191
2000
Pseudomonas putida
brenda
Zhang, N.; Stewart, B.G.; Moore, J.C.; Greasham, R.L.; Robinson, D.K.; Buckland, B.C.; Lee, C.
Directed evolution of toluene dioxygenase from Pseudomonas putida for improved selectivity toward cis-indandiol during indene bioconversion
Metab. Eng.
2
339-348
2000
Pseudomonas putida
brenda
Boyd, D.R.; Sharma, N.D.; Coen, G.P.; Gray, P.J.; Malone, J.F.; Gawronski, J.
Enzyme-catalysed synthesis and absolute configuration assignments of cis-dihydrodiol metabolites from 1,4-disubstituted benzenes
Chemistry
13
5804-5811
2007
Pseudomonas putida, Pseudomonas putida UV4
brenda
Ouyang, S.P.; Liu, Q.; Sun, S.Y.; Chen, J.C.; Chen, G.Q.
Genetic engineering of Pseudomonas putida KT2442 for biotransformation of aromatic compounds to chiral cis-diols
J. Biotechnol.
132
246-250
2007
Pseudomonas putida, Pseudomonas putida KT 2442
brenda
Friemann, R.; Lee, K.; Brown, E.N.; Gibson, D.T.; Eklund, H.; Ramaswamy, S.
Structures of the multicomponent Rieske non-heme iron toluene 2,3-dioxygenase enzyme system
Acta Crystallogr. Sect. D
65
24-33
2009
Pseudomonas putida
brenda
da Silva, M.; Alvarez, P.
Indole-based assay to assess the effect of ethanol on Pseudomonas putida F1 dioxygenase activity
Biodegradation
2009
1-6
2009
Pseudomonas putida F1
-
brenda
Boyd, D.R.; Sharma, N.D.; Malone, J.F.; Allen, C.C.
New families of enantiopure cyclohexenone cis-diol, o-quinol dimer and hydrate metabolites from dioxygenase-catalysed dihydroxylation of phenols
Chem. Commun. (Camb. )
2009
3633-3635
2009
Pseudomonas putida
brenda
Kwit, M.; Gawronski, J.; Boyd, D.R.; Sharma, N.D.; Kaik, M.; More O'Ferrall, R.A.; Kudavalli, J.S.
Toluene dioxygenase-catalyzed synthesis of cis-dihydrodiol metabolites from 2-substituted naphthalene substrates: assignments of absolute configurations and conformations from circular dichroism and optical rotation measurements
Chemistry
14
11500-11511
2008
Pseudomonas putida, Pseudomonas putida UV4
brenda
Hamada, T.; Maeda, Y.; Matsuda, H.; Sameshima, Y.; Honda, K.; Omasa, T.; Kato, J.; Ohtake, H.
Effect of cell-surface hydrophobicity on bacterial conversion of water-immiscible chemicals in two-liquid-phase culture systems
J. Biosci. Bioeng.
108
116-120
2009
Pseudomonas putida
brenda
Lacal, J.; Guazzaroni, M.E.; Busch, A.; Krell, T.; Ramos, J.L.
Hierarchical binding of the TodT response regulator to its multiple recognition sites at the tod pathway operon promoter
J. Mol. Biol.
376
325-337
2008
Pseudomonas putida
brenda
Busch, A.; Lacal, J.; Silva-Jimenez, H.; Krell, T.; Ramos, J.L.
Catabolite repression of the TodS/TodT two-component system and effector-dependent transphosphorylation of TodT as the basis for toluene dioxygenase catabolic pathway control
J. Bacteriol.
192
4246-4250
2010
Pseudomonas putida
brenda
Boyd, D.R.; Sharma, N.D.; Stevenson, P.J.; Blain, M.; McRoberts, C.; Hamilton, J.T.; Argudo, J.M.; Mundi, H.; Kulakov, L.A.; Allen, C.C.
Dioxygenase-catalysed cis-dihydroxylation of meta-substituted phenols to yield cyclohexenone cis-diol and derived enantiopure cis-triol metabolites
Org. Biomol. Chem.
9
1479-1490
2011
Pseudomonas putida, Pseudomonas putida UV4
brenda
Clingenpeel, S.; Moan, J.; McGrath, D.; Hungate, B.; Watwood, M.
Stable carbon isotope fractionation in chlorinated ethene degradation by bacteria expressing three toluene oxygenases
Front. Microbiol.
3
63
2012
Pseudomonas putida
brenda
Lin, T.Y.; Werther, T.; Jeoung, J.H.; Dobbek, H.
Suppression of electron transfer to dioxygen by charge transfer and electron transfer complexes in the FAD-dependent reductase component of toluene dioxygenase
J. Biol. Chem.
287
38338-38346
2012
Pseudomonas putida
brenda
Nitisakulkan, T.; Oku, S.; Kudo, D.; Nakashimada, Y.; Tajima, T.; Vangnai, A.; Kato, J.
Degradation of chloroanilines by toluene dioxygenase from Pseudomonas putida T57
J. Biosci. Bioeng.
117
292-297
2013
Pseudomonas putida, Pseudomonas putida T57
brenda
Vila, M.; Umpierrez, D.; Veiga, N.; Seoane, G.; Carrera, I.; Rodriguez Giordano, S.
Site-directed mutagenesis studies on the toluene dioxygenase enzymatic system Role of phenylalanine 366, threonine 365 and isoleucine 324 in the chemo-, regio-, and stereoselectivity
Adv. Synth. Catal.
359
2149-2157
2017
Pseudomonas putida
-
brenda
Vila, M.A.; Pazos, M.; Iglesias, C.; Veiga, N.; Seoane, G.; Carrera, I.
Toluene dioxygenase-catalysed oxidation of benzyl azide to benzonitrile mechanistic insights for an unprecedented enzymatic transformation
ChemBioChem
17
291-295
2016
Pseudomonas putida
brenda
Nitisakulkan, T.; Oku, S.; Kudo, D.; Nakashimada, Y.; Tajima, T.; Vangnai, A.; Kato, J.
Degradation of chloroanilines by toluene dioxygenase from Pseudomonas putida T57
J. Biosci. Bioeng.
117
292-297
2014
Pseudomonas putida, Pseudomonas putida T57
brenda
Vila, M.; Umpierrez, D.; Seoane, G.; Rodriguez, S.; Carrera, I.; Veiga, N.
Computational insights into the oxidation of mono- and 1,4 disubstituted arenes by the toluene dioxygenase enzymatic complex
J. Mol. Catal. B
133
5410-5419
2016
Pseudomonas putida (A5W4F2), Pseudomonas putida strain ATCC 700007 (A5W4F2)
-
brenda
Hoering, P.; Rothschild-Mancinelli, K.; Sharma, N.; Boyd, D.; Allen, C.
Oxidative biotransformations of phenol substrates catalysed by toluene dioxygenase A molecular docking study
J. Mol. Catal. B
134
396-406
2016
Pseudomonas putida, Pseudomonas putida UV4
-
brenda
Boyd, D.R.; Sharma, N.D.; Malone, J.F.; McIntyre, P.B.; McRoberts, C.; Floyd, S.; Allen, C.C.; Gohil, A.; Coles, S.J.; Horton, P.N.; Stevenson, P.J.
Toluene dioxygenase-catalyzed synthesis and reactions of cis-diol metabolites derived from 2- and 3-methoxyphenols
J. Org. Chem.
80
3429-3439
2015
Pseudomonas putida, Pseudomonas putida UV4
brenda
Froese, J.; Endoma-Arias, M.; Hudlicky, T.
Processing of o-halobenzoates by toluene dioxygenase. The role of the alkoxy functionality in the regioselectivity of the enzymatic dihydroxylation reaction
Org. Process Res. Dev.
18
801-809
2014
Pseudomonas putida
-
brenda
Wissner, J.L.; Ludwig, J.; Escobedo-Hinojosa, W.; Hauer, B.
An enhanced toluene dioxygenase platform for the production of cis-1,2-dihydrocatechol in Escherichia coli BW25113 lacking glycerol dehydrogenase activity
J. Biotechnol.
325
380-388
2021
Pseudomonas putida (A5W4F2 AND A5W4F1), Pseudomonas putida
brenda