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Information on EC 1.14.12.11 - toluene dioxygenase
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1.14.12.11 toluene dioxygenaseIUBMB Comments
A system, containing a reductase which is an iron-sulfur flavoprotein (FAD), an iron-sulfur oxygenase, and a ferredoxin. Some other aromatic compounds, including ethylbenzene, 4-xylene and some halogenated toluenes, are converted into the corresponding cis-dihydrodiols.
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Word Map
- 1.14.12.11
- putida
- naphthalene
- trichloroethylene
- ethylbenzene
- chlorobenzene
- cis-dihydrodiols
- dihydrodiols
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cis-dihydroxylation
- dot-t1e
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ring-hydroxylating
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cis-toluene
- indene
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cis-diols
- pseudoalcaligenes
- 1-indanone
-
toluene-grown
- 3-methylcatechol
- synthesis
- analysis
- degradation
The enzyme appears in viruses and cellular organisms
Reaction Schemes
Synonyms
toluene dioxygenase, todc1c2ba, toluene 2,3-dioxygenase, isptol, oxygenasetol, 
more
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
ISPTOL
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oxygenase component of the toluene dioxygenase multienzyme system
oxygenase, toluene 2,3-di-
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TDO
Tod
todC1C2BA
additional information
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part of a multiple enzyme complex: reductase, ferredoxin, dioxygenase
TDO
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TDO
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
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+
reaction mechanism, structure-function reklationship of the enzyme organized in a multicomponent Rieske non-heme iron toluene 2,3-dioxygenase enzyme system, overview
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toluene + NADH + H+ + O2 = (1S,2R)-3-methylcyclohexa-3,5-diene-1,2-diol + NAD+
formation of a stable charge transfer complex between the reduced reductase and NAD+ at the end of the reductive half-reaction, which is substantially less reactive toward dioxygen than the reduced reductase in the absence of NAD+. The nicotinamide ring and the protein matrix shield the reactive C4a position of the isoalloxazine ring and force the tricycle into an atypical planar conformation, both factors disfavoring the reaction of the reduced flavin with dioxygen. A rapid electron transfer from the charge transfer complex to electron acceptors further reduces the risk of unwanted side reactions, there is a short distance between the electron-donating and -accepting cofactors. Attraction between the two proteins is likely mediated by opposite charges at one large patch of the complex interface
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
oxidation
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redox reaction
reduction
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redox reaction
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redox reaction
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the toluene 2,3-dioxygenase consists of three components: a reductase transfers electrons from NADH to a Rieske [2Fe-2S] ferredoxin which shuttles electrons to a dioxygenase which catalyzes the formation of (1S,2R)-3-methylcyclohexa-3,5-diene-1,2-diol
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PATHWAY SOURCE
PATHWAYS
BRENDA
KEGG
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SYSTEMATIC NAME
IUBMB Comments
toluene,NADH:oxygen oxidoreductase (1,2-hydroxylating)
A system, containing a reductase which is an iron-sulfur flavoprotein (FAD), an iron-sulfur oxygenase, and a ferredoxin. Some other aromatic compounds, including ethylbenzene, 4-xylene and some halogenated toluenes, are converted into the corresponding cis-dihydrodiols.
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CAS REGISTRY NUMBER
COMMENTARY
120038-36-0
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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+
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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
?
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4% of the activity with toluene
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?
1,1'-(1S,2S)-cyclopropane-1,2-diyldibenzene + NADH + H+ + O2
(1S,2R)-3-[(1S,2S)-2-phenylcyclopropyl]cyclohexa-3,5-diene-1,2-diol + (1S,2R)-3-[(1R,2R)-2-phenylcyclopropyl]cyclohexa-3,5-diene-1,2-diol + NAD+
1,1-dichloro-1-propene + NADH + O2
3,3-dichloro-2-propene-1-ol + NAD+
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6% of the activity with toluene
-
?
1,1-dichloro-1-propene + NADH + O2
?
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18% of the activity with toluene
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-
?
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+
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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+
-
-
-
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?
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+
-
-
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?
1-chloro-4-propylbenzene + NADH + H+ + O2
(1R,2R)-3-chloro-6-propylcyclohexa-3,5-diene-1,2-diol + NAD+
-
-
-
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?
1-ethyl-2-fluorobenzene + NADH + H+ + O2
(1S,2R)-3-ethyl-4-fluorocyclohexa-3,5-diene-1,2-diol + NAD+
-
-
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?
1-ethyl-2-iodobenzene + NADH + H+ + O2
(1S,2R)-3-ethyl-4-iodocyclohexa-3,5-diene-1,2-diol + NAD+
-
-
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?
1-ethyl-3-fluorobenzene + NADH + H+ + O2
(1S,2R)-3-ethyl-5-fluorocyclohexa-3,5-diene-1,2-diol + NAD+
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?
1-ethyl-4-fluorobenzene + NADH + H+ + O2
(1R,2R)-3-ethyl-6-fluorocyclohexa-3,5-diene-1,2-diol + NAD+
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?
1-ethyl-4-iodobenzene + NADH + H+ + O2
(1R,2R)-3-ethyl-6-iodocyclohexa-3,5-diene-1,2-diol + NAD+
-
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-
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?
1-fluoro-2-propylbenzene + NADH + H+ + O2
(1S,2R)-4-fluoro-3-propylcyclohexa-3,5-diene-1,2-diol + NAD+
-
-
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?
1-fluoro-4-propylbenzene + NADH + H+ + O2
(1R,2R)-3-fluoro-6-propylcyclohexa-3,5-diene-1,2-diol + NAD+
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?
1-phenylcyclohexene + NADH + O2
(1S,2R)-3-(1-cyclohexenyl)-3,5-cyclohexadiene-1,2-diol + ?
-
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?
2,3-dichloro-1-propene + NADH + O2
2,3-dichloro-2-propene-1-ol + NAD+
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19% of the activity with toluene
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?
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+
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biotransformation with intact cells
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?
2-bromoindane + O2 + NADH
(-)-cis-(1S,2R)-2-bromoindan-1-ol + (+)-trans-(1S,3S)-1,3-dihydroxy-2-bromoindane + NAD+
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biotransformation with intact cells
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?
2-carbamoylindane + O2 + NADH
(-)-cis-(1S,2R)-2-azoindan-1-ol + NAD+
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biotransformation with intact cells
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?
2-chloroindane + O2 + NADH
(-)-cis-(1S,2R)-2-chloroindan-1-ol + (+)-trans-(1R,2R)-2-chloroindan-1-ol + NAD+
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biotransformation with intact cells
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?
2-chloroindane + O2 + NADH
(-)-trans-(1S,3S)-1,3-dihydroxy-2-chloroindane + NAD+
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biotransformation with intact cells
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?
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+
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biotransformation with intact cells
-
-
?
2-methoxyindane + O2 + NADH
(-)-cis-(1S,2R)-2-methoxyindan-1-ol + (-)-trans-(1R,2R)-2-methoxyindan-1-ol + NAD+
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biotransformation with intact cells
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?
2-methylindan + O2 + NADH
(-)-trans-(1R,3R)-1,3-dihydroxy-2-methylindane + (-)-cis-(2S,3R)-3-hydroxy-2-methylindan-1-one + (-)-cis-(1R,2R)-1-hydroxy-2-methylindane + (-)-(2R)-2-methyindan-1-one + NAD+
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biotransformation with intact cells
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?
3,4-dichloro-1-butene + NADH + O2
3,4-dichlorobutane-1,2-diol + NAD+
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23% of the activity with toluene
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?
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+
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alkyl-substituted cyclohexenone cis-diols are formed as the most significant metabolites prior to extraction
-
?
3-phenylcyclohexene + NADH + O2
(1S,2R)-3-(cyclohexenyl)-3,5-cyclohexadiene-1,2-diol + ?
-
-
-
?
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 + ?
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E. coli expressed mutant enzyme TDO 2-B38, in which the wild-type stop codon is replaced with a codon encoding threonine, exhibits 5.6-times higher activity towards 4-picoline than the wild-type enzyme
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?
4-xylene + NADH + H+ + O2
4-xylenol + NAD+ + H2O
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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 + ?
-
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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-chlorothiophene + NADH
?