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Information on EC 1.14.13.22 - cyclohexanone monooxygenase
for references in articles please use BRENDA:EC1.14.13.22
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EC Tree 1 Oxidoreductases
1.14 Acting on paired donors, with incorporation or reduction of molecular oxygen
1.14.13 With NADH or NADPH as one donor, and incorporation of one atom of oxygen into the other donor
1.14.13.22 cyclohexanone monooxygenase
IUBMB Comments
A flavoprotein (FAD). In the catalytic mechanism of this enzyme, the nucleophilic species that attacks the carbonyl group is a peroxyflavin intermediate that is generated by reaction of the enzyme-bound flavin cofactor with NAD(P)H and oxygen . This enzyme is able to catalyse a wide range of oxidative reactions, including enantioselective Baeyer-Villiger reactions , sulfoxidations , amine oxidations and epoxidations .
The expected taxonomic range for this enzyme is: Bacteria, Eukaryota
- 1.14.13.22
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baeyer-villiger
- acinetobacter
- lactones
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bvmos
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ncimb
- calcoaceticus
- cyclohexanol
- synthesis
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criegee
- epsilon-caprolactone
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c4a-peroxyflavin
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biooxidation
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bicyclo3.2.0hept-2-en-6-one
- phenylacetone
- cyclopentanone
- biotechnology
showSynonyms
cyclohexanone monooxygenase, cyclohexanone oxygenase, more
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
CAMO
CHMO
ChnB
chnB protein
CMO
cycloalkaone monooxygenase
cyclohexanone 1, 2-mono-oxygenase
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cyclohexanone mono-oxygenase
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cyclohexanone monooxygenase
cyclohexanone oxygenase
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cyclohexanone:NADPH:oxygen oxidoreductase (lactone-forming)
oxygenase, cyclohexanone mono-
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CHMO
2 cyclohexanone monooxygenase related genes chnB1 and chnB2
cyclohexanone:NADPH:oxygen oxidoreductase (lactone-forming)
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cyclohexanone:NADPH:oxygen oxidoreductase (lactone-forming)
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
cyclohexanone + NADPH + H+ + O2 = hexano-6-lactone + NADP+ + H2O
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cyclohexanone + NADPH + H+ + O2 = hexano-6-lactone + NADP+ + H2O
stereochemistry
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cyclohexanone + NADPH + H+ + O2 = hexano-6-lactone + NADP+ + H2O
reaction mechanism
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cyclohexanone + NADPH + H+ + O2 = hexano-6-lactone + NADP+ + H2O
mechanistic study
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cyclohexanone + NADPH + H+ + O2 = hexano-6-lactone + NADP+ + H2O
mechanistic study
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cyclohexanone + NADPH + H+ + O2 = hexano-6-lactone + NADP+ + H2O
mechanistic study
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cyclohexanone + NADPH + H+ + O2 = hexano-6-lactone + NADP+ + H2O
re-side specificity of cofactor binding, stereochemistry
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cyclohexanone + NADPH + H+ + O2 = hexano-6-lactone + NADP+ + H2O
kinetic studies
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cyclohexanone + NADPH + H+ + O2 = hexano-6-lactone + NADP+ + H2O
ter-ter mechanism
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cyclohexanone + NADPH + H+ + O2 = hexano-6-lactone + NADP+ + H2O
a stable 4a-hydroperoxy-flavin carries out a nucleophilic attack on the ketone
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cyclohexanone + NADPH + H+ + O2 = hexano-6-lactone + NADP+ + H2O
general mechanistic scheme
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cyclohexanone + NADPH + H+ + O2 = hexano-6-lactone + NADP+ + H2O
stereochemistry and enantioselectivity of the oxidation reaction depends strongly on the structure and stereochemistry of the substrates
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cyclohexanone + NADPH + H+ + O2 = hexano-6-lactone + NADP+ + H2O
enantioselectivity
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cyclohexanone + NADPH + H+ + O2 = hexano-6-lactone + NADP+ + H2O
enantioselectivity
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cyclohexanone + NADPH + H+ + O2 = hexano-6-lactone + NADP+ + H2O
regioselectivity
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cyclohexanone + NADPH + H+ + O2 = hexano-6-lactone + NADP+ + H2O
mechanistic study
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
oxidation
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oxygen ring insertion reaction
redox reaction
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reduction
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PATHWAY SOURCE
PATHWAYS
BRENDA
MetaCyc
cyclohexanol degradation
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SYSTEMATIC NAME
IUBMB Comments
cyclohexanone,NADPH:oxygen oxidoreductase (lactone-forming)
A flavoprotein (FAD). In the catalytic mechanism of this enzyme, the nucleophilic species that attacks the carbonyl group is a peroxyflavin intermediate that is generated by reaction of the enzyme-bound flavin cofactor with NAD(P)H and oxygen [2]. This enzyme is able to catalyse a wide range of oxidative reactions, including enantioselective Baeyer-Villiger reactions [3], sulfoxidations [4], amine oxidations [5] and epoxidations [6].
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CAS REGISTRY NUMBER
COMMENTARY
52037-90-8
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59088-27-6
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
LITERATURE
COMMENTARY
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
(1aS,4aS,8aS)-8a-methylhexahydronaphthalene-1,6-dione + NADPH + O2
(5aR,9aS)-9a-methylhexahydrobenzo[b]oxepine-2,7-dione + NADP+ + H2O
(1R)-bicyclo[2.2.1]heptane-2,5-dione + NADPH + O2
? + NADP+ + H2O
Substrates: 74.4% of the activity with cyclohexanone
Products: -
Products: -
?
(2R)-2-ethylcyclohexanone + NADPH + H+ + O2
(7S)-7-ethyloxepan-2-one + NADP+ + H2O
Substrates: 92% conversion, 30% enantiomeric excess, (-)-product
Products: -
Products: -
?
(2R,6S)-2,6-dimethylcyclohexanone + NADPH + H+ + O2
cis-3, 7-dimethyl-2-oxepanone + NADP+ + H2O
Substrates: -
Products: -
Products: -
?
(2R,6S)-2,6-dimethylcyclohexanone + NADPH + O2 + H+
(3R,7S)-3,7-dimethyloxepan-2-one + NADP+ + H2O
(2S)-2-(prop-2-en-1-yl)cyclohexanone + NADPH + H+ + O2
(7R)-7-(prop-2-en-1-yl)oxepan-2-one + NADP+ + H2O
Substrates: 75% conversion, 99% enantiomeric excess, (-)-product
Products: -
Products: -
?
(3R)-3-(1-methylethenyl)cyclohexanone + NADPH + O2 + H+
(6S)-6-(1-methylethenyl)oxepan-2-one + NADP+ + H2O
(4aR,8aS)-8a-methylhexahydronaphthalene-1,6(2H,5H)-dione + NADPH + O2
(5aR,9aS)-9a-methylhexahydrobenzo[b]oxepine-2,7-dione + (4aS,6S,8aR)-6-hydroxy-8a-methyloctahydronaphthalen-1-one + NADP+ + H2O
(S)-dithiane sulfoxide + NADPH + O2
?
-
Substrates: recombinant enzyme in E. coli or Saccharomyces cerevisiae
Products: -
Products: -
?
1,4-dioxaspiro[4.5]decan-8-one + NADPH + H+ + O2
1,4,8-trioxa-spiro[4,6]undecan-9-one + NADP+ + H2O
Substrates: -
Products: -
Products: -
?
1,4-dioxaspiro[4.5]decan-8-one + NADPH + O2 + H+
1,4,8-trioxaspiro[4.6]undecan-9-one + NADP+ + H2O
1-oxa-2-oxocycloheptane + NADPH + O2
?
-
Substrates: oxidation
Products: -
Products: -
?
2 thioanisole + NADPH + H+ + O2
(R)-thioanisole sulfoxide + (S)-thioanisole sulfoxide + 2 NADP+ + 2 H2O
2,2,6-trimethylcyclohexanone + NADPH + H+ + O2
3,7,7-trimethyloxepan-2-one + NADP+ + H2O
Substrates: -
Products: -
Products: -
?
2-(methylsulfanyl)naphthalene + NADPH + H+ + O2
2-(methanesulfinyl)naphthalene + NADP+ + H2O
2-hexyl-cyclopentanone + NADPH + O2
?
-
Substrates: -
Products: -
Products: -
?
2-hexylcyclopentanone + NADPH + H+ + O2
6-hexyl-tetrahydro-pyran-2-one + NADP+ + H2O
Substrates: -
Products: -
Products: -
?
2-hexylcyclopentanone + NADPH + O2 + H+
6-hexyltetrahydro-2H-pyran-2-one + NADP+ + H2O
-
Substrates: -
Products: 82% conversion at 20 h
Products: 82% conversion at 20 h
?
2-hydroxycyclobutanone + NADPH + H+ + O2
1-oxa-2-oxo-3-hydroxycyclopentane + NADP+ + H2O
Substrates: 67.3% of the activity with cyclohexanone
Products: -
Products: -
?
2-hydroxyethyl methyl sulfide + NADPH + O2
2-hydroxyethyl methyl sulfoxide + NADP+ + H2O
-
Substrates: -
Products: -
Products: -
?
2-methylcyclohexanone + NADPH + O2 + H+
7-methyloxepan-2-one + NADP+ + H2O
-
Substrates: -
Products: -
Products: -
?
2-methylcyclohexyl boronic acid + NADPH + O2
2-methylcyclohexanol + BO3- + NADP+ + H2O
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Substrates: racemic substrate
Products: -
Products: -
?
2-phenylcyclohexanone + NADPH + H+ + O2
3-phenyloxepan-2-one + NADP+ + H2O
Substrates: -
Products: -
Products: -
?
2-phenylcyclohexanone + NADPH + O2
1-oxa-2-oxo-3-phenylcycloheptane + NADP+ + H2O
-
Substrates: slight
Products: -
Products: -
?
2-phenylcyclohexanone + NADPH + O2 + H+
7-phenyloxepan-2-one + NADP+ + H2O
-
Substrates: -
Products: 51% conversion at 20 h
Products: 51% conversion at 20 h
?
2-phenylethyl methyl sulfide + NADPH + O2
2-phenylethyl methyl sulfoxide
-
Substrates: -
Products: -
Products: -
?
2-phenylpropyl methyl sulfide + NADPH + O2
2-phenylpropyl methyl sulfoxide
-
Substrates: -
Products: -
Products: -
?
2-propylcyclohexanone + NADPH + O2 + H+
(7S)-7-propyloxepan-2-one + NADP+ + H2O
-
Substrates: -
Products: -
Products: -
?
2-thiacyclohexanone + NADPH + O2
1-oxa-2-oxo-3-thiacycloheptane + NADP+ + H2O
-
Substrates: substrate inactivates enzyme after a few turnovers
Products: -
Products: -
?
3,3,5-trimethyl-cyclohexanone + NADPH + H+ + O2
trimethyl-epsilon-caprolactone + NADP+ + H2O
3,3,5-trimethylcyclohexanone + NADPH + H+ + O2
4,6,6-trimethyloxepan-2-one + 4,4,6-trimethyloxepan-2-one + NADP+ + H2O
Substrates: -
Products: -
Products: -
?
3,3,5-trimethylcyclohexanone + NADPH + O2 + H+
4,6,6-trimethyloxepan-2-one + 4,4,6-trimethyloxepan-2-one + NADP+ + H2O
3,4-dihydronaphthalen-2(1H)-one + NADPH + H+ + O2
8,9-dihydro-5H-7-oxa-benzocyclo-hepten-6-one + NADP+ + H2O
Substrates: -
Products: -
Products: -
?
3,4-dihydronaphthalen-2(1H)-one + NADPH + O2 + H+
4,5-dihydro-3-benzoxepin-2(1H)-one + NADP+ + H2O
-
Substrates: -
Products: more than 95% conversion one isomer
Products: more than 95% conversion one isomer
?
3,5-dimethylcyclohexanone + NADPH + H+ + O2
4,6-dimethyloxepan-2-one + NADP+ + H2O
Substrates: less than 50% conversion, 90% enantiomeric excess, (-)-product
Products: -
Products: -
?
3-(1,3-benzodioxol-5-yl)cyclobutanone + NADPH + H+ + O2
4-(1,3-benzodioxol-5-yl)dihydrofuran-2(3H)-one + NADP+ + H2O
Substrates: more than 90% conversion,36% enantiomeric excess, (+)-product
Products: -
Products: -
?
3-(3,4,5-trimethoxyphenyl)cyclobutanone + NADPH + H+ + O2
4-(3,4,5-trimethoxyphenyl)dihydrofuran-2(3H)-one + NADP+ + H2O
Substrates: less than 50% conversion, 96% enantiomeric excess, (-)-product
Products: -
Products: -
?
3-methylcyclohexanone + NADPH + O2 + H+
(4S)-4-methyloxepan-2-one + (6R)-6-methyloxepan-2-one + NADP+ + H2O
-
Substrates: -
Products: -
Products: -
?
3-phenylcyclobutanone+ NADPH + H+ + O2
3-phenyloxolan-2-one + NADP+ + H2O
Substrates: -
Products: -
Products: -
?
3-phenylcyclohexanone + NADPH + H+ + O2
1-oxa-2-oxo-4-phenylcycloheptane + NADP+ + H2O
Substrates: -
Products: -
Products: -
?
3-phenylcyclopentanone + NADPH + H+ + O2
4-phenyloxan-2-one + NADP+ + H2O
Substrates: -
Products: -
Products: -
?
4,4-dimethylcyclohexanone + NADPH + H+ + O2
5,5-dimethyloxepan-2-one + NADP+ + H2O
Substrates: 50-90% conversion
Products: -
Products: -
?
4-(3-fluorophenyl)cyclohexanone + NADPH + H+ + O2
4-(3-fluorophenyl)hexano-6-lactone + NADP+ + H2O
Substrates: -
Products: -
Products: -
?
4-(3-methylphenyl)cyclohexanone + NADPH + H+ + O2
4-(3-methylphenyl)hexano-6-lactone + NADP+ + H2O
Substrates: -
Products: -
Products: -
?
4-(4-chlorophenyl)cyclohexanone + NADPH + H+ + O2
4-(4-chlorophenyl)hexano-6-lactone + NADP+ + H2O
Substrates: -
Products: -
Products: -
?
4-(4-fluorophenyl)cyclohexanone + NADPH + H+ + O2
4-(4-fluorophenyl)hexano-6-lactone + NADP+ + H2O
Substrates: -
Products: -
Products: -
?
4-(4-methoxyhenyl)cyclohexanone + NADPH + H+ + O2
4-(4-methoxyphenyl)hexano-6-lactone + NADP+ + H2O
Substrates: -
Products: -
Products: -
?
4-(4-methylphenyl)cyclohexanone + NADPH + H+ + O2
4-(4-methylphenyl)hexano-6-lactone + NADP+ + H2O
Substrates: -
Products: -
Products: -
?
4-allyl-cyclohexanone + NADPH + O2
4-allyl-hexano-6-lactone + NADP+ + H2O
-
Substrates: -
Products: -
Products: -
?
4-bromocyclohexanone + NADPH + O2
4-bromo-hexano-6-lactone + NADP+ + H2O
-
Substrates: -
Products: -
Products: -
?
4-chlorocyclohexanone + NADPH + O2
4-chloro-hexano-6-lactone + NADP+ + H2O
-
Substrates: -
Products: -
Products: -
?
4-ethoxy-cyclohexanone + NADPH + O2
4-ethoxy-hexano-6-lactone + NADP+ + H2O
-
Substrates: -
Products: -
Products: -
?
4-ethyl-cyclohexanone + NADPH + O2
4-ethyl-hexano-6-lactone + NADP+ + H2O
-
Substrates: -
Products: -
Products: -
?
4-ethylcyclohexanone + NADPH + H+ + O2
4-ethylhexano-6-lactone + NADP+ + H2O
Substrates: -
Products: -
Products: -
?
4-iodocyclohexanone + NADPH + O2
4-iodo-hexano-6-lactone + NADP+ + H2O
-
Substrates: -
Products: -
Products: -
?
4-methoxy-cyclohexanone + NADPH + O2
4-methoxy-hexano-6-lactone + NADP+ + H2O
-
Substrates: -
Products: -
Products: -
?
4-methyl-cyclohexanone + NADPH + O2
4-methyl-hexano-6-lactone + NADP+ + H2O
-
Substrates: -
Products: -
Products: -
?
4-methylcyclohexanone + NADPH + H+ + O2
4-methylhexano-6-lactone + NADP+ + H2O
Substrates: -
Products: -
Products: -
?
4-methylcyclohexanone + NADPH + H+ + O2
?
Substrates: -
Products: -
Products: -
?
4-n-propyl-cyclohexanone + NADPH + O2
4-n-propyl-hexano-6-lactone + NADP+ + H2O
-
Substrates: -
Products: -
Products: -
?
4-pentylcyclohexanone + NADPH + H+ + O2
4-pentylhexano-6-lactone + NADP+ + H2O
Substrates: -
Products: -
Products: -
?
4-phenylcyclohexanone + NADPH + H+ + O2
4-phenylhexano-6-lactone + NADP+ + H2O
Substrates: -
Products: -
Products: -
?
4-phenylcyclohexanone + NADPH + H+ + O2
5-phenyloxepan-2-one + NADP+ + H2O
Substrates: less than 50% conversion, 97% enantiomeric excess, (-)-product
Products: -
Products: -
?
4-propylcyclohexanone + NADPH + H+ + O2
4-propylhexano-6-lactone + NADP+ + H2O
Substrates: -
Products: -
Products: -
?
4-tert-butylcyclohexanone + NADPH + H+ + O2
5-t-butyl-2-oxepanone + NADP+ + H2O
Substrates: -
Products: -
Products: -
?
4-tert-butylcyclohexanone + NADPH + O2
1-oxa-2-oxo-5-tert-butylcycloheptane + NADP+ + H2O
-
Substrates: slight
Products: -
Products: -
?
4-tert-butylcyclohexanone + NADPH + O2 + H+
(5S)-5-tert-butyloxepan-2-one + NADP+ + H2O
-
Substrates: -
Products: 88% conversion at 20 h, 99% enantiomeric excess
Products: 88% conversion at 20 h, 99% enantiomeric excess
?
4a-methyltetrahydro-1aH-naphtho[1,8a-b]oxirene-2,5(3H,6H)-dione + NADPH + O2
(1R,3S,7S)-7-methyl-2,8-dioxatricyclo[5.5.0.01,3]dodecane-4,9-dione + NADP+ + H2O
5-methoxy-2-methylthio-1H-benzimidazole + NADPH + H+ + O2
?
-
Substrates: poor substrate for wild-type
Products: -
Products: -
?
beta-tetralonne + NADPH + H+ + O2
? + NADP+ + H2O
Substrates: 25% conversion efficincy, purified enzyme
Products: -
Products: -
?
bicyclo[3.2.0]hept-2-en-6-one + NADPH + H+ + O2
(1R,5S)-3-oxabicyclo-[3.3.0]oct-6-en-3-one + (1S,5R)-2-oxabicyclo-[3.3.0]oct-6-en-3-one + NADP+ + H2O
bicyclo[3.2.0]hept-2-en-6-one + NADPH + H+ + O2
3,3a,6,6a-tetrahydro-1H-cyclopenta[c]furan-1-one + NADP+ + H2O
Substrates: 63% of the activity with cyclohexanone
Products: -
Products: -
?
cis-hex-2-enyl phenyl selenide + NADPH + O2
?
-
Substrates: -
Products: -
Products: -
?
cyclobutanone + NADPH + H+ + O2
dihydrofuran-2(3H)-one + NADP+ + H2O
Substrates: 65% of the activity with cyclohexanone
Products: -
Products: -
?
cyclobutyl methyl ketone + NADPH + O2
? + NADP+ + H2O
Substrates: 17.5% of the activity with cyclohexanone
Products: -
Products: -
?
cyclodecanone + NADPH + O2
1-oxa-2-oxocycloendecane + NADP+ + H2O
-
Substrates: low activity
Products: -
Products: -
?
cyclohexyl methyl ketone + NADPH + O2
? + NADP+ + H2O
Substrates: 15.7% of the activity with cyclohexanone
Products: -
Products: -
?
cyclohexyl methyl sulfide + NADPH + O2
cyclohexyl methyl sulfoxide + NADP+ + H2O
-
Substrates: -
Products: -
Products: -
?
cyclopentyl methyl sulfide + NADPH + O2
cyclopentyl methyl sulfoxide + NADP+ + H2O
-
Substrates: -
Products: -
Products: -
?
delta-thiovalerolactone + NADPH + O2
?
-
Substrates: substrate inactivates enzyme after a few turnovers
Products: -
Products: -
ir
dithiane + NADPH + H+ + O2
(R)-dithiane sulfoxide + NADP+ + H2O
-
Substrates: recombinant enzyme in E. coli or Saccharomyces cerevisiae
Products: -
Products: -
?
epsilon-thiocaprolactone + NADPH + O2
?
-
Substrates: substrate inactivates enzyme after a few turnovers
Products: -
Products: -
ir
ethyl 4-oxocyclohexanecarboxylate + NADPH + H+ + O2
ethyl 7-oxooxepane-4-carboxylate + NADP+ + H2O
Substrates: less than 50% conversion, 98% enantiomeric excess, (-)-product
Products: -
Products: -
?
ethyl p-tolyl sulfide + NADPH + O2
(S)-ethyl p-tolyl sulfoxide + NADP+ + H2O
-
Substrates: -
Products: -
Products: -
?
ethylene monothiocarbonate + NADPH + O2
?
-
Substrates: substrate inactivates enzyme after a few turnovers
Products: -
Products: -
?, ir
gamma-thiobutyrolactone + NADPH + O2
?
-
Substrates: substrate inactivates enzyme after a few turnovers
Products: -
Products: -
ir
methyl phenyl sulfoxide + NADPH + H+ + O2
? + NADP+ + H2O
Substrates: 55% conversion efficincy, purified enzyme
Products: -
Products: -
?
n-butyl methyl sulfide + NADPH + O2
?
-
Substrates: recombinant enzyme in E. coli or Saccharomyces cerevisiae
Products: -
Products: -
?
n-butylboronic acid + NADPH + O2
n-butanol + BO3- + NADP+ + H2O
-
Substrates: -
Products: -
Products: -
?
n-octylboronic acid + NADPH + O2
n-octanol + BO3- + NADP+ + H2O
-
Substrates: -
Products: -
Products: -
?
norcamphor + NADPH + O2
? + NADP+ + H2O
Substrates: 74.8% of the activity with cyclohexanone
Products: -
Products: -
?
octahydronaphthalen-1(2H)-one + NADPH + H+ + O2
octahydro-benzo[b]oxepin-2-one + octahydro-benzo[c]oxepin-1-one + NADP+ + H2O
Substrates: -
Products: -
Products: -
?
octahydronaphthalen-1(2H)-one + NADPH + O2 + H+
octahydro-1-benzoxepin-2(3H)-one + octahydro-2-benzoxepin-1(3H)-one + NADP+ + H2O
-
Substrates: -
Products: 100% conversion two isomers octahydro-1-benzoxepin-2(3H)-one + octahydro-2-benzoxepin-1(3H)-one with ratio 2/1
Products: 100% conversion two isomers octahydro-1-benzoxepin-2(3H)-one + octahydro-2-benzoxepin-1(3H)-one with ratio 2/1
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octahydronaphthalen-2(1H)-one + NADPH + H+ + O2
cis-octahydro-benzo[c]oxepin-3-one + trans-octahydro-benzo[c]oxepin-3-one + cis-octahydro-7-oxa-benzocyclohepten-6-one + NADP+ + H2O
Substrates: -
Products: -
Products: -
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octahydronaphthalen-2(1H)-one + NADPH + O2 + H+
octahydro-3-benzoxepin-2(1H)-one + octahydro-2-benzoxepin-3(1H)-one + NADP+ + H2O
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Substrates: -
Products: 66% conversion at 20 h, octahydro-2-benzoxepin-3(1H)-one is the major product
Products: 66% conversion at 20 h, octahydro-2-benzoxepin-3(1H)-one is the major product
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omeprazole sulfide + NADPH + H+ + O2
(S)-omeprazole + NADP+ + H2O
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Substrates: no substrae for wild-type
Products: -
Products: -
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phenylboronic acid + NADPH + O2
phenol + BO3- + NADP+ + H2O
-
Substrates: -
Products: -
Products: -
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pyrmetazole + NADPH + H+ + O2
pyrmetazole (S)-sulfoxide + NADP+ + H2O
Substrates: -
Products: -
Products: -
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S-gamma-thiobutyrolactone + NADPH + O2
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Substrates: substrate irreversibly inactivates enzyme after a few turnovers
Products: -
Products: -
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syn-7-benzyloxymethyl-2-norbonen-5-one + NADPH + O2
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-
Substrates: -
Products: -
Products: -
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tert-butyl ethyl sulfide + NADPH + O2
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-
Substrates: low activity
Products: -
Products: -
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thioanisole + NADPH + H+ + O2
(R)-methyl phenyl sulfoxide + NADP+ + H2O
Substrates: -
Products: -
Products: -
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trans-hex-2-enyl phenyl selenide + NADPH + O2
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-
Substrates: -
Products: -
Products: -
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[(2-chloroethyl)sulfanyl]benzene + NADPH + H+ + O2
(R)-2-chloroethyl phenyl sulfoxide + NADP+ + H2O
Substrates: -
Products: -
Products: -
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[(2-hydroxyethyl)sulfanyl]benzene + NADPH + H+ + O2
(R)-2-hydroxyethyl phenyl sulfoxide + NADP+ + H2O
Substrates: -
Products: -
Products: -
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(1aS,4aS,8aS)-8a-methylhexahydronaphthalene-1,6-dione + NADPH + O2
(5aR,9aS)-9a-methylhexahydrobenzo[b]oxepine-2,7-dione + NADP+ + H2O
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Substrates: WielandMiescher ketone, no activity with the (1aR,4aR,8aR)-stereoisomer, stereoselective formation of the cis-(5aR,9aS)-isomer
Products: -
Products: -
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(1aS,4aS,8aS)-8a-methylhexahydronaphthalene-1,6-dione + NADPH + O2
(5aR,9aS)-9a-methylhexahydrobenzo[b]oxepine-2,7-dione + NADP+ + H2O
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Substrates: WielandMiescher ketone, no activity with the (1aR,4aR,8aR)-stereoisomer, stereoselective formation of the cis-(5aR,9aS)-isomer
Products: -
Products: -
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(2R,6S)-2,6-dimethylcyclohexanone + NADPH + O2 + H+
(3R,7S)-3,7-dimethyloxepan-2-one + NADP+ + H2O
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Substrates: -
Products: 90% conversion at 20 h, 99% enantiomeric excess
Products: 90% conversion at 20 h, 99% enantiomeric excess
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(2R,6S)-2,6-dimethylcyclohexanone + NADPH + O2 + H+
(3R,7S)-3,7-dimethyloxepan-2-one + NADP+ + H2O
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Substrates: -
Products: 90% conversion at 20 h, 99% enantiomeric excess
Products: 90% conversion at 20 h, 99% enantiomeric excess
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(3R)-3-(1-methylethenyl)cyclohexanone + NADPH + O2 + H+
(6S)-6-(1-methylethenyl)oxepan-2-one + NADP+ + H2O
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Substrates: -
Products: 99% regioselectivity
Products: 99% regioselectivity
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(3R)-3-(1-methylethenyl)cyclohexanone + NADPH + O2 + H+
(6S)-6-(1-methylethenyl)oxepan-2-one + NADP+ + H2O
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Substrates: -
Products: 99% regioselectivity
Products: 99% regioselectivity
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(4aR,8aS)-8a-methylhexahydronaphthalene-1,6(2H,5H)-dione + NADPH + O2
(5aR,9aS)-9a-methylhexahydrobenzo[b]oxepine-2,7-dione + (4aS,6S,8aR)-6-hydroxy-8a-methyloctahydronaphthalen-1-one + NADP+ + H2O
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Substrates: -
Products: -
Products: -
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(4aR,8aS)-8a-methylhexahydronaphthalene-1,6(2H,5H)-dione + NADPH + O2
(5aR,9aS)-9a-methylhexahydrobenzo[b]oxepine-2,7-dione + (4aS,6S,8aR)-6-hydroxy-8a-methyloctahydronaphthalen-1-one + NADP+ + H2O
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Substrates: -
Products: -
Products: -
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(ethylsulfanyl)benzene + NADPH + H+ + O2
(R)-ethyl phenyl sulfoxide + NADP+ + H2O
Substrates: -
Products: -
Products: -
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(ethylsulfanyl)benzene + NADPH + H+ + O2
(R)-ethyl phenyl sulfoxide + NADP+ + H2O
Substrates: -
Products: -
Products: -
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(propylsulfanyl)benzene + NADPH + H+ + O2
(R)-propyl phenyl sulfoxide + NADP+ + H2O
Substrates: -
Products: -
Products: -
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(propylsulfanyl)benzene + NADPH + H+ + O2
(R)-propyl phenyl sulfoxide + NADP+ + H2O
Substrates: -
Products: -
Products: -
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1,2-cyclohexandione + NADPH + H+ + O2
? + NADP+ + H2O
Substrates: 18% of the activity with cyclohexanone
Products: -
Products: -
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1,2-cyclohexandione + NADPH + H+ + O2
? + NADP+ + H2O
Substrates: 7% of the activity with cyclohexanone
Products: -
Products: -
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1,2-cyclohexandione + NADPH + H+ + O2
? + NADP+ + H2O
Substrates: 7% of the activity with cyclohexanone
Products: -
Products: -
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1,2-cyclohexandione + NADPH + H+ + O2
? + NADP+ + H2O
Substrates: 18% of the activity with cyclohexanone
Products: -
Products: -
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1,2-cyclohexandione + NADPH + H+ + O2
? + NADP+ + H2O
Substrates: 2% of the activity with cyclohexanone
Products: -
Products: -
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1,2-cyclohexandione + NADPH + H+ + O2
? + NADP+ + H2O
Substrates: 24% of the activity with cyclohexanone
Products: -
Products: -
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1,2-cyclohexandione + NADPH + H+ + O2
? + NADP+ + H2O
Substrates: 2% of the activity with cyclohexanone
Products: -
Products: -
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1,2-cyclohexandione + NADPH + H+ + O2
? + NADP+ + H2O
Substrates: 24% of the activity with cyclohexanone
Products: -
Products: -
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1,3-cyclohexandione + NADPH + H+ + O2
? + NADP+ + H2O
Substrates: 11% of the activity with cyclohexanone
Products: -
Products: -
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1,3-cyclohexandione + NADPH + H+ + O2
? + NADP+ + H2O
Substrates: 5% of the activity with cyclohexanone
Products: -
Products: -
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1,3-cyclohexandione + NADPH + H+ + O2
? + NADP+ + H2O
Substrates: 11% of the activity with cyclohexanone
Products: -
Products: -
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1,3-cyclohexandione + NADPH + H+ + O2
? + NADP+ + H2O
Substrates: 5% of the activity with cyclohexanone
Products: -
Products: -
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1,3-cyclohexandione + NADPH + H+ + O2
? + NADP+ + H2O
Substrates: 4% of the activity with cyclohexanone
Products: -
Products: -
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1,3-cyclohexandione + NADPH + H+ + O2
? + NADP+ + H2O
Substrates: 4% of the activity with cyclohexanone
Products: -
Products: -
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1,3-cyclohexandione + NADPH + H+ + O2
? + NADP+ + H2O
Substrates: 4% of the activity with cyclohexanone
Products: -
Products: -
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