1.14.13.22: cyclohexanone monooxygenase
This is an abbreviated version!
For detailed information about cyclohexanone monooxygenase, go to the full flat file.
Word Map on EC 1.14.13.22
-
1.14.13.22
-
baeyer-villiger
-
acinetobacter
-
lactones
-
bvmos
-
ncimb
-
calcoaceticus
-
cyclohexanol
-
synthesis
-
criegee
-
epsilon-caprolactone
-
c4a-peroxyflavin
-
biooxidation
-
bicyclo3.2.0hept-2-en-6-one
-
phenylacetone
-
cyclopentanone
-
biotechnology
- 1.14.13.22
-
baeyer-villiger
- acinetobacter
- lactones
-
bvmos
-
ncimb
- calcoaceticus
- cyclohexanol
- synthesis
-
criegee
- epsilon-caprolactone
-
c4a-peroxyflavin
-
biooxidation
-
bicyclo3.2.0hept-2-en-6-one
- phenylacetone
- cyclopentanone
- biotechnology
Reaction
Synonyms
Bpro_556, CAMO, CHMO, ChnB, chnB protein, chnB1 protein, CHXON, CMO, cycloalkaone monooxygenase, cyclohexanone 1, 2-mono-oxygenase, cyclohexanone mono-oxygenase, cyclohexanone monooxygenase, cyclohexanone oxygenase, cyclohexanone:NADPH:oxygen oxidoreductase (lactone-forming), oxygenase, cyclohexanone mono-
ECTree
1.14.13.22 cyclohexanone monooxygenaseAdvanced search results
results (
results (Substrates Products
Substrates Products on EC 1.14.13.22 - cyclohexanone monooxygenase
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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
(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
74.4% of the activity with cyclohexanone
-
-
?
(2R)-2-ethylcyclohexanone + NADPH + H+ + O2
(7S)-7-ethyloxepan-2-one + NADP+ + H2O
92% conversion, 30% enantiomeric excess, (-)-product
-
-
?
(2R,6S)-2,6-dimethylcyclohexanone + NADPH + H+ + O2
cis-3, 7-dimethyl-2-oxepanone + NADP+ + H2O
-
-
-
?
(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
75% conversion, 99% enantiomeric excess, (-)-product
-
-
?
(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
?
-
recombinant enzyme in E. coli or Saccharomyces cerevisiae
-
-
?
1,4-dioxaspiro[4.5]decan-8-one + NADPH + H+ + O2
1,4,8-trioxa-spiro[4,6]undecan-9-one + NADP+ + H2O
-
-
-
?
1,4-dioxaspiro[4.5]decan-8-one + NADPH + O2 + H+
1,4,8-trioxaspiro[4.6]undecan-9-one + NADP+ + H2O
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
-
-
-
?
2-(methylsulfanyl)naphthalene + NADPH + H+ + O2
2-(methanesulfinyl)naphthalene + NADP+ + H2O
2-hexylcyclopentanone + NADPH + H+ + O2
6-hexyl-tetrahydro-pyran-2-one + NADP+ + H2O
-
-
-
?
2-hexylcyclopentanone + NADPH + O2 + H+
6-hexyltetrahydro-2H-pyran-2-one + NADP+ + H2O
-
-
82% conversion at 20 h
-
?
2-hydroxycyclobutanone + NADPH + H+ + O2
1-oxa-2-oxo-3-hydroxycyclopentane + NADP+ + H2O
67.3% of the activity with cyclohexanone
-
-
?
2-hydroxyethyl methyl sulfide + NADPH + O2
2-hydroxyethyl methyl sulfoxide + NADP+ + H2O
-
-
-
-
?
2-methylcyclohexanone + NADPH + O2 + H+
7-methyloxepan-2-one + NADP+ + H2O
-
-
-
-
?
2-methylcyclohexyl boronic acid + NADPH + O2
2-methylcyclohexanol + BO3- + NADP+ + H2O
-
racemic substrate
-
?
2-phenylcyclohexanone + NADPH + H+ + O2
3-phenyloxepan-2-one + NADP+ + H2O
-
-
-
?
2-phenylcyclohexanone + NADPH + O2
1-oxa-2-oxo-3-phenylcycloheptane + NADP+ + H2O
-
slight
-
-
?
2-phenylcyclohexanone + NADPH + O2 + H+
7-phenyloxepan-2-one + NADP+ + H2O
-
-
51% conversion at 20 h
-
?
2-phenylethyl methyl sulfide + NADPH + O2
2-phenylethyl methyl sulfoxide
-
-
-
?
2-phenylpropyl methyl sulfide + NADPH + O2
2-phenylpropyl methyl sulfoxide
-
-
-
?
2-propylcyclohexanone + NADPH + O2 + H+
(7S)-7-propyloxepan-2-one + NADP+ + H2O
-
-
-
-
?
2-thiacyclohexanone + NADPH + O2
1-oxa-2-oxo-3-thiacycloheptane + NADP+ + H2O
-
substrate inactivates enzyme after a few turnovers
-
-
?
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
-
-
-
?
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
-
-
-
?
3,4-dihydronaphthalen-2(1H)-one + NADPH + O2 + H+
4,5-dihydro-3-benzoxepin-2(1H)-one + NADP+ + H2O
-
-
more than 95% conversion one isomer
-
?
3,5-dimethylcyclohexanone + NADPH + H+ + O2
4,6-dimethyloxepan-2-one + NADP+ + H2O
less than 50% conversion, 90% enantiomeric excess, (-)-product
-
-
?
3-(1,3-benzodioxol-5-yl)cyclobutanone + NADPH + H+ + O2
4-(1,3-benzodioxol-5-yl)dihydrofuran-2(3H)-one + NADP+ + H2O
more than 90% conversion,36% enantiomeric excess, (+)-product
-
-
?
3-(3,4,5-trimethoxyphenyl)cyclobutanone + NADPH + H+ + O2
4-(3,4,5-trimethoxyphenyl)dihydrofuran-2(3H)-one + NADP+ + H2O
less than 50% conversion, 96% enantiomeric excess, (-)-product
-
-
?
3-methylcyclohexanone + NADPH + O2 + H+
(4S)-4-methyloxepan-2-one + (6R)-6-methyloxepan-2-one + NADP+ + H2O
-
-
-
-
?
3-phenylcyclobutanone+ NADPH + H+ + O2
3-phenyloxolan-2-one + NADP+ + H2O
-
-
-
?
3-phenylcyclohexanone + NADPH + H+ + O2
1-oxa-2-oxo-4-phenylcycloheptane + NADP+ + H2O
-
-
-
?
3-phenylcyclopentanone + NADPH + H+ + O2
4-phenyloxan-2-one + NADP+ + H2O
-
-
-
?
4,4-dimethylcyclohexanone + NADPH + H+ + O2
5,5-dimethyloxepan-2-one + NADP+ + H2O
50-90% conversion
-
-
?
4-(3-fluorophenyl)cyclohexanone + NADPH + H+ + O2
4-(3-fluorophenyl)hexano-6-lactone + NADP+ + H2O
-
-
-
?
4-(3-methylphenyl)cyclohexanone + NADPH + H+ + O2
4-(3-methylphenyl)hexano-6-lactone + NADP+ + H2O
-
-
-
?
4-(4-chlorophenyl)cyclohexanone + NADPH + H+ + O2
4-(4-chlorophenyl)hexano-6-lactone + NADP+ + H2O
-
-
-
?
4-(4-fluorophenyl)cyclohexanone + NADPH + H+ + O2
4-(4-fluorophenyl)hexano-6-lactone + NADP+ + H2O
-
-
-
?
4-(4-methoxyhenyl)cyclohexanone + NADPH + H+ + O2
4-(4-methoxyphenyl)hexano-6-lactone + NADP+ + H2O
-
-
-
?
4-(4-methylphenyl)cyclohexanone + NADPH + H+ + O2
4-(4-methylphenyl)hexano-6-lactone + NADP+ + H2O
-
-
-
?
4-allyl-cyclohexanone + NADPH + O2
4-allyl-hexano-6-lactone + NADP+ + H2O
-
-
-
-
?
4-bromocyclohexanone + NADPH + O2
4-bromo-hexano-6-lactone + NADP+ + H2O
-
-
-
-
?
4-chlorocyclohexanone + NADPH + O2
4-chloro-hexano-6-lactone + NADP+ + H2O
-
-
-
-
?
4-ethoxy-cyclohexanone + NADPH + O2
4-ethoxy-hexano-6-lactone + NADP+ + H2O
-
-
-
-
?
4-ethyl-cyclohexanone + NADPH + O2
4-ethyl-hexano-6-lactone + NADP+ + H2O
-
-
-
-
?
4-ethylcyclohexanone + NADPH + H+ + O2
4-ethylhexano-6-lactone + NADP+ + H2O
-
-
-
?
4-iodocyclohexanone + NADPH + O2
4-iodo-hexano-6-lactone + NADP+ + H2O
-
-
-
-
?
4-methoxy-cyclohexanone + NADPH + O2
4-methoxy-hexano-6-lactone + NADP+ + H2O
-
-
-
-
?
4-methyl-cyclohexanone + NADPH + O2
4-methyl-hexano-6-lactone + NADP+ + H2O
-
-
-
-
?
4-methylcyclohexanone + NADPH + H+ + O2
4-methylhexano-6-lactone + NADP+ + H2O
-
-
-
?
4-n-propyl-cyclohexanone + NADPH + O2
4-n-propyl-hexano-6-lactone + NADP+ + H2O
-
-
-
-
?
4-pentylcyclohexanone + NADPH + H+ + O2
4-pentylhexano-6-lactone + NADP+ + H2O
-
-
-
?
4-phenylcyclohexanone + NADPH + H+ + O2
4-phenylhexano-6-lactone + NADP+ + H2O
-
-
-
?
4-phenylcyclohexanone + NADPH + H+ + O2
5-phenyloxepan-2-one + NADP+ + H2O
less than 50% conversion, 97% enantiomeric excess, (-)-product
-
-
?
4-propylcyclohexanone + NADPH + H+ + O2
4-propylhexano-6-lactone + NADP+ + H2O
-
-
-
?
4-tert-butylcyclohexanone + NADPH + H+ + O2
5-t-butyl-2-oxepanone + NADP+ + H2O
-
-
-
?
4-tert-butylcyclohexanone + NADPH + O2
1-oxa-2-oxo-5-tert-butylcycloheptane + NADP+ + H2O
-
slight
-
-
?
4-tert-butylcyclohexanone + NADPH + O2 + H+
(5S)-5-tert-butyloxepan-2-one + NADP+ + H2O
-
-
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
?
-
poor substrate for wild-type
-
-
?
beta-tetralonne + NADPH + H+ + O2
? + NADP+ + H2O
25% conversion efficincy, purified enzyme
-
-
?
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
63% of the activity with cyclohexanone
-
-
?
cyclobutanone + NADPH + H+ + O2
dihydrofuran-2(3H)-one + NADP+ + H2O
65% of the activity with cyclohexanone
-
-
?
cyclobutyl methyl ketone + NADPH + O2
? + NADP+ + H2O
17.5% of the activity with cyclohexanone
-
-
?
cyclodecanone + NADPH + O2
1-oxa-2-oxocycloendecane + NADP+ + H2O
-
low activity
-
-
?
cyclohexyl methyl ketone + NADPH + O2
? + NADP+ + H2O
15.7% of the activity with cyclohexanone
-
-
?
cyclohexyl methyl sulfide + NADPH + O2
cyclohexyl methyl sulfoxide + NADP+ + H2O
-
-
-
?
cyclopentyl methyl sulfide + NADPH + O2
cyclopentyl methyl sulfoxide + NADP+ + H2O
-
-
-
?
delta-thiovalerolactone + NADPH + O2
?
-
substrate inactivates enzyme after a few turnovers
-
-
ir
dithiane + NADPH + H+ + O2
(R)-dithiane sulfoxide + NADP+ + H2O
-
recombinant enzyme in E. coli or Saccharomyces cerevisiae
-
?
epsilon-thiocaprolactone + NADPH + O2
?
-
substrate inactivates enzyme after a few turnovers
-
-
ir
ethyl 4-oxocyclohexanecarboxylate + NADPH + H+ + O2
ethyl 7-oxooxepane-4-carboxylate + NADP+ + H2O
less than 50% conversion, 98% enantiomeric excess, (-)-product
-
-
?
ethylene monothiocarbonate + NADPH + O2
?
-
substrate inactivates enzyme after a few turnovers
-
-
?, ir
gamma-thiobutyrolactone + NADPH + O2
?
-
substrate inactivates enzyme after a few turnovers
-
-
ir
methyl phenyl sulfoxide + NADPH + H+ + O2
? + NADP+ + H2O
55% conversion efficincy, purified enzyme
-
-
?
n-butyl methyl sulfide + NADPH + O2
?
-
recombinant enzyme in E. coli or Saccharomyces cerevisiae
-
-
?
norcamphor + NADPH + O2
? + NADP+ + H2O
74.8% of the activity with cyclohexanone
-
-
?
octahydronaphthalen-1(2H)-one + NADPH + H+ + O2
octahydro-benzo[b]oxepin-2-one + octahydro-benzo[c]oxepin-1-one + NADP+ + H2O
-
-
-
?
octahydronaphthalen-1(2H)-one + NADPH + O2 + H+
octahydro-1-benzoxepin-2(3H)-one + octahydro-2-benzoxepin-1(3H)-one + NADP+ + H2O
-
-
100% conversion two isomers octahydro-1-benzoxepin-2(3H)-one + octahydro-2-benzoxepin-1(3H)-one with ratio 2/1
-
?
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
-
-
-
?
octahydronaphthalen-2(1H)-one + NADPH + O2 + H+
octahydro-3-benzoxepin-2(1H)-one + octahydro-2-benzoxepin-3(1H)-one + NADP+ + H2O
-
-
66% conversion at 20 h, octahydro-2-benzoxepin-3(1H)-one is the major product
-
?
omeprazole sulfide + NADPH + H+ + O2
(S)-omeprazole + NADP+ + H2O
-
no substrae for wild-type
-
-
?
pyrmetazole + NADPH + H+ + O2
pyrmetazole (S)-sulfoxide + NADP+ + H2O
-
-
-
?
S-gamma-thiobutyrolactone + NADPH + O2
?
-
substrate irreversibly inactivates enzyme after a few turnovers
-
-
?
thioanisole + NADPH + H+ + O2
(R)-methyl phenyl sulfoxide + NADP+ + H2O
-
-
-
?
[(2-chloroethyl)sulfanyl]benzene + NADPH + H+ + O2
(R)-2-chloroethyl phenyl sulfoxide + NADP+ + H2O
-
-
-
?
[(2-hydroxyethyl)sulfanyl]benzene + NADPH + H+ + O2
(R)-2-hydroxyethyl phenyl sulfoxide + NADP+ + H2O
-
-
-
?
(1aS,4aS,8aS)-8a-methylhexahydronaphthalene-1,6-dione + NADPH + O2
(5aR,9aS)-9a-methylhexahydrobenzo[b]oxepine-2,7-dione + NADP+ + H2O
-
WielandMiescher ketone, no activity with the (1aR,4aR,8aR)-stereoisomer, stereoselective formation of the cis-(5aR,9aS)-isomer
-
-
?
(1aS,4aS,8aS)-8a-methylhexahydronaphthalene-1,6-dione + NADPH + O2
(5aR,9aS)-9a-methylhexahydrobenzo[b]oxepine-2,7-dione + NADP+ + H2O
-
WielandMiescher ketone, no activity with the (1aR,4aR,8aR)-stereoisomer, stereoselective formation of the cis-(5aR,9aS)-isomer
-
-
?
(2R,6S)-2,6-dimethylcyclohexanone + NADPH + O2 + H+
(3R,7S)-3,7-dimethyloxepan-2-one + NADP+ + H2O
-
-
90% conversion at 20 h, 99% enantiomeric excess
-
?
(2R,6S)-2,6-dimethylcyclohexanone + NADPH + O2 + H+
(3R,7S)-3,7-dimethyloxepan-2-one + NADP+ + H2O
-
-
90% conversion at 20 h, 99% enantiomeric excess
-
?
(3R)-3-(1-methylethenyl)cyclohexanone + NADPH + O2 + H+
(6S)-6-(1-methylethenyl)oxepan-2-one + NADP+ + H2O
-
-
99% regioselectivity
-
?
(3R)-3-(1-methylethenyl)cyclohexanone + NADPH + O2 + H+
(6S)-6-(1-methylethenyl)oxepan-2-one + NADP+ + H2O
-
-
99% regioselectivity
-
?
(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
-
-
-
-
?
(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
-
-
-
-
?
(ethylsulfanyl)benzene + NADPH + H+ + O2
(R)-ethyl phenyl sulfoxide + NADP+ + H2O
-
-
-
?
(ethylsulfanyl)benzene + NADPH + H+ + O2
(R)-ethyl phenyl sulfoxide + NADP+ + H2O
-
-
-
?
(propylsulfanyl)benzene + NADPH + H+ + O2
(R)-propyl phenyl sulfoxide + NADP+ + H2O
-
-
-
?
(propylsulfanyl)benzene + NADPH + H+ + O2
(R)-propyl phenyl sulfoxide + NADP+ + H2O
-
-
-
?
1,2-cyclohexandione + NADPH + H+ + O2
? + NADP+ + H2O
18% of the activity with cyclohexanone
-
-
?
1,2-cyclohexandione + NADPH + H+ + O2
? + NADP+ + H2O
7% of the activity with cyclohexanone
-
-
?
1,2-cyclohexandione + NADPH + H+ + O2
? + NADP+ + H2O
7% of the activity with cyclohexanone
-
-
?
1,2-cyclohexandione + NADPH + H+ + O2
? + NADP+ + H2O
18% of the activity with cyclohexanone
-
-
?
1,2-cyclohexandione + NADPH + H+ + O2
? + NADP+ + H2O
2% of the activity with cyclohexanone
-
-
?
1,2-cyclohexandione + NADPH + H+ + O2
? + NADP+ + H2O
24% of the activity with cyclohexanone
-
-
?
1,2-cyclohexandione + NADPH + H+ + O2
? + NADP+ + H2O
2% of the activity with cyclohexanone
-
-
?
1,2-cyclohexandione + NADPH + H+ + O2
? + NADP+ + H2O
24% of the activity with cyclohexanone
-
-
?
1,3-cyclohexandione + NADPH + H+ + O2
? + NADP+ + H2O
11% of the activity with cyclohexanone
-
-
?
1,3-cyclohexandione + NADPH + H+ + O2
? + NADP+ + H2O
5% of the activity with cyclohexanone
-
-
?
1,3-cyclohexandione + NADPH + H+ + O2
? + NADP+ + H2O
11% of the activity with cyclohexanone
-
-
?
1,3-cyclohexandione + NADPH + H+ + O2
? + NADP+ + H2O
5% of the activity with cyclohexanone
-
-
?
1,3-cyclohexandione + NADPH + H+ + O2
? + NADP+ + H2O
4% of the activity with cyclohexanone
-
-
?
1,3-cyclohexandione + NADPH + H+ + O2
? + NADP+ + H2O
4% of the activity with cyclohexanone
-
-
?
1,3-cyclohexandione + NADPH + H+ + O2
? + NADP+ + H2O
4% of the activity with cyclohexanone
-
-
?
1,3-dithiane + NADPH + O2
(R)-1,3-dithiane-1-oxide + NADP+ + H2O
-
-
-
-
?
1,3-dithiane + NADPH + O2
(R)-1,3-dithiane-1-oxide + NADP+ + H2O
-
-
-
-
?
1,4-cyclohexandione + NADPH + H+ + O2
? + NADP+ + H2O
112% of the activity with cyclohexanone
-
-
?
1,4-cyclohexandione + NADPH + H+ + O2
? + NADP+ + H2O
78% of the activity with cyclohexanone
-
-
?
1,4-cyclohexandione + NADPH + H+ + O2
? + NADP+ + H2O
112% of the activity with cyclohexanone
-
-
?
1,4-cyclohexandione + NADPH + H+ + O2
? + NADP+ + H2O
164% of the activity with cyclohexanone
-
-
?
1,4-cyclohexandione + NADPH + H+ + O2
? + NADP+ + H2O
90% of the activity with cyclohexanone
-
-
?
1,4-cyclohexandione + NADPH + H+ + O2
? + NADP+ + H2O
90% of the activity with cyclohexanone
-
-
?
1,4-cyclohexandione + NADPH + H+ + O2
? + NADP+ + H2O
164% of the activity with cyclohexanone
-
-
?
1,4-dioxaspiro[4.5]decan-8-one + NADPH + O2 + H+
1,4,8-trioxaspiro[4.6]undecan-9-one + NADP+ + H2O
-
-
80% conversion at 20 h
-
?
1,4-dioxaspiro[4.5]decan-8-one + NADPH + O2 + H+
1,4,8-trioxaspiro[4.6]undecan-9-one + NADP+ + H2O
-
-
80% conversion at 20 h
-
?
2 thioanisole + NADPH + H+ + O2
(R)-thioanisole sulfoxide + (S)-thioanisole sulfoxide + 2 NADP+ + 2 H2O
the enzyme produces both enantiomers, leading to an ee of only 16% for the (R)-sulfoxide
-
-
?
2 thioanisole + NADPH + H+ + O2
(R)-thioanisole sulfoxide + (S)-thioanisole sulfoxide + 2 NADP+ + 2 H2O
the enzyme produces both enantiomers, leading to an ee of only 16% for the (R)-sulfoxide
-
-
?
2,2,6-trimethylcyclohexanone + NADPH + O2 + H+
3,7,7-trimethyloxepan-2-one + NADP+ + H2O
-
-
66% conversion at 20 h
-
?
2,2,6-trimethylcyclohexanone + NADPH + O2 + H+
3,7,7-trimethyloxepan-2-one + NADP+ + H2O
-
-
66% conversion at 20 h
-
?
2-(methylsulfanyl)naphthalene + NADPH + H+ + O2
2-(methanesulfinyl)naphthalene + NADP+ + H2O
-
-
-
?
2-(methylsulfanyl)naphthalene + NADPH + H+ + O2
2-(methanesulfinyl)naphthalene + NADP+ + H2O
-
-
-
?
2-butanone + NADPH + H+ + O2
ethyl acetate + NADP+ + H2O
-
the ratio between the products methyl propanoate and ethyl acetate was found to be about 3:7 in the absence of any cosolvent
-
-
?
2-butanone + NADPH + H+ + O2
ethyl acetate + NADP+ + H2O
-
the ratio between the products methyl propanoate and ethyl acetate was found to be about 3:7 in the absence of any cosolvent
-
-
?
2-butanone + NADPH + H+ + O2
ethyl acetate + NADP+ + H2O
the ratio between the products methyl propanoate and ethyl acetate was found to be about 3:7 in the absence of any cosolvent. The effect of various solvents at 15% concentration is inspected. The strongest effect on regioselectivity is observed with 2-methyl-1,3-dioxolane (15%), which leads to almost exclusive production of ethyl acetate. 1,3-Dioxane and 1,4-dioxane have a more moderate influence, since about 40% of the total product is methyl propanoate. 30% methanol or ethanol as cosolvents have a negligible effect on enzyme regioselectivity
-
-
?
2-butanone + NADPH + H+ + O2
ethyl acetate + NADP+ + H2O
the ratio between the products methyl propanoate and ethyl acetate was found to be about 3:7 in the absence of any cosolvent. The effect of various solvents at 15% concentration is inspected. The strongest effect on regioselectivity is observed with 2-methyl-1,3-dioxolane (15%), which leads to almost exclusive production of ethyl acetate. 1,3-Dioxane and 1,4-dioxane have a more moderate influence, since about 40% of the total product is methyl propanoate. 30% methanol or ethanol as cosolvents have a negligible effect on enzyme regioselectivity
-
-
?
2-butanone + NADPH + H+ + O2
methyl propanoate + NADP+ + H2O
-
-
-
-
?
2-butanone + NADPH + H+ + O2
methyl propanoate + NADP+ + H2O
-
the ratio between the products methyl propanoate and ethyl acetate was found to be about 3:7 in the absence of any cosolvent
-
-
?
2-butanone + NADPH + H+ + O2
methyl propanoate + NADP+ + H2O
the ratio between the products methyl propanoate and ethyl acetate was found to be about 3:7 in the absence of any cosolvent. The effect of various solvents at 15% concentration is inspected. The strongest effect on regioselectivity is observed with 2-methyl-1,3-dioxolane (15%), which leads to almost exclusive production of ethyl acetate. 1,3-Dioxane and 1,4-dioxane have a more moderate influence, since about 40% of the total product is methyl propanoate. 30% methanol or ethanol as cosolvents have a negligible effect on enzyme regioselectivity
-
-
?
2-chlorothioanisole + NADPH + H+ + O2
1-(methanesulfinyl)-2-chlorobenzene + NADP+ + H2O
-
-
-
?
2-chlorothioanisole + NADPH + H+ + O2
1-(methanesulfinyl)-2-chlorobenzene + NADP+ + H2O
-
-
-
?
2-hydroxycyclohexanone + NADPH + O2
1-oxa-2-oxo-3-hydroxycycloheptane + NADP+ + H2O
-
-
-
-
?
2-hydroxycyclohexanone + NADPH + O2
1-oxa-2-oxo-3-hydroxycycloheptane + NADP+ + H2O
-
-
-
-
?
2-hydroxycyclohexanone + NADPH + O2
1-oxa-2-oxo-3-hydroxycycloheptane + NADP+ + H2O
-
-
-
-
?
2-hydroxycyclohexanone + NADPH + O2
1-oxa-2-oxo-3-hydroxycycloheptane + NADP+ + H2O
-
-
-
-
?
2-hydroxycyclohexanone + NADPH + O2
1-oxa-2-oxo-3-hydroxycycloheptane + NADP+ + H2O
-
no activity
-
-
?
2-hydroxycyclohexanone + NADPH + O2
1-oxa-2-oxo-3-hydroxycycloheptane + NADP+ + H2O
-
-
-
-
?
2-hydroxycyclohexanone + NADPH + O2
1-oxa-2-oxo-3-hydroxycycloheptane + NADP+ + H2O
-
no activity
-
-
?
2-methyl-cyclohexanone + NADPH + H+ + O2
1-oxa-2-oxo-3-methyl-cycloheptane + NADP+ + H2O
85% of the activity with cyclohexanone
-
-
?
2-methyl-cyclohexanone + NADPH + H+ + O2
1-oxa-2-oxo-3-methyl-cycloheptane + NADP+ + H2O
best substrate, 130% of the activity with cyclohexanone
-
-
?
2-methyl-cyclohexanone + NADPH + H+ + O2
1-oxa-2-oxo-3-methylcycloheptane + NADP+ + H2O
89% of the activity with cyclohexanone
-
-
?
2-methyl-cyclohexanone + NADPH + H+ + O2
1-oxa-2-oxo-3-methylcycloheptane + NADP+ + H2O
best substrate, 118% of the activity with cyclohexanone
-
-
?
2-methyl-cyclohexanone + NADPH + H+ + O2
1-oxa-2-oxo-3-methylcycloheptane + NADP+ + H2O
79.2% of the activity with cyclohexanone
-
-
?
2-methyl-cyclohexanone + NADPH + H+ + O2
1-oxa-2-oxo-3-methylcycloheptane + NADP+ + H2O
79.2% of the activity with cyclohexanone
-
-
?
2-methyl-cyclohexanone + NADPH + H+ + O2
1-oxa-2-oxo-3-methylcycloheptane + NADP+ + H2O
159% of the activity with cyclohexanone
-
-
?
2-methyl-cyclopentanone + NADPH + H+ + O2
1-oxa-2-oxo-3-methyl-cyclohexane + NADP+ + H2O
81% of the activity with cyclohexanone
-
-
?
2-methyl-cyclopentanone + NADPH + H+ + O2
1-oxa-2-oxo-3-methyl-cyclohexane + NADP+ + H2O
best substrate, 172% of the activity with cyclohexanone
-
-
?
2-methyl-cyclopentanone + NADPH + H+ + O2
1-oxa-2-oxo-3-methylcyclohexane + NADP+ + H2O
98% of the activity with cyclohexanone
-
-
?
2-methyl-cyclopentanone + NADPH + H+ + O2
1-oxa-2-oxo-3-methylcyclohexane + NADP+ + H2O
60.5% of the activity with cyclohexanone
-
-
?
2-methyl-cyclopentanone + NADPH + H+ + O2
1-oxa-2-oxo-3-methylcyclohexane + NADP+ + H2O
60.5% of the activity with cyclohexanone
-
-
?
2-methyl-cyclopentanone + NADPH + H+ + O2
1-oxa-2-oxo-3-methylcyclohexane + NADP+ + H2O
92% of the activity with cyclohexanone
-
-
?
2-methylcyclohexanone + NADPH + O2
1-oxa-2-oxo-3-methylcycloheptane + NADP+ + H2O
-
-
-
-
?
2-methylcyclohexanone + NADPH + O2
1-oxa-2-oxo-3-methylcycloheptane + NADP+ + H2O
-
-
-
-
?
2-methylcyclohexanone + NADPH + O2
1-oxa-2-oxo-3-methylcycloheptane + NADP+ + H2O
-
-
-
-
?
2-methylcyclohexanone + NADPH + O2
1-oxa-2-oxo-3-methylcycloheptane + NADP+ + H2O
-
-
-
-
?
2-methylcyclohexanone + NADPH + O2
1-oxa-2-oxo-3-methylcycloheptane + NADP+ + H2O
-
-
-
-
?
2-methylcyclohexanone + NADPH + O2
1-oxa-2-oxo-3-methylcycloheptane + NADP+ + H2O
-
-
-
-
?
2-phenylcyclohexanone + NADPH + H+ + O2
1-oxa-2-oxo-3-phenylcycloheptane + NADP+ + H2O
-
-
-
?
2-phenylcyclohexanone + NADPH + H+ + O2
1-oxa-2-oxo-3-phenylcycloheptane + NADP+ + H2O
11% of the activity with cyclohexanone
-
-
?
3,3,5-trimethyl-cyclohexanone + NADPH + H+ + O2
trimethyl-epsilon-caprolactone + NADP+ + H2O
-
-
-
?
3,3,5-trimethyl-cyclohexanone + NADPH + H+ + O2
trimethyl-epsilon-caprolactone + NADP+ + H2O
-
-
-
?
3,3,5-trimethylcyclohexanone + NADPH + O2 + H+
4,6,6-trimethyloxepan-2-one + 4,4,6-trimethyloxepan-2-one + NADP+ + H2O
90% conversion efficincy, purified enzyme
-
-
?
3,3,5-trimethylcyclohexanone + NADPH + O2 + H+
4,6,6-trimethyloxepan-2-one + 4,4,6-trimethyloxepan-2-one + NADP+ + H2O
-
-
91% conversion at 20 h, 1/1 isomer with 98% enantiomeric excess
-
?
4-ethylcyclohexanone + NADPH + O2 + H+
(5S)-5-ethyloxepan-2-one + NADP+ + H2O
95% conversion efficincy, purified enzyme
-
-
?
4-ethylcyclohexanone + NADPH + O2 + H+
(5S)-5-ethyloxepan-2-one + NADP+ + H2O
-
-
98% enantiomeric excess
-
?
4-hydroxy-cyclohexanone + NADPH + O2
4-hydroxy-hexano-6-lactone + NADP+ + H2O
-
-
-
-
?
4-hydroxy-cyclohexanone + NADPH + O2
4-hydroxy-hexano-6-lactone + NADP+ + H2O
-
an enantioselective Baeyer-Villiger oxidation
-
-
?
4-hydroxy-cyclohexanone + NADPH + O2
4-hydroxy-hexano-6-lactone + NADP+ + H2O
-
-
-
-
?
4-hydroxy-cyclohexanone + NADPH + O2
4-hydroxy-hexano-6-lactone + NADP+ + H2O
-
an enantioselective Baeyer-Villiger oxidation
-
-
?
4-hydroxy-cyclohexanone + NADPH + O2
4-hydroxy-hexano-6-lactone + NADP+ + H2O
-
low enantioselectivity
-
-
?
4-hydroxycyclohexanone + NADPH + O2
1-oxa-2-oxo-5-hydroxycycloheptane + NADP+ + H2O
-
-
-
-
?
4-hydroxycyclohexanone + NADPH + O2
1-oxa-2-oxo-5-hydroxycycloheptane + NADP+ + H2O
-
-
-
-
?
4-methoxythioanisole + NADPH + H+ + O2
1-(methanesulfinyl)-4-methoxybenzene + NADP+ + H2O
-
-
-
?
4-methoxythioanisole + NADPH + H+ + O2
1-(methanesulfinyl)-4-methoxybenzene + NADP+ + H2O
-
-
-
?
4-methylcyclohexanone + NADPH + O2
1-oxa-2-oxo-5-methylcycloheptane + NADP+ + H2O
-
-
-
-
?
4-methylcyclohexanone + NADPH + O2
1-oxa-2-oxo-5-methylcycloheptane + NADP+ + H2O
-
-
-
-
?
4-methylcyclohexanone + NADPH + O2
1-oxa-2-oxo-5-methylcycloheptane + NADP+ + H2O
-
-
-
-
?
4-methylcyclohexanone + NADPH + O2 + H+
(5S)-5-methyloxepan-2-one + NADP+ + H2O
70% conversion efficincy, purified enzyme
-
-
?
4-methylcyclohexanone + NADPH + O2 + H+
(5S)-5-methyloxepan-2-one + NADP+ + H2O
-
-
98% 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
-
-
enantiopure product
-
?
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
-
-
enantiopure product
-
?
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
(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
?
-
-
-
-
?
bicyclo[3.2.0]hept-2-en-6-one + NADPH + H+ + O2
?
the enzyme produces all four possible lactones
-
-
?
bicyclo[3.2.0]hept-2-en-6-one + NADPH + H+ + O2
?
the enzyme produces all four possible lactones
-
-
?
bicyclo[3.2.0]hept-2-en-6-one + NADPH + H+ + O2
?
the enzyme produces all four possible lactones
-
-
?
bicyclo[3.2.0]hept-2-en-6-one + NADPH + O2
?
-
racemic substrate
-
-
?
bicyclo[3.2.0]hept-2-en-6-one + NADPH + O2
?
-
recombinant from E. coli
-
-
?
bicyclo[3.2.0]hept-2-en-6-one + NADPH + O2
?
-
recombinant in E. coli
-
-
?
cyclobutanone + NADPH + H+ + O2
1-oxa-2-oxo-cyclopentane + NADP+ + H2O
4% of the activity with cyclohexanone
-
-
?
cyclobutanone + NADPH + H+ + O2
1-oxa-2-oxo-cyclopentane + NADP+ + H2O
92% of the activity with cyclohexanone
-
-
?
cyclobutanone + NADPH + H+ + O2
1-oxa-2-oxo-cyclopentane + NADP+ + H2O
86.9% of the activity with cyclohexanone
-
-
?
cyclobutanone + NADPH + H+ + O2
1-oxa-2-oxo-cyclopentane + NADP+ + H2O
86.9% of the activity with cyclohexanone
-
-
?
cyclobutanone + NADPH + H+ + O2
1-oxa-2-oxo-cyclopentane + NADP+ + H2O
3% of the activity with cyclohexanone
-
-
?
cyclobutanone + NADPH + H+ + O2
1-oxa-2-oxo-cyclopentane + NADP+ + H2O
4% of the activity with cyclohexanone
-
-
?
cyclobutanone + NADPH + O2
1-oxa-2-oxo-cyclopentane + NADP+ + H2O
-
-
-
-
?
cyclobutanone + NADPH + O2
1-oxa-2-oxo-cyclopentane + NADP+ + H2O
-
-
-
-
?
cyclobutanone + NADPH + O2
1-oxa-2-oxo-cyclopentane + NADP+ + H2O
-
-
-
-
?
cyclobutanone + NADPH + O2
1-oxa-2-oxo-cyclopentane + NADP+ + H2O
-
-
-
-
?
cyclobutanone + NADPH + O2
1-oxa-2-oxo-cyclopentane + NADP+ + H2O
-
-
-
-
?
cyclobutanone + NADPH + O2
1-oxa-2-oxo-cyclopentane + NADP+ + H2O
-
-
-
-
?
cyclodecanone + NADPH + H+ + O2
1-oxa-2-oxo-cycloundecane + NADP+ + H2O
4% of the activity with cyclohexanone
-
-
?
cyclodecanone + NADPH + H+ + O2
1-oxa-2-oxo-cycloundecane + NADP+ + H2O
5% of the activity with cyclohexanone
-
-
?
cyclodecanone + NADPH + H+ + O2
1-oxa-2-oxo-cycloundecane + NADP+ + H2O
2% of the activity with cyclohexanone
-
-
?
cyclodecanone + NADPH + H+ + O2
1-oxa-2-oxo-cycloundecane + NADP+ + H2O
6% of the activity with cyclohexanone
-
-
?
cycloheptanone + NADPH + H+ + O2
1-oxa-2-oxo-cyclooctane + NADP+ + H2O
108% of the activity with cyclohexanone
-
-
?
cycloheptanone + NADPH + H+ + O2
1-oxa-2-oxo-cyclooctane + NADP+ + H2O
80% of the activity with cyclohexanone
-
-
?
cycloheptanone + NADPH + H+ + O2
1-oxa-2-oxo-cyclooctane + NADP+ + H2O
23.5% of the activity with cyclohexanone
-
-
?
cycloheptanone + NADPH + H+ + O2
1-oxa-2-oxo-cyclooctane + NADP+ + H2O
23.5% of the activity with cyclohexanone
-
-
?
cycloheptanone + NADPH + H+ + O2
1-oxa-2-oxo-cyclooctane + NADP+ + H2O
166% of the activity with cyclohexanone
-
-
?
cycloheptanone + NADPH + H+ + O2
1-oxa-2-oxo-cyclooctane + NADP+ + H2O
73% of the activity with cyclohexanone
-
-
?
cycloheptanone + NADPH + H+ + O2
1-oxa-2-oxo-cyclooctane + NADP+ + H2O
90% of the activity with cyclohexanone
-
-
?
cycloheptanone + NADPH + O2
1-oxa-2-oxo-cyclooctane + NADP+ + H2O
-
-
-
-
?
cycloheptanone + NADPH + O2
1-oxa-2-oxo-cyclooctane + NADP+ + H2O
-
-
-
-
?
cycloheptanone + NADPH + O2
1-oxa-2-oxo-cyclooctane + NADP+ + H2O
-
-
-
-
?
cycloheptanone + NADPH + O2
1-oxa-2-oxo-cyclooctane + NADP+ + H2O
-
-
-
-
?
cycloheptanone + NADPH + O2
1-oxa-2-oxo-cyclooctane + NADP+ + H2O
-
-
-
-
?
cycloheptanone + NADPH + O2
1-oxa-2-oxo-cyclooctane + NADP+ + H2O
-
-
-
-
?
cyclohexan-1,2-dione + NADPH + O2
1-oxa-2,3-dioxo-cycloheptane + NADP+ + H2O
-
-
-
-
?
cyclohexan-1,2-dione + NADPH + O2
1-oxa-2,3-dioxo-cycloheptane + NADP+ + H2O
-
-
-
-
?
cyclohexan-1,2-dione + NADPH + O2
1-oxa-2,3-dioxo-cycloheptane + NADP+ + H2O
-
-
-
-
?
cyclohexan-1,4-dione + NADPH + O2
1-oxa-2,5-dioxo-cycloheptane + NADP+ + H2O
-
-
-
-
?
cyclohexan-1,4-dione + NADPH + O2
1-oxa-2,5-dioxo-cycloheptane + NADP+ + H2O
-
-
-
-
?
cyclohexanone + NADPH + H+ + O2
epsilon-caprolactone + NADP+ + H2O
-
-
-
-
?
cyclohexanone + NADPH + H+ + O2
epsilon-caprolactone + NADP+ + H2O
-
-
-
-
?
cyclohexanone + NADPH + H+ + O2
epsilon-caprolactone + NADP+ + H2O
-
-
-
?
cyclohexanone + NADPH + H+ + O2
epsilon-caprolactone + NADP+ + H2O
an asymmetric Baeyer-Villiger biooxidation, overview
-
-
?
cyclohexanone + NADPH + H+ + O2
epsilon-caprolactone + NADP+ + H2O
best substrate, an asymmetric Baeyer-Villiger biooxidation, overview
-
-
?
cyclohexanone + NADPH + H+ + O2
epsilon-caprolactone + NADP+ + H2O
-
-
-
?
cyclohexanone + NADPH + H+ + O2
epsilon-caprolactone + NADP+ + H2O
an asymmetric Baeyer-Villiger biooxidation, overview
-
-
?
cyclohexanone + NADPH + H+ + O2
epsilon-caprolactone + NADP+ + H2O
-
-
-
?
cyclohexanone + NADPH + H+ + O2
epsilon-caprolactone + NADP+ + H2O
best substrate, an asymmetric Baeyer-Villiger biooxidation, overview
-
-
?
cyclohexanone + NADPH + H+ + O2
epsilon-caprolactone + NADP+ + H2O
best substrate
-
-
?
cyclohexanone + NADPH + H+ + O2
epsilon-caprolactone + NADP+ + H2O
best substrate
-
-
?
cyclohexanone + NADPH + H+ + O2
epsilon-caprolactone + NADP+ + H2O
-
-
-
?
cyclohexanone + NADPH + H+ + O2
epsilon-caprolactone + NADP+ + H2O
an asymmetric Baeyer-Villiger biooxidation, overview
-
-
?
cyclohexanone + NADPH + H+ + O2
epsilon-caprolactone + NADP+ + H2O
best substrate, an asymmetric Baeyer-Villiger biooxidation, overview
-
-
?
cyclohexanone + NADPH + H+ + O2
epsilon-caprolactone + NADP+ + H2O
-
-
-
?
cyclohexanone + NADPH + H+ + O2
epsilon-caprolactone + NADP+ + H2O
an asymmetric Baeyer-Villiger biooxidation, overview
-
-
?
cyclohexanone + NADPH + H+ + O2
epsilon-caprolactone + NADP+ + H2O
-
-
-
?
cyclohexanone + NADPH + H+ + O2
epsilon-caprolactone + NADP+ + H2O
an asymmetric Baeyer-Villiger biooxidation, overview
-
-
?
cyclohexanone + NADPH + H+ + O2
epsilon-caprolactone + NADP+ + H2O
-
-
-
?
cyclohexanone + NADPH + H+ + O2
epsilon-caprolactone + NADP+ + H2O
best substrate, an asymmetric Baeyer-Villiger biooxidation, overview
-
-
?
cyclohexanone + NADPH + H+ + O2
hexano-6-lactone + NADP+ + H2O
100% conversion efficincy, purified enzyme
-
-
?
cyclohexanone + NADPH + H+ + O2
hexano-6-lactone + NADP+ + H2O
-
-
-
-
?
cyclohexanone + NADPH + H+ + O2
hexano-6-lactone + NADP+ + H2O
-
-
-
-
?
cyclohexanone + NADPH + H+ + O2
hexano-6-lactone + NADP+ + H2O
-
-
-
?
cyclohexanone + NADPH + H+ + O2
hexano-6-lactone + NADP+ + H2O
-
-
-
?
cyclohexanone + NADPH + H+ + O2
hexano-6-lactone + NADP+ + H2O
-
-
-
?
cyclohexanone + NADPH + H+ + O2
hexano-6-lactone + NADP+ + H2O
-
-
-
?
cyclohexanone + NADPH + H+ + O2
hexano-6-lactone + NADP+ + H2O
-
-
-
?
cyclohexanone + NADPH + O2
1-oxa-2-oxocycloheptane + NADP+ + H2O
-
-
-
-
?
cyclohexanone + NADPH + O2
1-oxa-2-oxocycloheptane + NADP+ + H2O
-
enzyme plays an important role in degradation of keto-compounds by microorganisms
-
-
?
cyclohexanone + NADPH + O2
1-oxa-2-oxocycloheptane + NADP+ + H2O
-
pathway
-
-
?
cyclohexanone + NADPH + O2
1-oxa-2-oxocycloheptane + NADP+ + H2O
-
pathway
-
-
?
cyclohexanone + NADPH + O2
1-oxa-2-oxocycloheptane + NADP+ + H2O
-
depending on inducing growth substrate
-
-
?
cyclohexanone + NADPH + O2
1-oxa-2-oxocycloheptane + NADP+ + H2O
-
depending on inducing growth substrate
-
-
?
cyclohexanone + NADPH + O2
6-hexanolide + NADP+ + H2O
-
-
product: epsilon-caprolactone i.e. 1-oxa-2-oxocycloheptane
?
cyclohexanone + NADPH + O2
6-hexanolide + NADP+ + H2O
-
-
-
-
?
cyclohexanone + NADPH + O2
6-hexanolide + NADP+ + H2O
-
-
product: epsilon-caprolactone i.e. 1-oxa-2-oxocycloheptane
?
cyclohexanone + NADPH + O2
6-hexanolide + NADP+ + H2O
-
-
product: epsilon-caprolactone i.e. 1-oxa-2-oxocycloheptane
?
cyclohexanone + NADPH + O2
6-hexanolide + NADP+ + H2O
-
-
product: epsilon-caprolactone i.e. 1-oxa-2-oxocycloheptane
?
cyclohexanone + NADPH + O2
6-hexanolide + NADP+ + H2O
-
product: epsilon-caprolactone i.e. 1-oxa-2-oxocycloheptane
?
cyclohexanone + NADPH + O2
6-hexanolide + NADP+ + H2O
-
activity limited to cyclic ketones
product: epsilon-caprolactone i.e. 1-oxa-2-oxocycloheptane
?
cyclohexanone + NADPH + O2
6-hexanolide + NADP+ + H2O
-
-
product: epsilon-caprolactone i.e. 1-oxa-2-oxocycloheptane
?
cyclohexanone + NADPH + O2
6-hexanolide + NADP+ + H2O
-
-
product: epsilon-caprolactone i.e. 1-oxa-2-oxocycloheptane
?
cyclohexanone + NADPH + O2
6-hexanolide + NADP+ + H2O
-
-
product: epsilon-caprolactone i.e. 1-oxa-2-oxocycloheptane
?
cyclohexanone + NADPH + O2
6-hexanolide + NADP+ + H2O
-
-
product: epsilon-caprolactone i.e. 1-oxa-2-oxocycloheptane
?
cyclohexanone + NADPH + O2
6-hexanolide + NADP+ + H2O
-
-
product: epsilon-caprolactone i.e. 1-oxa-2-oxocycloheptane
?
cyclohexanone + NADPH + O2
epsilon-caprolactone + NADP+ + H2O
-
-
-
-
?
cyclohexanone + NADPH + O2
epsilon-caprolactone + NADP+ + H2O
-
-
-
-
?
cyclohexanone + NADPH + O2
epsilon-caprolactone + NADP+ + H2O
initial step of the degradation of cyclohexanone to adipic acid
-
-
?
cyclohexanone + NADPH + O2
epsilon-caprolactone + NADP+ + H2O
initial step of the degradation of cyclohexanone to adipic acid
-
-
?
cyclohexanone + NADPH + O2
hexano-6-lactone + NADP+ + H2O
-
-
-
-
?
cyclohexanone + NADPH + O2
hexano-6-lactone + NADP+ + H2O
-
-
-
-
?
cyclohexanone + NADPH + O2
hexano-6-lactone + NADP+ + H2O
-
-
-
-
?
cyclohexanone + NADPH + O2
hexano-6-lactone + NADP+ + H2O
-
-
-
?
cyclohexanone + NADPH + O2
hexano-6-lactone + NADP+ + H2O
-
-
-
-
?
cyclohexanone + NADPH + O2
hexano-6-lactone + NADP+ + H2O
-
-
-
-
?
cyclohexanone + NADPH + O2
hexano-6-lactone + NADP+ + H2O
-
-
-
?
cyclooctanone + NADPH + H+ + O2
1-oxa-2-oxo-cyclononane + NADP+ + H2O
18% of the activity with cyclohexanone
-
-
?
cyclooctanone + NADPH + H+ + O2
1-oxa-2-oxo-cyclononane + NADP+ + H2O
42% of the activity with cyclohexanone
-
-
?
cyclooctanone + NADPH + H+ + O2
1-oxa-2-oxo-cyclononane + NADP+ + H2O
3.1% of the activity with cyclohexanone
-
-
?
cyclooctanone + NADPH + H+ + O2
1-oxa-2-oxo-cyclononane + NADP+ + H2O
17% of the activity with cyclohexanone
-
-
?
cyclooctanone + NADPH + H+ + O2
1-oxa-2-oxo-cyclononane + NADP+ + H2O
23% of the activity with cyclohexanone
-
-
?
cyclooctanone + NADPH + H+ + O2
1-oxa-2-oxo-cyclononane + NADP+ + H2O
4% of the activity with cyclohexanone
-
-
?
cyclooctanone + NADPH + O2
1-oxa-2-oxo-cyclononane + NADP+ + H2O
-
-
-
-
?
cyclooctanone + NADPH + O2
1-oxa-2-oxo-cyclononane + NADP+ + H2O
-
-
-
-
?
cyclooctanone + NADPH + O2
1-oxa-2-oxo-cyclononane + NADP+ + H2O
-
-
-
-
?
cyclooctanone + NADPH + O2
1-oxa-2-oxo-cyclononane + NADP+ + H2O
-
-
-
-
?
cyclooctanone + NADPH + O2
1-oxa-2-oxo-cyclononane + NADP+ + H2O
-
-
-
-
?
cyclooctanone + NADPH + O2
1-oxa-2-oxo-cyclononane + NADP+ + H2O
-
-
-
-
?
cyclooctanone + NADPH + O2
1-oxa-2-oxo-cyclononane + NADP+ + H2O
-
low activity
-
-
?
cyclopentanone + NADPH + H+ + O2
1-oxa-2-oxo-cyclohexane + NADP+ + H2O
100% conversion efficincy, purified enzyme
-
-
?
cyclopentanone + NADPH + H+ + O2
1-oxa-2-oxo-cyclohexane + NADP+ + H2O
42% of the activity with cyclohexanone
-
-
?
cyclopentanone + NADPH + H+ + O2
1-oxa-2-oxo-cyclohexane + NADP+ + H2O
95% of the activity with cyclohexanone
-
-
?
cyclopentanone + NADPH + H+ + O2
1-oxa-2-oxo-cyclohexane + NADP+ + H2O
11.3% of the activity with cyclohexanone
-
-
?
cyclopentanone + NADPH + H+ + O2
1-oxa-2-oxo-cyclohexane + NADP+ + H2O
37% of the activity with cyclohexanone
-
-
?
cyclopentanone + NADPH + H+ + O2
1-oxa-2-oxo-cyclohexane + NADP+ + H2O
48% of the activity with cyclohexanone
-
-
?
cyclopentanone + NADPH + H+ + O2
1-oxa-2-oxo-cyclohexane + NADP+ + H2O
65% of the activity with cyclohexanone
-
-
?
cyclopentanone + NADPH + O2
1-oxa-2-oxo-cyclohexane + NADP+ + H2O
-
-
-
-
?
cyclopentanone + NADPH + O2
1-oxa-2-oxo-cyclohexane + NADP+ + H2O
-
-
-
-
?
cyclopentanone + NADPH + O2
1-oxa-2-oxo-cyclohexane + NADP+ + H2O
-
-
-
-
?
cyclopentanone + NADPH + O2
1-oxa-2-oxo-cyclohexane + NADP+ + H2O
-
-
-
-
?
cyclopentanone + NADPH + O2
1-oxa-2-oxo-cyclohexane + NADP+ + H2O
-
-
-
-
?
cyclopentanone + NADPH + O2
1-oxa-2-oxo-cyclohexane + NADP+ + H2O
-
-
-
-
?
ethyl p-tolyl sulfide + NADPH + O2
(S)-ethyl p-tolyl sulfoxide + NADP+ + H2O
-
-
-
-
?
ethyl p-tolyl sulfide + NADPH + O2
(S)-ethyl p-tolyl sulfoxide + NADP+ + H2O
-
-
-
?
methyl phenyl sulfide + NADPH + H+ + O2
(R)-methyl phenyl sulfoxide + NADP+ + H2O
-
recombinant from E. coli
-
?
methyl phenyl sulfide + NADPH + H+ + O2
(R)-methyl phenyl sulfoxide + NADP+ + H2O
-
recombinant in E. coli
-
-
?
methyl phenyl sulfide + NADPH + H+ + O2
(R)-methyl phenyl sulfoxide + NADP+ + H2O
-
-
-
-
?
methyl phenyl sulfide + NADPH + H+ + O2
(R)-methyl phenyl sulfoxide + NADP+ + H2O
-
recombinant enzyme in E. coli or Saccharomyces cerevisiae
-
-
?
N-methylbenzylamine + NADPH + O2
N-benzyl-N-methylhydroxylamine + NADP+ + H2O
-
-
-
-
?
N-methylbenzylamine + NADPH + O2
N-benzyl-N-methylhydroxylamine + NADP+ + H2O
-
-
-
-
?
tert-butyl methyl sulfide + NADPH + O2
?
-
recombinant enzyme in E. coli or Saccharomyces cerevisiae
-
-
?
additional information
?
-
-
inductive growth on cyclohexanol, addition of cyclohexanone
-
-
?
additional information
?
-
-
also catalyze the oxidation of several more secondary amines
-
-
?
additional information
?
-
-
can catalyze the asymmetric sulfoxidation of numerous alkyl aryl sulfides, dialkyl sulfides, 1,3-dithioacetals, organic cyclic sulfites, and the oxidation alkyl aryl amines
-
-
?
additional information
?
-
-
BaeyerVilliger oxidation of racemic bicyclic diketones such as the WielandMiescher and the HajosParrish diketones and of some of their derivatives to the correspondent lactones in a highly regio- and enantioselective manner, overview
-
-
?
additional information
?
-
-
the enzyme catalyses the NADPH-dependent enantioselective oxidation of ketones and of several heteroatoms such as nitrogen, sulfur, phosphorous and selenium present in organic compounds
-
-
?
additional information
?
-
-
BaeyerVilliger oxidation of racemic bicyclic diketones such as the WielandMiescher and the HajosParrish diketones and of some of their derivatives to the correspondent lactones in a highly regio- and enantioselective manner, overview
-
-
?
additional information
?
-
-
also catalyze the oxidation of several more secondary amines
-
-
?
additional information
?
-
-
can catalyze the asymmetric sulfoxidation of numerous alkyl aryl sulfides, dialkyl sulfides, 1,3-dithioacetals, organic cyclic sulfites, and the oxidation alkyl aryl amines
-
-
?
additional information
?
-
-
absolutely specific for NADPH as electron donor
-
-
?
additional information
?
-
-
active with diverse alkyl aryl sulfides, dialkyl sulfides and dialkyldisulfides
-
-
?
additional information
?
-
-
high enantioselectivity in oxidation of sulfides
-
-
?
additional information
?
-
-
high enantioselectivity in oxidation of sulfides
-
-
?
additional information
?
-
-
high enantioselectivity in oxidation of sulfides
-
-
?
additional information
?
-
-
active with benzyl alkyl sulfides with alkyl groups from methyl to hexyl and para-alkylbenzyl groups from methyl to butyl
-
-
?
additional information
?
-
-
oxidation of propargylic and allylic selenides
-
-
?
additional information
?
-
-
ability to convert aryl and alkyl boronic acids into phenols and alcohols, racemic 2-methylcyclohexyl boronic acid is processed to 2-methylcyclohexanol
-
-
?
additional information
?
-
-
production of optically pure sulfoxides by biotransformation in whole cell systems of several sulfides, dithianes and dithiolanes
-
-
?
additional information
?
-
-
substrate specificity and enantioselectivity of wild-type and mutant enzymes, overview
-
-
?
additional information
?
-
-
substrate specificity and enantioselectivity of wild-type and mutant enzymes, overview
-
-
?
additional information
?
-
also oxidizes a large variety of cyclic and linear ketones
-
-
?
additional information
?
-
substrate specificity of the recombinant His-tagged enzyme, overview
-
-
?
additional information
?
-
substrate specificity of the recombinant His-tagged enzyme, overview
-
-
?
additional information
?
-
also oxidizes a large variety of cyclic and linear ketones
-
-
?
additional information
?
-
substrate specificity of the recombinant His-tagged enzyme, overview
-
-
?
additional information
?
-
-
substrate specificity and enantioselectivity, overview, the enzyme catalyzes the Baeyer-Villiger oxidations of prochiral 4-substituted ketones, e.g. 4,4-disubstituted cyclohexanones, to the corresponding lactones, configuration of lactone products, 4-tert-butylcyclohexanone is a poor substrate for wild-type and mutant enzymes, no activity with 4-hydroxy-4-phenylcyclohexanone of wild-type enzyme and mutant F432S, 4-tert-butylcyclohexanone is a poor substrate
-
-
?
additional information
?
-
enzyme shows excellent stereodiscrimination of 2-substituted cyclic ketones. The expression system exhibits no activity with ethene or cis-1,2-dichloroethene as substrates under the tested conditions
-
-
?
additional information
?
-
-
no activity towards straight-chain alkanones
-
-
?
additional information
?
-
-
also oxidizes a large variety of cyclic and linear ketones
-
-
?
additional information
?
-
-
also oxidizes a large variety of cyclic and linear ketones
-
-
?
additional information
?
-
also oxidizes a large variety of cyclic and linear ketones
-
-
?
additional information
?
-
also oxidizes a large variety of cyclic and linear ketones
-
-
?
additional information
?
-
no activity with 1,3-cyclohexandione
-
-
?
additional information
?
-
no activity with 1,2-cyclohexandione
-
-
?
additional information
?
-
-
no activity towards straight-chain alkanones
-
-
?
additional information
?
-
-
no activity towards straight-chain alkanones
-
-
?
additional information
?
-
-
absolutely specific for NADPH as electron donor
-
-
?
