1.14.13.16: cyclopentanone monooxygenase
This is an abbreviated version!
For detailed information about cyclopentanone monooxygenase, go to the full flat file.
Word Map on EC 1.14.13.16
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1.14.13.16
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baeyer-villiger
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biooxidation
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lactones
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polyelectrolyte
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encapsulated
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enantioselective
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capsules
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flavin
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cyclohexanone
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cellulose
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synthesis
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alginate
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enantiomeric
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regioisomeric
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conversions
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propidium
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immobilised
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polyvinyl
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autofluorescence
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biocatalysis
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ketone
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ncimb
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iodide
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regio
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halved
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drug development
- 1.14.13.16
-
baeyer-villiger
-
biooxidation
- lactones
-
polyelectrolyte
-
encapsulated
-
enantioselective
- capsules
- flavin
- cyclohexanone
- cellulose
- synthesis
- alginate
-
enantiomeric
-
regioisomeric
-
conversions
- propidium
-
immobilised
-
polyvinyl
-
autofluorescence
-
biocatalysis
- ketone
-
ncimb
- iodide
-
regio
-
halved
- drug development
Reaction
Synonyms
CPMO, CpnB, cyclopentanone monooxygenase, cyclopentanone oxygenase, More
ECTree
1.14.13.16 cyclopentanone monooxygenaseAdvanced search results
results (
results (Substrates Products
Substrates Products on EC 1.14.13.16 - cyclopentanone 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
(1R,5S)-8-oxabicyclo[3.2.1]oct-6-en-3-one + NADPH + O2
(1S,6S)-3,9-dioxabicyclo[4.2.1]non-7-en-4-one + NADP+ + H2O
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stereospecific (1S,6S)-product formation
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?
2-methylcyclohexanone + NADPH + O2
1-oxa-2-oxo-3-methylcycloheptane + NADP+ + H2O
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-
-
-
?
2-phenylcyclohexanone + NADPH + H+ + O2
? + NADP+ + H2O
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high activity with PAMO enzyme mutant P253F/G254A/R258M/L443F, almost no activity with wild-type PAMO (EC 1.14.13.92)
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-
?
4-acetoxycyclohexanone + NADPH + H+ + O2
5-acetoxyoxepan-2-one + NADP+ + H2O
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-
-
-
?
4-allyloxycyclohexanone + NADPH + H+ + O2
5-allyloxyoxepan-2-one + NADP+ + H2O
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-
-
-
?
4-benzyloxycyclohexanone + NADPH + H+ + O2
5-benzyloxyoxepan-2-one + NADP+ + H2O
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-
-
-
?
4-chlorocyclohexanone + NADPH + H+ + O2
5-chlorooxepan-2-one + NADP+ + H2O
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-
-
-
?
4-ethoxy-cyclohexanone + NADPH + O2
4-ethoxy-hexano-6-lactone + NADP+ + H2O
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-
-
-
?
4-ethoxycyclohexanone + NADPH + H+ + O2
5-ethoxyoxepane-2-one + NADP+ + H2O
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-
-
-
?
4-ethyl-cyclohexanone + NADPH + O2
4-ethyl-hexano-6-lactone + NADP+ + H2O
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-
-
-
?
4-methoxy-cyclohexanone + NADPH + O2
4-methoxy-hexano-6-lactone + NADP+ + H2O
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-
-
-
?
4-n-propyl-cyclohexanone + NADPH + O2
4-n-propyl-hexano-6-lactone + NADP+ + H2O
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-
-
-
?
cycloheptanone + NADPH + O2
1-oxa-2-oxocyclooctane + NADP+ + H2O
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poor substrate
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-
?
cyclohexanone + NADPH + O2
1-oxa-2-oxocycloheptane + NADP+ + H2O
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-
-
-
?
cyclooctanone + NADPH + O2
1-oxa-2-oxocyclononane + NADP+ + H2O
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poor substrate
-
-
?
4-acetoxy-cyclohexanone + NADPH + O2
4-acetoxy-hexano-6-lactone + NADP+ + H2O
-
-
-
-
?
4-acetoxy-cyclohexanone + NADPH + O2
4-acetoxy-hexano-6-lactone + NADP+ + H2O
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low enantioselectivity
-
-
?
4-acetoxy-cyclohexanone + NADPH + O2
4-acetoxy-hexano-6-lactone + NADP+ + H2O
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low enantioselectivity
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-
?
4-acetoxy-cyclohexanone + NADPH + O2
4-acetoxy-hexano-6-lactone + NADP+ + H2O
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-
-
-
?
4-allyl-cyclohexanone + NADPH + O2
4-allyl-hexano-6-lactone + NADP+ + H2O
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-
-
-
?
4-allyl-cyclohexanone + NADPH + O2
4-allyl-hexano-6-lactone + NADP+ + H2O
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-
-
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?
4-hydroxy-cyclohexanone + NADPH + O2
4-hydroxy-hexano-6-lactone + NADP+ + H2O
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-
-
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?
4-hydroxy-cyclohexanone + NADPH + O2
4-hydroxy-hexano-6-lactone + NADP+ + H2O
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high enantioselectivity with 85% formation of the S-isomer, Ser450 is responsible for the high stereoselectivity
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-
?
4-hydroxy-cyclohexanone + NADPH + O2
4-hydroxy-hexano-6-lactone + NADP+ + H2O
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high enantioselectivity with 85% formation of the S-isomer, Ser450 is responsible for the high stereoselectivity
-
-
?
4-hydroxy-cyclohexanone + NADPH + O2
4-hydroxy-hexano-6-lactone + NADP+ + H2O
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-
-
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?
4-methyl-cyclohexanone + NADPH + O2
4-methyl-hexano-6-lactone + NADP+ + H2O
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-
-
-
?
4-methyl-cyclohexanone + NADPH + O2
4-methyl-hexano-6-lactone + NADP+ + H2O
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low enantioselectivity
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-
?
4-methyl-cyclohexanone + NADPH + O2
4-methyl-hexano-6-lactone + NADP+ + H2O
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low enantioselectivity
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-
?
4-methyl-cyclohexanone + NADPH + O2
4-methyl-hexano-6-lactone + NADP+ + H2O
-
-
-
?
cyclopentanone + NADPH + H+ + O2
5-valerolactone + NADP+ + H2O
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high activity with PAMO enzyme mutant P253F/G254A/R258M/L443F, almost no activity with wild-type PAMO (EC 1.14.13.92)
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-
?
cyclopentanone + NADPH + O2
5-valerolactone + NADP+ + H2O
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-
-
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?
cyclopentanone + NADPH + O2
5-valerolactone + NADP+ + H2O
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-
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?
cyclopentanone + NADPH + O2
5-valerolactone + NADP+ + H2O
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-
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?
additional information
?
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the enzyme acts as Baeyer-Villiger monooxygenase, substrate specificity and enantioselectivity of wild-type and mutant enzymes, structure-function analysis and comparison to cyclohexanone monooxygenase, EC 1.14.13.22, residues Phe450 and Phe156 are important, overview
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?
additional information
?
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the enzyme acts as Baeyer-Villiger monooxygenase, substrate specificity and enantioselectivity, overview, 4-tert-butylcyclohexanone is a no substrate
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?
additional information
?
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the enzyme acts as Baeyer-Villiger monooxygenase, substrate specificity and enantioselectivity, overview, 4-tert-butylcyclohexanone is a no substrate
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-
?
additional information
?
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the enzyme acts as Baeyer-Villiger monooxygenase, substrate specificity and enantioselectivity of wild-type and mutant enzymes, structure-function analysis and comparison to cyclohexanone monooxygenase, EC 1.14.13.22, residues Phe450 and Phe156 are important, overview
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-
?
additional information
?
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the engineered phenylacetone monooxygenase (EC 1.14.13.92) enzyme mutant P253F/G254A/R258M/L443F has almost lost its activity with phenylacetone, but shows higher activity with cyclopentanone instead. Substrate binding analysis, overview
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