KEGG   ENZYME: 1.14.13.22Help
Entry
EC 1.14.13.22               Enzyme                                 

Name
cyclohexanone monooxygenase;
cyclohexanone 1,2-monooxygenase;
cyclohexanone oxygenase;
cyclohexanone:NADPH:oxygen oxidoreductase (6-hydroxylating, 1,2-lactonizing)
Class
Oxidoreductases;
Acting on paired donors, with incorporation or reduction of molecular oxygen;
With NADH or NADPH as one donor, and incorporation of one atom of oxygen into the other donor
BRITE hierarchy
Sysname
cyclohexanone,NADPH:oxygen oxidoreductase (lactone-forming)
Reaction(IUBMB)
cyclohexanone + NADPH + H+ + O2 = hexano-6-lactone + NADP+ + H2O [RN:R02231]
Reaction(KEGG)
R02231;
(other) R06622
Show
Substrate
cyclohexanone [CPD:C00414];
NADPH [CPD:C00005];
H+ [CPD:C00080];
O2 [CPD:C00007]
Product
hexano-6-lactone [CPD:C01880];
NADP+ [CPD:C00006];
H2O [CPD:C00001]
Comment
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].
History
EC 1.14.13.22 created 1984, modified 2004
Pathway
Caprolactam degradation
Microbial metabolism in diverse environments
Orthology
K03379  
cyclohexanone monooxygenase
Genes
PIC: 
MGR: 
NHE: 
MAJ: 
CMT: 
MBE: 
AFM: 
AOR: 
AOR_1_1264054(AO090011000747) AOR_1_558054(AO090011000330)
ANG: 
ANI_1_1806104(An12g05000)
AFV: 
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NFI: 
PCS: 
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MIE: 
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MYO: 
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MMM: 
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FRE: 
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 » show all
Taxonomy
Reference
1  [PMID:1261545]
  Authors
Donoghue NA, Norris DB, Trudgill PW.
  Title
The purification and properties of cyclohexanone oxygenase from Nocardia globerula CL1 and Acinetobacter NCIB 9871.
  Journal
Eur. J. Biochem. 63 (1976) 175-92.
Reference
2  [PMID:11551214]
  Authors
Sheng D, Ballou DP, Massey V.
  Title
Mechanistic studies of cyclohexanone monooxygenase: chemical properties of intermediates involved in catalysis.
  Journal
Biochemistry. 40 (2001) 11156-67.
Reference
3
  Authors
Stewart, J.D.
  Title
Cyclohexanone monooxygenase: a useful reagent for asymmetric Baeyer-Villiger reactions.
  Journal
Curr. Org. Chem. 2 (1998) 195-216.
Reference
4
  Authors
Chen, G., Kayser, M.M., Milhovilovic, M.D., Mrstik, M.E., Martinez, C.A. and Stewart, J.D.
  Title
Asymmetric oxidations at sulfur catalyzed by engineered strains that overexpress cyclohexanone monooxygenase.
  Journal
New J. Chem. 23 (1999) 827-832.
Reference
5
  Authors
Ottolina, G., Bianchi, S., Belloni, B., Carrea, G. and Danieli, B.
  Title
First asymmetric oxidation of tertiary amines by cyclohexanone monooxygenase.
  Journal
Tetrahedron Lett. 40 (1999) 8483-8486.
Reference
6
  Authors
Colonna, S., Gaggero, N., Carrea, G., Ottolina, G., Pasta, P. and Zambianchi, F.
  Title
First asymmetric epoxidation catalysed by cyclohexanone monooxygenase.
  Journal
Tetrahedron Lett. 43 (2002) 1797-1799.
Other DBs
ExplorEnz - The Enzyme Database: 
IUBMB Enzyme Nomenclature: 
ExPASy - ENZYME nomenclature database: 
UM-BBD (Biocatalysis/Biodegradation Database): 
BRENDA, the Enzyme Database: 
CAS: 
52037-90-8

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