| Entry |
|
|---|
| 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 O2 as oxidant and incorporation or
reduction of oxygen. The oxygen incorporated need not be derived
from O2;
With NADH or NADPH as one donor, and incorporation of one atom of
oxygen into the other donor
 |
|---|
| 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
 |
|---|
| 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] |
|---|
| Cofactor |
FAD [CPD:C00016] |
|---|
| 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]. |
|---|
| Pathway |
PATH: ec00930 Caprolactam degradation |
|---|
| Orthology |
KO: K03379 cyclohexanone monooxygenase |
|---|
| Genes |
PIC: PICST_52278(FMO3) PICST_57936(FMO5)
MGR: MGG_06577
UMA: UM03415.1
PMY: Pmen_2620
ACI: ACIAD2339 ACIAD3192
MAQ: Maqu_3819 Maqu_3830
REU: Reut_B4935
REH: H16_B1746
BUR: Bcep18194_B1145 Bcep18194_B1220 Bcep18194_B2444 Bcep18194_B2514
Bcep18194_C6774 Bcep18194_C6776 Bcep18194_C7122 Bcep18194_C7142
BXE: Bxe_A3588 Bxe_C0276
AJS: Ajs_2102
MPT: Mpe_A2915 Mpe_B0579 Mpe_B0607
SCL: sce4944
PUB: SAR11_0845(smo)
PLA: Plav_0813 Plav_1165
BJA: blr2938 blr3857 blr6984
NAR: Saro_0510 Saro_1480 Saro_2452
MRA: MRA_1402
MBO: Mb1428c
MBB: BCG_1454c
MAV: MAV_1604 MAV_2805 MAV_3018 MAV_3029 MAV_3378 MAV_5119 MAV_5206
MSM: MSMEG_2567 MSMEG_5625
MUL: MUL_1053 MUL_1793 MUL_4813
MVA: Mvan_0615 Mvan_2013 Mvan_2243 Mvan_2671 Mvan_2894 Mvan_3104
Mvan_4961
MGI: Mflv_1789 Mflv_3736 Mflv_4103 Mflv_4332 Mflv_4506 Mflv_4607
MMC: Mmcs_0511 Mmcs_2024 Mmcs_2374 Mmcs_3189 Mmcs_4405
MKM: Mkms_0522 Mkms_2070 Mkms_2421 Mkms_3251 Mkms_4492
MJL: Mjls_0301 Mjls_0311 Mjls_0500 Mjls_2007 Mjls_2415 Mjls_4786
RHA: RHA1_ro01874 RHA1_ro02492 RHA1_ro03063 RHA1_ro03247
RHA1_ro03437 RHA1_ro06008 RHA1_ro06679 RHA1_ro06698
RHA1_ro08137 RHA1_ro09035 RHA1_ro09039 RHA1_ro10187
FAL: FRAAL3387
SEN: SACE_2596
 |
|---|
| Structures |
PDB: 3GWD 3GWF |
|---|
Reference
Authors
Title
Journal
Organism
|
1 [PMID:1261545]
Donoghue NA, Norris DB, Trudgill PW.
The purification and properties of cyclohexanone oxygenase from
Nocardia globerula CL1 and Acinetobacter NCIB 9871.
Eur. J. Biochem. 63 (1976) 175-92.
Acinetobacter sp., Norcardia globerula |
|---|
Reference
Authors
Title
Journal
Organism
|
2 [PMID:11551214]
Sheng D, Ballou DP, Massey V.
Mechanistic studies of cyclohexanone monooxygenase: chemical
properties of intermediates involved in catalysis.
Biochemistry. 40 (2001) 11156-67.
Acinetobacter sp., Norcardia globerula |
|---|
Reference
Authors
Title
Journal
|
3
Stewart, J.D.
Cyclohexanone monooxygenase: a useful reagent for asymmetric
Baeyer-Villiger reactions.
Curr. Org. Chem. 2 (1998) 195-216. |
|---|
Reference
Authors
Title
Journal
|
4
Chen, G., Kayser, M.M., Milhovilovic, M.D., Mrstik, M.E., Martinez,
C.A. and Stewart, J.D.
Asymmetric oxidations at sulfur catalyzed by engineered strains that
overexpress cyclohexanone monooxygenase.
New J. Chem. 23 (1999) 827-832. |
|---|
Reference
Authors
Title
Journal
|
5
Ottolina, G., Bianchi, S., Belloni, B., Carrea, G. and Danieli, B.
First asymmetric oxidation of tertiary amines by cyclohexanone
monooxygenase.
Tetrahedron Lett. 40 (1999) 8483-8486. |
|---|
Reference
Authors
Title
Journal
|
6
Colonna, S., Gaggero, N., Carrea, G., Ottolina, G., Pasta, P. and
Zambianchi, F.
First asymmetric epoxidation catalysed by cyclohexanone
monooxygenase.
Tetrahedron Lett. 43 (2002) 1797-1799. |
|---|
| Other DBs |
ExplorEnz - The Enzyme Database: 1.14.13.22
IUBMB Enzyme Nomenclature: 1.14.13.22
ExPASy - ENZYME nomenclature database: 1.14.13.22
UM-BBD (Biocatalysis/Biodegradation Database): 1.14.13.22
BRENDA, the Enzyme Database: 1.14.13.22
CAS: 52037-90-8 |
|---|
