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 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)
Substrate
Product
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
ec01120 Microbial metabolism in diverse environments
Orthology
K03379 cyclohexanone monooxygenase
Genes
NHE : NECHADRAFT_48101 NECHADRAFT_54743 NECHADRAFT_82172
TATV : 25775502(TrAtP1_002380) 25776279(TrAtP1_010515) 25778655(TrAtP1_005079) 25779180(TrAtP1_008135) 25780666(TrAtP1_007204) 25785137(TrAtP1_009393) 25786157(TrAtP1_013292)
TASP : 36607502(TrAFT101_000279) 36608619(TrAFT101_004811) 36610081(TrAFT101_003230) 36614433(TrAFT101_004470) 36615451(TrAFT101_010711) 36618422(TrAFT101_011925)
NFI : NFIA_041810 NFIA_084900
AOR : AO090011000330 AO090011000747
AFV : AFLA_007728 AFLA_008145
APUU : APUU_22001S APUU_51614S APUU_61080S APUU_80445A APUU_80806S
PCS : N7525_000103 N7525_010738
CBET : CB0940_00783 CB0940_05932
CCAC : CcaHIS019_0106420(CcaverHIS019_0106420)
KIM : G3T16_06295 G3T16_16875
SNAP : PQ455_08140 PQ455_18135
SPZR : G5C33_14315 G5C33_18305
MAVU : RE97_00845 RE97_01270
MCHI : AN480_25660 AN480_26135
MMAL : CKJ54_23545 CKJ54_24035
MMAN : MMAN_37520 MMAN_38540
MSER : MTY59_09370 MTY59_12810 MTY59_13830
MSA : Mycsm_02390 Mycsm_05176 Mycsm_05379
MMAE : MMARE11_02790 MMARE11_03660
MLI : MULP_00286 MULP_00391
MPSE : MPSD_03990 MPSD_05030
MSHO : MSHO_13500 MSHO_17780
MKN : MKAN_15785 MKAN_18075
MYV : G155_06310 G155_12075
MYE : AB431_17350 AB431_22905
MDX : BTO20_22765 BTO20_29395
MSHG : MSG_00233 MSG_00343
MFJ : MFLOJ_28280 MFLOJ_31730 MFLOJ_32760
MSTO : MSTO_32130 MSTO_35750 MSTO_37030
MSIM : MSIM_21360 MSIM_22330
MSAK : MSAS_36170 MSAS_41630
MKU : I2456_01715 I2456_03905
MLW : MJO58_01365 MJO58_01855 MJO58_03520
MPAG : C0J29_01755 C0J29_04175
MNM : MNVM_17090 MNVM_25580
MGOR : H0P51_01600 H0P51_22560
MCOO : MCOO_20200 MCOO_33860
MBAI : MB901379_00225(ptlE_1) MB901379_00313(hapE_2)
MSEO : MSEO_41360 MSEO_42390 MSEO_45730
MGAU : MGALJ_07170 MGALJ_34870
MBRD : MBRA_13790 MBRA_14670 MBRA_50180 MBRA_55600
MPAA : MKK62_01585 MKK62_23385 MKK62_23910 MKK62_25455
MWU : PT015_08160 PT015_18635 PT015_19125
MSM : MSMEG_2567 MSMEG_5625
MSG : MSMEI_2507 MSMEI_5475
MSB : LJ00_12775 LJ00_27815
MSN : LI99_12775 LI99_27820
MSH : LI98_12780 LI98_27825
MSP : Mspyr1_11730 Mspyr1_34460
MCB : Mycch_1987 Mycch_4342
MFT : XA26_12580 XA26_24790
MPHL : MPHLCCUG_02191(hapE_4)
MRH : MycrhN_2714 MycrhN_5746
MTHN : 4412656_01660(hapE_6) 4412656_03830(pamO_4)
MHAS : MHAS_02515 MHAS_03439(penE)
MDU : MDUV_11450 MDUV_22700 MDUV_52170
MCHT : MCHIJ_09730 MCHIJ_10150
MAUU : NCTC10437_02096(hapE_7) NCTC10437_04678(pamO_7)
MMOR : MMOR_15380 MMOR_41870
MAIC : MAIC_30420 MAIC_41250
MALV : MALV_14370 MALV_45430
MARZ : MARA_18060 MARA_24920
MGAD : MGAD_16890 MGAD_34050
MHEV : MHEL_07900 MHEL_54040
MPOF : MPOR_25710 MPOR_50810
MMUC : C1S78_011425 C1S78_018235
MMAT : MMAGJ_10310 MMAGJ_55580
MBOK : MBOE_23300 MBOE_50050
MFG : K6L26_07215 K6L26_20150
MSEI : MSEDJ_26870 MSEDJ_28550
MFLV : NCTC10271_00814(pamO_1) NCTC10271_03264(hapE_3) NCTC10271_05142(pamO_5)
MCEE : MCEL_14910 MCEL_41430
MMON : EWR22_10280 EWR22_23880
MHOL : K3U96_04590 K3U96_16490
MSEN : K3U95_17730 K3U95_23585
MPAE : K0O64_16545 K0O64_22500
MCRO : MI149_17455 MI149_22925
MAUS : JN090_10240 JN090_24605
MPAK : MIU77_10315 MIU77_11170
MJD : JDM601_0116 JDM601_3522
MTER : 4434518_00103(hapE_1) 4434518_03498(pamO_5)
MHIB : MHIB_29180 MHIB_33860
MHER : K3U94_00730 K3U94_10720 K3U94_19925
MVM : MJO54_00595 MJO54_19835
CCOE : CETAM_00300 CETAM_13030
RCR : NCTC10994_00950(pamO_1)
RKO : JWS14_20890 JWS14_20955
RHOO : RA302_30925 RA302_31665
ARTP : E5206_14685 E5206_14770
PSUL : AU252_00280 AU252_00335
BSPO : L1F31_01645 L1F31_01860
» show all
Taxonomy
Reference
Authors
Donoghue NA, Norris DB, Trudgill PW.
Title
The purification and properties of cyclohexanone oxygenase from Nocardia globerula CL1 and Acinetobacter NCIB 9871.
Journal
Reference
Authors
Sheng D, Ballou DP, Massey V.
Title
Mechanistic studies of cyclohexanone monooxygenase: chemical properties of intermediates involved in catalysis.
Journal
Reference
3
Authors
Stewart JD.
Title
Cyclohexanone monooxygenase: a useful reagent for asymmetric Baeyer-Villiger reactions.
Journal
Curr Org Chem 2:195-216 (1998)
Reference
4
Authors
Chen G, Kayser MM, Milhovilovic MD, Mrstik ME, Martinez CA, Stewart JD.
Title
Asymmetric oxidations at sulfur catalyzed by engineered strains that overexpress cyclohexanone monooxygenase.
Journal
New J Chem 23:827-832 (1999)
Reference
5
Authors
Ottolina G, Bianchi S, Belloni B, Carrea G, Danieli B.
Title
First asymmetric oxidation of tertiary amines by cyclohexanone monooxygenase.
Journal
Tetrahedron Lett 40:8483-8486 (1999)
Reference
6
Authors
Colonna S, Gaggero N, Carrea G, Ottolina G, Pasta P, Zambianchi F.
Title
First asymmetric epoxidation catalysed by cyclohexanone monooxygenase.
Journal
Tetrahedron Lett 43:1797-1799 (2002)
Other DBs
UM-BBD (Biocatalysis/Biodegradation Database): 1.14.13.22