KEGG   ENZYME: 1.14.13.22
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
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]
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
ec00930  Caprolactam degradation
ec01120  Microbial metabolism in diverse environments
Orthology
K03379  cyclohexanone monooxygenase
Genes
NHENECHADRAFT_48101 NECHADRAFT_54743 NECHADRAFT_82172
MAJMAA_06594
CMTCCM_02795
MBEMBM_08709
AFMAFUA_2G09400
ACTACLA_081190
NFINFIA_041810 NFIA_084900
AORAO090011000330 AO090011000747
ANGANI_1_1806104(An12g05000)
AFVAFLA_007728 AFLA_008145
ALUCAKAW2_60896S
ACHEACHE_70177A
APUUAPUU_22001S APUU_51614S APUU_61080S APUU_80445A APUU_80806S
PCSPc14g01010 Pc16g10130
TRGTRUGW13939_01753
BGHBDBG_16891
PNOSNOG_04325
ZTRMYCGRDRAFT_71361
PFJMYCFIDRAFT_26387
FFUCLAFUR5_01541
BCOMBAUCODRAFT_119354
NPAUCRNP2_6897
LABLA76x_3343(chnB)
LAQGLA29479_2376(chnB)
PPXT1E_5541
PPJRK21_02867
ACIACIAD2339
SNANI6N98_12990
KIMG3T16_06295 G3T16_16875
HAAA5892_10460
BURBcep18194_C7142
BUEBRPE67_DCDS07380
BXEBxe_A3588 Bxe_C0276
BFZBAU07_12765
POLBpro_5565
AJSAjs_2102
GLCJQN73_12645 JQN73_12680
SCLsce4944
PLAPlav_0813 Plav_1165
BJAblr2938(blr2938) blr3857(blr3857) blr6984(blr6984)
BJUBJ6T_68290
BJPRN69_33125
BARHWN72_16095
BVZBRAD3257_5765(pamO)
BELBE61_03800
BDGLPJ38_17710
BSEPHAP48_0013325
BQBJ4P68_0017175
RBKE0H22_20215
TRBHB776_28720
LABTFIU93_30970
RUTFIU92_22370
CONTQ29_18925
SUAMBOO69_22545
SULDB5M07_18395
SPSESULPSESMR1_04140
MALUKU6B_59950
LVSLOKVESSMR4R_03944
NPNJI59_17840
SBARH5V43_03340
SPZRG5C33_18305
ALBAEB_P2457
SRFLHU95_14195
STELSTAQ_29420
PUBSAR11_0845(smo)
SNEANBZ79_19155
MBBBCG_1454c
MPAMAP_3509 MAP_3594
MAOMAP4_0179 MAP4_0267
MAVIRC58_01260
MAVURE97_00845 RE97_01270
MAVMAV_5119 MAV_5206
MITOCO_49430 OCO_50350
MIAOCU_49360 OCU_50280
MIDMIP_07484 MIP_07617
MYOOEM_49580 OEM_50550
MCHIAN480_25660 AN480_26135
MIROCQ_50420 OCQ_51340
MMALCKJ54_23545 CKJ54_24035
MMANMMAN_37520 MMAN_38540
MSAMycsm_02390 Mycsm_05176 Mycsm_05379
MULMUL_1053 MUL_4813
MMCMmcs_2024 Mmcs_4405
MKMMkms_2070 Mkms_4492
MJLMjls_2007 Mjls_4786
MMIMMAR_0309 MMAR_0403
MMAEMMARE11_02790 MMARE11_03660
MMMW7S_24740 W7S_25210
MLIMULP_00286 MULP_00391
MKNMKAN_15785 MKAN_18075
MYVG155_06310 G155_12075
MYEAB431_17350 AB431_22905
MGOAFA91_12585
MDXBTO20_22765 BTO20_29395
MSHGMSG_00233 MSG_00343
MFJMFLOJ_28280 MFLOJ_31730 MFLOJ_32760
MSTOMSTO_32130 MSTO_35750 MSTO_37030
MSIMMSIM_21360 MSIM_22330
MSAKMSAS_36170 MSAS_41630
MKUI2456_01715 I2456_03905
MGROFZ046_12885
MXEMYXE_48140
MNVMNVI_17890
MPAGC0J29_01755 C0J29_04175
MNMMNVM_17090 MNVM_25580
MGORH0P51_00630 H0P51_01600 H0P51_22560
MCOOMCOO_20200 MCOO_33860
MBAIMB901379_00225(ptlE_1) MB901379_00313(hapE_2)
MSEOMSEO_41360 MSEO_42390 MSEO_45730
MPSEMPSD_03990 MPSD_05030
MSHOMSHO_13500 MSHO_17780
MHEKJMUB5695_04644
MGAUMGALJ_07170 MGALJ_34870
MBRDMBRA_13790 MBRA_14670 MBRA_50180 MBRA_55600
MDFK0O62_07625
MMAMK3U93_01150
MHOLK3U96_04590 K3U96_16490
MHERK3U94_00730 K3U94_10720 K3U94_19925
MSENK3U95_11490 K3U95_17730 K3U95_23585
MPAEK0O64_16545 K0O64_22500
MOTLTS72_24340
MVMMJO54_00595 MJO54_19835
MRFMJO55_02025 MJO55_22580
MPAAMKK62_01585 MKK62_16705 MKK62_23385 MKK62_23910 MKK62_25455
MCROMI149_17455 MI149_22925 MI149_23720 MI149_23725
MSMMSMEG_2567 MSMEG_5625
MSGMSMEI_2507 MSMEI_5475
MSBLJ00_12775 LJ00_27815
MSNLI99_12775 LI99_27820
MSHLI98_12780 LI98_27825
MVAMvan_2243 Mvan_4961
MGIMflv_1789 Mflv_4103
MSPMspyr1_11730 Mspyr1_34460
MCBMycch_1987 Mycch_4342
MNED174_16985
MFTXA26_12580 XA26_24790
MPHLMPHLCCUG_02191(hapE_4)
MVQMYVA_2161 MYVA_4779
MRHMycrhN_2714 MycrhN_5746
MTHN4412656_03830(pamO_4)
MHASMHAS_03439(penE)
MDUMDUV_11450 MDUV_22700 MDUV_52170
MCHTMCHIJ_09730 MCHIJ_10150
MAUUNCTC10437_02096(hapE_7) NCTC10437_04678(pamO_7)
MMAGMMAD_14180
MMORMMOR_15380 MMOR_41870
MFXMFAL_26060
MAICMAIC_30420 MAIC_41250
MIJMINS_06910 MINS_27160
MALVMALV_14370 MALV_45430
MPSCMPSYJ_19010
MARZMARA_18060 MARA_24920
MGADMGAD_16890 MGAD_34050
MHEVMHEL_07900 MHEL_54040
MSARMSAR_38400
MAUBMAUB_12640
MPOFMPOR_25710 MPOR_50810
MMUCC1S78_011425 C1S78_018235
MMATMMAGJ_10310 MMAGJ_55580
MBOKMBOE_23300 MBOE_50050
MFGK6L26_07215 K6L26_18270 K6L26_20150
MSEIMSEDJ_26870 MSEDJ_28550
MFLVNCTC10271_00814(pamO_1) NCTC10271_03264(hapE_3) NCTC10271_05142(pamO_5)
MCEEMCEL_14910 MCEL_17530 MCEL_41430
MJDJDM601_0116 JDM601_3522
MTER4434518_00103(hapE_1) 4434518_03498(pamO_5)
MHIBMHIB_29180 MHIB_33860
MPAKMIU77_10315 MIU77_11170
CCOECETAM_00300 CETAM_12195(pamO) CETAM_13030
COKCOCCU_03205(pamO1) COCCU_12710(pamO3)
CCYCSCMU_10760
NNONONO_c42820
NWLNWFMUON74_28330
NGPLTT66_27615
RHARHA1_ro08137 RHA1_ro09035
RERRER_pREL1-02970
RCRNCTC10994_00950(pamO_1)
RKOJWS14_20890 JWS14_20955
RGOKYT97_06125
GOMD7316_01709(ptlE)
GAMGII34_19765
GPDGII33_03015
SPINKV203_08220
STRCAA958_29960
YIALO772_10810
MHOSCXR34_00670
MSFIT882_15880
CPHYB5808_20100
ARTPE5206_14770
PSULAU252_00280 AU252_00335
NDANdas_5034
NOABKM31_19730
NGNLCN96_44715
FREFranean1_3696
FRIFraEuI1c_4423
AMQAMETH_3876
PDXPsed_0488
PSEAWY02_02785
PSEHXF36_18620
 » show all
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 63:175-92 (1976)
DOI:10.1111/j.1432-1033.1976.tb10220.x
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 40:11156-67 (2001)
DOI:10.1021/bi011153h
Reference
3
  Authors
Stewart, J.D.
  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, 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 23:827-832 (1999)
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 40:8483-8486 (1999)
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 43:1797-1799 (2002)
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
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