KEGG   ORTHOLOGY: K03379
Entry
K03379                      KO                                     
Symbol
chnB
Name
cyclohexanone monooxygenase [EC:1.14.13.22]
Pathway
map00930  Caprolactam degradation
map01120  Microbial metabolism in diverse environments
map01220  Degradation of aromatic compounds
Brite
KEGG Orthology (KO) [BR:ko00001]
 09100 Metabolism
  09111 Xenobiotics biodegradation and metabolism
   00930 Caprolactam degradation
    K03379  chnB; cyclohexanone monooxygenase
Enzymes [BR:ko01000]
 1. Oxidoreductases
  1.14  Acting on paired donors, with incorporation or reduction of molecular oxygen
   1.14.13  With NADH or NADPH as one donor, and incorporation of one atom of oxygen into the other donor
    1.14.13.22  cyclohexanone monooxygenase
     K03379  chnB; cyclohexanone monooxygenase
Other DBs
RN: R02231 R06622
GO: 0018667
Genes
NHE: NECHADRAFT_48101 NECHADRAFT_54743 NECHADRAFT_82172
MAJ: MAA_06594
CMT: CCM_02795
MBE: MBM_08709
AFM: AFUA_2G09400
ACT: ACLA_081190
NFI: NFIA_041810 NFIA_084900
AOR: AO090011000330 AO090011000747
ANG: ANI_1_1806104(An12g05000)
AFV: AFLA_007728 AFLA_008145
LAB: LA76x_3343(chnB)
LAQ: GLA29479_2376(chnB)
PPX: T1E_5541
ACI: ACIAD2339
POL: Bpro_5565
AJS: Ajs_2102
SCL: sce4944
BJA: blr2938(blr2938) blr3857(blr3857) blr6984(blr6984)
BARH: WN72_16095
BVZ: BRAD3257_5765(pamO)
MALU: KU6B_59950
ALB: AEB_P2457
STEL: STAQ_29420
PUB: SAR11_0845(smo)
MBB: BCG_1454c
MAVI: RC58_01260
MBAI: MB901379_00225(ptlE_1) MB901379_00313(hapE_2)
MPHL: MPHLCCUG_02191(hapE_4)
MTHN: 4412656_03830(pamO_4)
MHAS: MHAS_03439(penE)
MAUU: NCTC10437_02096(hapE_7) NCTC10437_04678(pamO_7)
MMAG: MMAD_14180
MSAR: MSAR_38400
MAUB: MAUB_12640
MFLV: NCTC10271_00814(pamO_1) NCTC10271_03264(hapE_3) NCTC10271_05142(pamO_5)
MTER: 4434518_00103(hapE_1) 4434518_03498(pamO_5)
COK: COCCU_03205(pamO1) COCCU_12710(pamO3)
CCYC: SCMU_10760
RCR: NCTC10994_00950(pamO_1)
GOM: D7316_01709(ptlE)
NDA: Ndas_5034
PDX: Psed_0488
PSEA: WY02_02785
PSEH: XF36_18620
AG: BAA86293(chnB)
 » show all
Reference
  Authors
Iwaki H, Hasegawa Y, Teraoka M, Tokuyama T, Bergeron H, Lau PC
  Title
Identification of a transcriptional activator (ChnR) and a 6-oxohexanoate dehydrogenase (ChnE) in the cyclohexanol catabolic pathway in Acinetobacter sp. Strain NCIMB 9871 and localization of the genes that encode them.
  Journal
Appl Environ Microbiol 65:5158-62 (1999)
DOI:10.1128/AEM.65.11.5158-5162.1999
  Sequence

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_15735 MJO54_19835
MRFMJO55_02025 MJO55_22580
MPAAMKK62_01585 MKK62_16705 MKK62_23385 MKK62_23910 MKK62_25455
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
ASUNKG104_08860
PSULAU252_00280 AU252_00335
NDANdas_5034
NOABKM31_19730
NGNLCN96_44715
FREFranean1_3696
FRIFraEuI1c_4423
AMQAMETH_3876
PDXPsed_0488
PSEAWY02_02785
PSEHXF36_18620
CCAZCOUCH_26155
 » 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

KEGG   REACTION: R02231
Entry
R02231                      Reaction                               
Name
Cyclohexanone,NADPH:oxygen oxidoreductase (6-hydroxylating 1,2-lactonizing)
Definition
Cyclohexanone + Oxygen + NADPH + H+ <=> epsilon-Caprolactone + NADP+ + H2O
Equation
Reaction class
RC00001  C00005_C00006
RC00662  C00414_C01880
Enzyme
Pathway
rn00930  Caprolactam degradation
rn01120  Microbial metabolism in diverse environments
rn01220  Degradation of aromatic compounds
Orthology
K03379  cyclohexanone monooxygenase [EC:1.14.13.22]
Other DBs
RHEA: 24071

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