KEGG ENZYME: 1.14.13.22

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

FOX:	FOXG_16975

NHE:	NECHADRAFT_48101 NECHADRAFT_54743 NECHADRAFT_82172

FFC:	NCS54_00480900

FKR:	NCS57_00517800

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)

MAJ:

MAA_06594

MBRN:

26246769(BVMO)

CMT:

CCM_02795

CFJ:	CFIO01_10029

CLUP:

CLUP02_16323

PFY:	PFICI_11131

MBE:

MBM_08709

AFM:	AFUA_2G09400

ACT:	ACLA_081190

NFI:	NFIA_041810 NFIA_084900

AOR:	AO090011000330 AO090011000747

ANG:	An12g05000

AFV:	AFLA_007728 AFLA_008145

ALUC:

AKAW2_60896S

ACHE:

ACHE_70177A

APUU:

APUU_22001S APUU_51614S APUU_61080S APUU_80445A APUU_80806S

PCS:	N7525_000103 N7525_010738

TRG:	TRUGW13939_01753

BGH:	BDBG_16891

PNO:	SNOG_04325

ZTR:	MYCGRDRAFT_71361

PFJ:	MYCFIDRAFT_26387

FFU:	CLAFUR5_01541

CBET:

CB0940_00783 CB0940_05932

BCOM:

BAUCODRAFT_119354

NPA:	UCRNP2_6897

TASA:

A1Q1_00648

CCAC:

CcaHIS019_0106420(CcaverHIS019_0106420)

LAB:	LA76x_3343(chnB)

LAQ:	GLA29479_2376(chnB)

DYG:	DYGSA30_26200

PPX:

T1E_5541

PPJ:	RK21_02867

SNAN:

I6N98_12990

KIM:	G3T16_06295 G3T16_16875

HAA:	A5892_10460

SOK:	D0B54_07505

POL:

Bpro_5565

AJS:

Ajs_2102

ATEM:

PQV96_11845

HCZ:	G9Q37_07255

MMED:

Mame_00789

LABT:

FIU93_30970

RUT:	FIU92_22370

CON:	TQ29_18925

SUAM:

BOO69_22545

SULD:

B5M07_18395

SPSE:

SULPSESMR1_04140

MALU:

KU6B_59950

LVS:	LOKVESSMR4R_03944

NPN:	JI59_17840

NRE:	BES08_11410

NOV:	TQ38_015225

SPHA:

D3Y57_02320

SNAP:

PQ455_08140 PQ455_18135

SPHR:

BSY17_3717

SYA:	A6768_20635

SBAR:

H5V43_03340

SPAG:

sphantq_04479

SPHG:

AZE99_00725

BLAS:

BSY18_771

BFW:	B5J99_13040

SPZR:

G5C33_14315 G5C33_18305

ALB:

AEB_P2457

MPA:	MAP_3509 MAP_3594

MAO:	MAP4_0179 MAP4_0267

MAVI:

RC58_01260

MAVU:

RE97_00845 RE97_01270

MAV:	MAV_5119 MAV_5206

MIT:	OCO_49430 OCO_50350

MIA:	OCU_49360 OCU_50280

MID:	MIP_07484 MIP_07617

MYO:	OEM_49580 OEM_50550

MCHI:

AN480_25660 AN480_26135

MIR:	OCQ_50420 OCQ_51340

MMAL:

CKJ54_23545 CKJ54_24035

MMAN:

MMAN_37520 MMAN_38540

MSER:

MTY59_09370 MTY59_12810 MTY59_13830

MSA:	Mycsm_02390 Mycsm_05176 Mycsm_05379

MUL:	MUL_1053 MUL_4813

MMI:	MMAR_0309 MMAR_0403

MMAE:

MMARE11_02790 MMARE11_03660

MLI:	MULP_00286 MULP_00391

MPSE:

MPSD_03990 MPSD_05030

MSHO:

MSHO_13500 MSHO_17780

MMC:	Mmcs_2024 Mmcs_4405

MKM:	Mkms_2070 Mkms_4492

MJL:	Mjls_2007 Mjls_4786

MMM:	W7S_24740 W7S_25210

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

MXE:	MYXE_48140

MNV:	MNVI_17890

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

MHEK:

JMUB5695_04644

MGAU:

MGALJ_07170 MGALJ_34870

MBRD:

MBRA_13790 MBRA_14670 MBRA_50180 MBRA_55600

MMAM:

K3U93_01150

MOT:	LTS72_24340

MPAA:

MKK62_01585 MKK62_23385 MKK62_23910 MKK62_25455

MKY:	IWGMT90018_03150

MADI:

A7U43_23385

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

MVA:	Mvan_2243 Mvan_4961

MGI:	Mflv_1789 Mflv_4103

MSP:	Mspyr1_11730 Mspyr1_34460

MCB:	Mycch_1987 Mycch_4342

MNE:	D174_16985

MFT:	XA26_12580 XA26_24790

MPHL:

MPHLCCUG_02191(hapE_4)

MVQ:	MYVA_2161 MYVA_4779

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)

MMAG:

MMAD_14180

MMOR:

MMOR_15380 MMOR_41870

MFX:	MFAL_26060

MAIC:

MAIC_30420 MAIC_41250

MIJ:	MINS_06910

MALV:

MALV_14370 MALV_45430

MPSC:

MPSYJ_19010

MARZ:

MARA_18060 MARA_24920

MGAD:

MGAD_16890 MGAD_34050

MHEV:

MHEL_07900 MHEL_54040

MSAR:

MSAR_38400

MAUB:

MAUB_12640

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

MGO:	AFA91_12585

MHOL:

K3U96_04590 K3U96_16490

MSEN:

K3U95_17730 K3U95_23585

MPAE:

K0O64_16545 K0O64_22500

MRF:	MJO55_22580

MDF:	K0O62_07625

MCRO:

MI149_17455 MI149_22925

MGRO:

FZ046_12885

MAUS:

JN090_10240 JN090_24605

MFRE:

EXE63_07995

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

NNO:	NONO_c42820

NWL:	NWFMUON74_28330

NGP:	LTT66_27615

RER:	RER_pREL1-02970

RCR:	NCTC10994_00950(pamO_1)

RKO:	JWS14_20890 JWS14_20955

RGO:	KYT97_06125

RPSK:

JWS13_42180

RHOP:

D8W71_21070

RHOO:

RA302_30925 RA302_31665

RHOJ:

JVH1_20220

PDEF:

P9209_05625

GOM:	D7316_01709(ptlE)

GAM:	GII34_19765

GPD:	GII33_03015

SPIN:

KV203_08220

SGRF:

SGFS_003010

STRC:

AA958_29960

SCHG:

NRO40_23360

STSD:

HEP87_07105

YIA:	LO772_10810

MHOS:

CXR34_00670

MSF:	IT882_15880

CPHY:

B5808_20100

GMN:	GMOLON4_1492(chnB)

ARTP:

E5206_14685 E5206_14770

AOD:	Q8Z05_16880

PSUL:

AU252_00280 AU252_00335

GMY:

XH9_01105

CCYC:

SCMU_10760

JAY:	H7A72_06400

BSPO:

L1F31_01645 L1F31_01860

NDA:

Ndas_5034

NAKE:

KGD83_26635

ACTW:

F7P10_38375

NOA:	BKM31_19730

MHAI:

OHB01_22685

FRE:	Franean1_3696

FRI:	FraEuI1c_4423

BLAP:

MVA48_04330

AMQ:	AMETH_3876

PDX:	Psed_0488 Psed_2233

PSEA:

WY02_02785

PSEH:

XF36_18620

PPEL:

H6H00_19430

ACTY:

OG774_12495

EKE:	EK0264_02335

SBAE:

DSM104329_02047

» 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

Authors

Stewart JD.

Title

Cyclohexanone monooxygenase: a useful reagent for asymmetric Baeyer-Villiger reactions.

Journal

Curr Org Chem 2:195-216 (1998)

Reference

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

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

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

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

DBGET integrated database retrieval system