KEGG ENZYME: 1.14.13.84

ENZYME: 1.14.13.84

Entry

EC 1.14.13.84               Enzyme

Name

4-hydroxyacetophenone monooxygenase;
HAPMO

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

(4-hydroxyphenyl)ethan-1-one,NADPH:oxygen oxidoreductase (ester-forming)

Reaction(IUBMB)

(4-hydroxyphenyl)ethan-1-one + NADPH + H+ + O2 = 4-hydroxyphenyl acetate + NADP+ + H2O [RN:R06892]

Reaction(KEGG)

R06892

Substrate

(4-hydroxyphenyl)ethan-1-one [CPD:C10700];
NADPH [CPD:C00005];
H+ [CPD:C00080];
O2 [CPD:C00007]

Product

4-hydroxyphenyl acetate [CPD:C13636];
NADP+ [CPD:C00006];
H2O [CPD:C00001]

Comment

Contains FAD. The enzyme from Pseudomonas fluorescens ACB catalyses the conversion of a wide range of acetophenone derivatives. Highest activity occurs with compounds bearing an electron-donating substituent at the para position of the aromatic ring [1]. In the absence of substrate, the enzyme can act as an NAD(P)H oxidase (EC 1.6.3.1).

History

EC 1.14.13.84 created 2004

Pathway

ec00363

Bisphenol degradation

ec01100

Metabolic pathways

ec01120

Microbial metabolism in diverse environments

Orthology

K14520

4-hydroxyacetophenone monooxygenase

Genes

PALK:

PSAKL28_30880

GAG:	Glaag_3898

GPS:

C427_5372

HJA:	BST95_01710

HALC:

EY643_18055

CUK:	KB879_33605

BXE:

Bxe_C0316

BXB:

DR64_8118

BGE:	BC1002_5820

PVE:	UC34_06840

BHZ:	ACR54_00614(hapE_3)

BPDZ:

BBN53_18555

AXY:	AXYL_05757

ADY:	HLG70_25065

APES:

FOC84_16990

AAEG:

RA224_03845

HYB:

Q5W_23445

DIH:	G7047_24405

MESO:

BSQ44_24815

CHEA:

PVE73_18625

RHI:	NGR_a03290

SAME:

SAMCFNEI73_pB0414

ESJ:	SJ05684_a39130

REL:	REMIM1_PE00364

REI:	IE4771_PB00135

RTR:	RTCIAT899_PB00970

RGA:	RGR602_PB00162

RJG:	CCGE525_34750

BJA:	bll3180(bll3180)

BJU:	BJ6T_65720

BJP:	RN69_31860

BRS:

S23_48170

BRC:	BCCGELA001_14335

BIC:	LMTR13_10065

BRK:	CWS35_32470

BOT:	CIT37_37580

BRQ:	CIT40_10485

BGQ:	X265_25110

BGZ:	XH91_23220

BSYM:

CIT39_09530

BBET:

F8237_04135

BARH:

WN72_17480

BVZ:	BRAD3257_1812

BEL:	BE61_38490

BDG:	LPJ38_18855

BSEP:

HAP48_0048135

BQB:	J4P68_0007355

BBAN:

J4G43_018415

BAUT:

QA635_14830

BBRA:

QA636_14590

BGK:	IC762_25630

BCOU:

IC761_23575

BPAH:

QA639_30255

BXN:	I3J27_12310

BROS:

QUH67_11180

BRAZ:

LRP30_14055

MMED:

Mame_02139(hapE)

RBM:	TEF_09540 TEF_14660

PZU:

PHZ_c1807

PHB:	HYN04_07140

SMED:

JNX03_16175

RID:	RIdsm_01107(hapE_3)

NAR:

Saro_2452

NPN:	JI59_09905 JI59_12755 JI59_17720 JI59_21965

NOV:	TQ38_027485 TQ38_027690

NOT:	C7W88_20535

NOR:	FA702_19610

NOG:	GKE62_01765

SPHP:

LH20_19445

STER:

AOA14_07210

SWI:

Swit_2012

SPHD:

HY78_15455

SPHM:

G432_19880

SMY:	BJP26_18750

SPKC:

KC8_02285 KC8_02340

SJP:	SJA_C2-05090

SINB:

SIDU_10910

SCH:	Sphch_3468

SPMI:

K663_17836 K663_17946 K663_18141 K663_19768

SPHB:

EP837_01273(hapE) EP837_01276 EP837_03238 EP837_03267 EP837_03277 EP837_03339 EP837_03509

SPHT:

K426_23414

SPPH:

KFK14_08115

SPHJ:

BSL82_08780

PALG:

HFP57_16470

SMIC:

SmB9_21780 SmB9_37040

SAND:

H3309_16645

POQ:	KZX46_02635 KZX46_17875

PMEA:

KTC28_16080

AEP:	AMC99_02079

ALH:	G6N82_11870

EFV:	CHH26_10020

ERR:	DVR09_13385

NTD:	EGO55_02615 EGO55_04725 EGO55_13890 EGO55_14155 EGO55_18115

TMO:

TMO_b0525

MPA:

MAP_1620

MAO:

MAP4_2219

MAVI:

RC58_11040

MAVU:

RE97_11050

MAV:

MAV_2805

MIT:

OCO_26400

MIA:

OCU_26250

MID:

MIP_04049

MYO:

OEM_24870

MCHI:

AN480_10590 AN480_13895

MIR:

OCQ_24960

MMAL:

CKJ54_11925

MMAN:

MMAN_12600

MSA:	Mycsm_03363

MMI:	MMAR_2622 MMAR_2789

MMAE:

MMARE11_25410 MMARE11_27110

MLI:	MULP_02355

MPSE:

MPSD_28800

MSHO:

MSHO_39150 MSHO_41990

MMC:	Mmcs_1518 Mmcs_2740

MKM:	Mkms_1541 Mkms_2784

MJL:

Mjls_2770

MMM:

W7S_12815

MKN:	MKAN_00815

MYV:	G155_01790

MYE:	AB431_01805

MDX:	BTO20_34235

MSHG:

MSG_02684 MSG_04454

MFJ:	MFLOJ_05450 MFLOJ_51620 MFLOJ_54900

MSTO:

MSTO_06750 MSTO_59330

MSIM:

MSIM_50750

MSAK:

MSAS_07860

MKU:	I2456_13765

MLW:	MJO58_14125 MJO58_19375

MXE:	MYXE_38750 MYXE_42320

MNV:	MNVI_26500

MPAG:

C0J29_01040 C0J29_16070

MNM:	MNVM_28240

MGOR:

H0P51_00695 H0P51_09335 H0P51_15105

MCOO:

MCOO_43040

MBAI:

MB901379_02580(hapE_5)

MSEO:

MSEO_14970

MHEK:

JMUB5695_03800

MGAU:

MGALJ_16320

MLJ:	MLAC_18560

MBRD:

MBRA_05320

MSHJ:

MSHI_13020

MMAM:

K3U93_12890 K3U93_16480

MSPG:

F6B93_11555 F6B93_12080

MOT:	LTS72_10260

MPAA:

MKK62_19500 MKK62_25885

MKY:	IWGMT90018_29320 IWGMT90018_35310 IWGMT90018_47580

MADI:

A7U43_00820 A7U43_19685

MWU:	PT015_22885

MVA:

Mvan_1842

MGI:

Mflv_4506

MSP:	Mspyr1_39050

MCB:	Mycch_1506

MNE:	D174_03215

MYN:	MyAD_03140

MFT:	XA26_03850

MPHL:

MPHLCCUG_01020(hapE_2)

MVQ:	MYVA_1697 MYVA_4982

MLL:	B1R94_01420 B1R94_12415

MRH:	MycrhN_4918

MTHN:

4412656_00667(hapE_1)

MHAS:

MHAS_00653(hapE_1)

MDU:	MDUV_26540

MCHT:

MCHIJ_02010 MCHIJ_02120 MCHIJ_08790

MAUU:

NCTC10437_01662(hapE_4) NCTC10437_01669(hapE_5)

MMAG:

MMAD_29640

MMOR:

MMOR_00710 MMOR_10050 MMOR_33780 MMOR_47920

MFX:	MFAL_09770 MFAL_26200

MAIC:

MAIC_53440

MIJ:	MINS_06790 MINS_26620

MALV:

MALV_32190

MTY:	MTOK_12030

MPSC:

MPSYJ_47990

MARZ:

MARA_09020

MGAD:

MGAD_08510

MHEV:

MHEL_19100 MHEL_59170

MSAR:

MSAR_18520

MANY:

MANY_43550

MAUB:

MAUB_06770

MPOF:

MPOR_21690

MPHU:

MPHO_05910

MMUC:

C1S78_015375

MMAT:

MMAGJ_17560

MBOK:

MBOE_16070

MFG:	K6L26_29615

MSEI:

MSEDJ_42750

MCEE:

MCEL_41620

MMON:

EWR22_07725 EWR22_14555

MHOL:

K3U96_00470 K3U96_07055 K3U96_12435

MSEN:

K3U95_01840

MPAE:

K0O64_01410

MRF:	MJO55_08255

MDF:	K0O62_02210 K0O62_05035 K0O62_11570

MCRO:

MI149_01945

MGRO:

FZ046_20310

MPAK:

MIU77_08125

MCHE:

BB28_00510

MSAL:

DSM43276_00081(hapE_2)

MJD:	JDM601_3248

MTER:

4434518_03234(hapE_6)

MMIN:

MMIN_09430

MHIB:

MHIB_26590

MHER:

K3U94_18290

MVM:	MJO54_18455

CCYC:

SCMU_01920 SCMU_38690

NFA:

NFA_33700

NFR:	ERS450000_00683(hapE_3)

NNO:	NONO_c26450 NONO_c26620 NONO_c26820 NONO_c27210

NOZ:	DMB37_03490

RHA:	RHA1_ro05396

REY:

O5Y_27880

RQI:	C1M55_29730

ROP:

ROP_25260

RHB:

NY08_34

RFA:	A3L23_03397(hapE_2)

RHS:	A3Q41_04847(hapE_2)

RRZ:	CS378_11525

RHU:	A3Q40_00667(hapE_1)

RHOD:

AOT96_09385

RCR:	NCTC10994_03316(hapE_4)

RKO:	JWS14_03735 JWS14_13900 JWS14_43780 JWS14_44120 JWS14_44420

ROZ:	CBI38_08630 CBI38_34625

RPSK:

JWS13_12455 JWS13_31690

RANT:

RHODO2019_18180

REQ:

REQ_45280

GOR:	KTR9_0546 KTR9_2191 KTR9_3188

GTA:	BCM27_04875 BCM27_11715 BCM27_16285 BCM27_19035

GRU:	GCWB2_13960(hapE4)

GOM:	D7316_04266(hapE_1) D7316_04655(hapE_2)

GAV:	C5O27_14130

GOD:	GKZ92_12830

GPD:	GII33_20030

GJI:	H1R19_00410 H1R19_10915 H1R19_19295

GHN:	MVF96_11115

GAMI:

IHQ52_16570

GMG:	NWF22_20955

DIZ:	CT688_05610

TOY:	FO059_17465

SCAD:

DN051_01765

SALJ:

SMD11_0682(hapE)

SPLA:

CP981_11500

MIO:	AOA12_02825 AOA12_13430 AOA12_19215

MRN:	K8F61_04945

MSUW:

GCM10025863_18850

LEU:	Leucomu_12905

ARZ:	AUT26_19680 AUT26_19745

ARX:	ARZXY2_4020(hapE)

ARTP:

E5206_14925 E5206_18210

AJG:	KKR91_13970

AGEG:

MUG94_16715

AKO:	N9A08_13055

AJR:	N2K98_15340

GLU:	F0M17_15875 F0M17_15940

GPR:	JQN66_16310 JQN66_16375

GNC:	QQS42_16535 QQS42_16600

PAEY:

KUF55_15805 KUF55_16730

AEZ:	C3E78_14050

ACTQ:

OG417_12765

NOA:	BKM31_13265

FRI:	FraEuI1c_2106 FraEuI1c_3128 FraEuI1c_3915

NAKA:

H7F38_05510

SACG:

FDZ84_29950 FDZ84_37130

AMYY:

YIM_36800(hapE6)

AACD:

LWP59_17040

PDX:	Psed_2079 Psed_2677

PAUT:

Pdca_05840

PBRO:

HOP40_17195

PPEL:

H6H00_16815 H6H00_19165

SSYI:

EKG83_16290 EKG83_27315

ACTY:

OG774_14300

ABAI:

IMCC26256_11166 IMCC26256_111801

BSOL:

FSW04_06275 FSW04_06440 FSW04_20620

AYM:	YM304_37530

ATQ:	GH723_04715

AQZ:	KSP35_01975

IAM:	HC251_23265

DHI:	LH044_14145

TBH:	Tbon_00650

TFLA:

O0235_13525

» show all

Reference

1 [PMID:11322873]

Authors

Kamerbeek NM, Moonen MJ, Van Der Ven JG, Van Berkel WJ, Fraaije MW, Janssen DB

Title

4-Hydroxyacetophenone monooxygenase from Pseudomonas fluorescens ACB. A novel flavoprotein catalyzing Baeyer-Villiger oxidation of aromatic compounds.

Journal

Eur J Biochem 268:2547-57 (2001)
DOI:10.1046/j.1432-1327.2001.02137.x

Sequence

[ag:AAK54073]

Reference

2 [PMID:12514023]

Authors

Kamerbeek NM, Olsthoorn AJ, Fraaije MW, Janssen DB.

Title

Substrate specificity and enantioselectivity of 4-hydroxyacetophenone monooxygenase.

Journal

Appl Environ Microbiol 69:419-26 (2003)
DOI:10.1128/AEM.69.1.419-426.2003