KEGG   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
PALKPSAKL28_30880
GAGGlaag_3898
GPSC427_5372
HJABST95_01710
HALCEY643_18055
BXEBxe_C0316
BXBDR64_8118
BGEBC1002_5820
PVEUC34_06840
BHZACR54_00614(hapE_3)
BPDZBBN53_18555
AXYAXYL_05757
ADYHLG70_25065
HYBQ5W_23445
DIHG7047_24405
MESOBSQ44_24815
RHINGR_a03290
SAMESAMCFNEI73_pB0414
ESJSJ05684_a39130
RELREMIM1_PE00364
REIIE4771_PB00135
RTRRTCIAT899_PB00970
RGARGR602_PB00162
RJGCCGE525_34750
BJAbll3180(bll3180)
BJUBJ6T_65720
BJPRN69_31860
BRSS23_48170
BRCBCCGELA001_14335
BICLMTR13_10065
BRKCWS35_32470
BOTCIT37_37580
BRQCIT40_10485
BGQX265_25110
BGZXH91_23220
BSYMCIT39_09530
BBETF8237_04135
BARHWN72_17480
BVZBRAD3257_1812
BELBE61_38490
BDGLPJ38_18855
BSEPHAP48_0048135
BQBJ4P68_0007355
NTDEGO55_02615 EGO55_04725 EGO55_13890 EGO55_14155 EGO55_18115
MMEDMame_02139(hapE)
RBMTEF_09540 TEF_14660
PZUPHZ_c1807
PHBHYN04_07140
SMEDJNX03_16175
RIDRIdsm_01107(hapE_3)
NARSaro_2452
NPNJI59_09905 JI59_12755 JI59_17720 JI59_21965
NOVTQ38_027485 TQ38_027690
NOTC7W88_20535
NORFA702_19610
NOGGKE62_01765
SPHPLH20_19445
STERAOA14_07210
SWISwit_2012
SPHDHY78_15455
SPHMG432_19880
SMYBJP26_18750
SPKCKC8_02285 KC8_02340
SJPSJA_C2-05090
SINBSIDU_10910
SCHSphch_3468
SPMIK663_17836 K663_17946 K663_18141 K663_19768
SPHBEP837_01273(hapE) EP837_01276 EP837_03238 EP837_03267 EP837_03277 EP837_03339 EP837_03509
SPHTK426_23414
SPPHKFK14_08115
SPHJBSL82_08780
PALGHFP57_16470
SMICSmB9_21780 SmB9_37040
SANDH3309_16645
POQKZX46_02635 KZX46_17875
AEPAMC99_02079
ALHG6N82_11870
EFVCHH26_10020
ERRDVR09_13385
TMOTMO_b0525
MPAMAP_1441 MAP_1620
MAOMAP4_2219 MAP4_2403
MAVIRC58_11040 RC58_11945
MAVURE97_11050 RE97_11955
MAVMAV_2805
MITOCO_26400 OCO_28650
MIAOCU_26250 OCU_28510
MIDMIP_03698 MIP_04049
MYOOEM_24870 OEM_27100
MCHIAN480_10590 AN480_13895
MIROCQ_24960 OCQ_27230
MMALCKJ54_11925 CKJ54_13020
MMANMMAN_10250 MMAN_12600
MSAMycsm_03363
MMCMmcs_0310 Mmcs_1518 Mmcs_2740
MKMMkms_0320 Mkms_1541 Mkms_2784
MJLMjls_2770
MMIMMAR_2622 MMAR_2789
MMAEMMARE11_25410 MMARE11_27110
MMMW7S_12815 W7S_13885
MLIMULP_02355
MKNMKAN_00815
MYVG155_01790 G155_04185
MYEAB431_01805 AB431_15145
MDXBTO20_34235
MSHGMSG_02684 MSG_04454
MFJMFLOJ_05450 MFLOJ_51620 MFLOJ_54900
MSTOMSTO_06750 MSTO_59330
MSIMMSIM_50750
MSAKMSAS_07860
MKUI2456_13765
MGROFZ046_20310
MXEMYXE_38750 MYXE_42320
MNVMNVI_26500
MPAGC0J29_01040 C0J29_16070 C0J29_19310
MNMMNVM_19270 MNVM_28240
MGORH0P51_00695 H0P51_09335 H0P51_15105 H0P51_17885
MCOOMCOO_26190 MCOO_43040
MBAIMB901379_02580(hapE_5)
MSEOMSEO_12650 MSEO_14970
MPSEMPSD_28800
MSHOMSHO_39150 MSHO_41990
MHEKJMUB5695_03800
MGAUMGALJ_16320 MGALJ_22920
MLJMLAC_18560
MBRDMBRA_05320 MBRA_21050
MSHJMSHI_13020
MKRMKOR_36470
MDFK0O62_02210 K0O62_05035 K0O62_11570 K0O62_15825
MMAMK3U93_12890 K3U93_16480
MHOLK3U96_00470 K3U96_07055 K3U96_09595 K3U96_12435
MHERK3U94_18290
MSENK3U95_01840
MPAEK0O64_01410 K0O64_14620
MSPGF6B93_11555 F6B93_12080
MOTLTS72_10260
MSMMSMEG_2884
MSGMSMEI_2810
MSBLJ00_14345
MSNLI99_14350
MSHLI98_14355
MVAMvan_1842 Mvan_2883
MGIMflv_4506 Mflv_4557
MSPMspyr1_39050 Mspyr1_39570
MCBMycch_1506 Mycch_1583
MNED174_03215
MYNMyAD_03140
MFTXA26_03850 XA26_07900
MPHLMPHLCCUG_01020(hapE_2) MPHLCCUG_02619(hapE_6)
MVQMYVA_1658 MYVA_1697 MYVA_4982
MLLB1R94_01420 B1R94_12415
MRHMycrhN_4918
MTHN4412656_00667(hapE_1) 4412656_00952(hapE_2)
MHASMHAS_00653(hapE_1) MHAS_02465(hapE_2)
MDUMDUV_26540 MDUV_26740
MCHTMCHIJ_02010 MCHIJ_02120 MCHIJ_08790 MCHIJ_12830
MAUUNCTC10437_01662(hapE_4) NCTC10437_01669(hapE_5) NCTC10437_02731(hapE_9)
MMAGMMAD_29640
MMORMMOR_00710 MMOR_10050 MMOR_26730 MMOR_33780 MMOR_47920
MFXMFAL_09770 MFAL_26200
MAICMAIC_26710 MAIC_53440
MIJMINS_06790 MINS_26620
MALVMALV_29370 MALV_32190
MTYMTOK_12030
MPSCMPSYJ_47990
MARZMARA_09020
MGADMGAD_01030 MGAD_08510
MHEVMHEL_19100 MHEL_50050 MHEL_59170
MSARMSAR_18520 MSAR_41410
MANYMANY_43550
MAUBMAUB_06770
MPOFMPOR_21690
MPHUMPHO_05910
MMUCC1S78_015375 C1S78_019285
MMATMMAGJ_17560
MBOKMBOE_16070 MBOE_19840
MFGK6L26_27725 K6L26_29615
MSEIMSEDJ_42750
MFLVNCTC10271_02178(hapE_2)
MCHEBB28_00510
MSALDSM43276_00081(hapE_2)
MJDJDM601_3248 JDM601_4258
MTER4434518_03234(hapE_6)
MMINMMIN_06780 MMIN_09430
MHIBMHIB_23920 MHIB_26590
MPAKMIU77_08125
CCYCSCMU_01920 SCMU_38690
NFANFA_33700
NFRERS450000_00683(hapE_3)
NNONONO_c26450 NONO_c26620 NONO_c26820 NONO_c27210
NOZDMB37_03490
RHARHA1_ro05396
REYO5Y_27880
RQIC1M55_29730
ROPROP_25260
REQREQ_13640 REQ_45280
RHBNY08_34
RFAA3L23_03397(hapE_2)
RHSA3Q41_04847(hapE_2)
RRZCS378_11525
RHUA3Q40_00667(hapE_1)
RHODAOT96_09385
RCRNCTC10994_03316(hapE_4)
RKOJWS14_03735 JWS14_13900 JWS14_43780 JWS14_44120 JWS14_44420
GORKTR9_0546 KTR9_2191 KTR9_3188
GTABCM27_04875 BCM27_11715 BCM27_16285 BCM27_19035
GRUGCWB2_13960(hapE4)
GOMD7316_04266(hapE_1) D7316_04655(hapE_2)
GAVC5O27_14130
GODGKZ92_12830
GPDGII33_20030
GJIH1R19_00410 H1R19_10915 H1R19_19295
DIZCT688_05610
TOYFO059_17465
SCADDN051_01765
SALJSMD11_0682(hapE)
SPLACP981_11500
MIOAOA12_02825 AOA12_13430 AOA12_19215
MRNK8F61_04945
LEULeucomu_12905
ARZAUT26_19680 AUT26_19745
ARXARZXY2_4020(hapE)
ARTPE5206_14925 E5206_18210
AJGKKR91_13970
GLUF0M17_15875 F0M17_15940
GPRJQN66_16310 JQN66_16375
PAEYKUF55_15805 KUF55_16730
AEZC3E78_14050
NOABKM31_13265
FRIFraEuI1c_2106 FraEuI1c_3128 FraEuI1c_3915
SACGFDZ84_29950 FDZ84_37130
AMYYYIM_36680(hapE5) YIM_36800(hapE6)
AACDLWP59_17040
PDXPsed_2079 Psed_2677
PAUTPdca_05840
PBROHOP40_17195
SSYIEKG83_16290 EKG83_27315
ABAIIMCC26256_11166 IMCC26256_111801
BSOLFSW04_06275 FSW04_06440 FSW04_20620
AYMYM304_37530
ATQGH723_04715
AQZKSP35_01975
IAMHC251_23265
TBHTbon_00650
 » 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
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
  Sequence
Other DBs
ExplorEnz - The Enzyme Database: 1.14.13.84
IUBMB Enzyme Nomenclature: 1.14.13.84
ExPASy - ENZYME nomenclature database: 1.14.13.84
BRENDA, the Enzyme Database: 1.14.13.84
CAS: 156621-13-5

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