KEGG   ORTHOLOGY: K14520
Entry
K14520                      KO                                     

Symbol
hapE
Name
4-hydroxyacetophenone monooxygenase [EC:1.14.13.84]
Pathway
map00363  Bisphenol degradation
map01100  Metabolic pathways
map01120  Microbial metabolism in diverse environments
Brite
KEGG Orthology (KO) [BR:ko00001]
 09100 Metabolism
  09111 Xenobiotics biodegradation and metabolism
   00363 Bisphenol degradation
    K14520  hapE; 4-hydroxyacetophenone 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
    1.14.13.84  4-hydroxyacetophenone monooxygenase
     K14520  hapE; 4-hydroxyacetophenone monooxygenase
Other DBs
RN: R06892
GO: 0033767
Genes
PALK: PSAKL28_30880
GAG: Glaag_3898
GPS: C427_5372
HJA: BST95_01710
HALC: EY643_18055
BXE: Bxe_C0316
BXB: DR64_8118
BGE: BC1002_5820
PVE: UC34_06840
BHZ: ACR54_00614(hapE_3)
HYB: Q5W_23445
BJA: bll3180(bll3180)
BRS: S23_48170
BARH: WN72_17480
MMED: Mame_02139(hapE)
PZU: PHZ_c1807
RID: RIdsm_01107(hapE_3)
NAR: Saro_2452
SPHP: LH20_19445
SWI: Swit_2012
SPHD: HY78_15455
SPHM: G432_19880
SINB: SIDU_10910
SPHT: K426_23414
TMO: TMO_b0525
MAV: MAV_2805
MJL: Mjls_2770
MSIM: MSIM_50750
MSAK: MSAS_07860
MBAI: MB901379_02580(hapE_5)
MPSE: MPSD_28800
MSHJ: MSHI_13020
MPHL: MPHLCCUG_01020(hapE_2) MPHLCCUG_02619(hapE_6)
MTHN: 4412656_00667(hapE_1) 4412656_00952(hapE_2)
MHAS: MHAS_00653(hapE_1) MHAS_02465(hapE_2)
MAUU: NCTC10437_01662(hapE_4) NCTC10437_01669(hapE_5) NCTC10437_02731(hapE_9)
MMAG: MMAD_29640
MARZ: MARA_09020
MANY: MANY_43550
MAUB: MAUB_06770
MPOF: MPOR_21690
MPHU: MPHO_05910
MCHE: BB28_00510
MSAL: DSM43276_00081(hapE_2)
MTER: 4434518_03234(hapE_6)
NFA: NFA_33700
NFR: ERS450000_00683(hapE_3)
REY: O5Y_27880
ROP: ROP_25260
RHB: NY08_34
RFA: A3L23_03397(hapE_2)
RHS: A3Q41_04847(hapE_2)
RHU: A3Q40_00667(hapE_1)
RCR: NCTC10994_03316(hapE_4)
GRU: GCWB2_13960(hapE4)
GOM: D7316_04266(hapE_1) D7316_04655(hapE_2)
SALJ: SMD11_0682(hapE)
ARX: ARZXY2_4020(hapE)
AMYY: YIM_36680(hapE5) YIM_36800(hapE6)
PAUT: Pdca_05840
AG: AAK54073(hapA)
 » show all
Reference
  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
LinkDB

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
PALK: PSAKL28_30880
GAG: Glaag_3898
GPS: C427_5372
HJA: BST95_01710
HALC: EY643_18055
BXE: Bxe_C0316
BXB: DR64_8118
BGE: BC1002_5820
PVE: UC34_06840
BHZ: ACR54_00614(hapE_3)
HYB: Q5W_23445
BJA: bll3180(bll3180)
BRS: S23_48170
BARH: WN72_17480
MMED: Mame_02139(hapE)
PZU: PHZ_c1807
RID: RIdsm_01107(hapE_3)
NAR: Saro_2452
SPHP: LH20_19445
SWI: Swit_2012
SPHD: HY78_15455
SPHM: G432_19880
SINB: SIDU_10910
SPHT: K426_23414
TMO: TMO_b0525
MAV: MAV_2805
MJL: Mjls_2770
MSIM: MSIM_50750
MSAK: MSAS_07860
MBAI: MB901379_02580(hapE_5)
MPSE: MPSD_28800
MSHJ: MSHI_13020
MPHL: MPHLCCUG_01020(hapE_2) MPHLCCUG_02619(hapE_6)
MTHN: 4412656_00667(hapE_1) 4412656_00952(hapE_2)
MHAS: MHAS_00653(hapE_1) MHAS_02465(hapE_2)
MAUU: NCTC10437_01662(hapE_4) NCTC10437_01669(hapE_5) NCTC10437_02731(hapE_9)
MMAG: MMAD_29640
MARZ: MARA_09020
MANY: MANY_43550
MAUB: MAUB_06770
MPOF: MPOR_21690
MPHU: MPHO_05910
MCHE: BB28_00510
MSAL: DSM43276_00081(hapE_2)
MTER: 4434518_03234(hapE_6)
NFA: NFA_33700
NFR: ERS450000_00683(hapE_3)
REY: O5Y_27880
ROP: ROP_25260
RHB: NY08_34
RFA: A3L23_03397(hapE_2)
RHS: A3Q41_04847(hapE_2)
RHU: A3Q40_00667(hapE_1)
RCR: NCTC10994_03316(hapE_4)
GRU: GCWB2_13960(hapE4)
GOM: D7316_04266(hapE_1) D7316_04655(hapE_2)
SALJ: SMD11_0682(hapE)
ARX: ARZXY2_4020(hapE)
AMYY: YIM_36680(hapE5) YIM_36800(hapE6)
PAUT: Pdca_05840
 » 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
LinkDB

KEGG   REACTION: R06892
Entry
R06892                      Reaction                               

Name
(4-hydroxyphenyl)ethan-1-one,NADPH:oxygen oxidoreductase (ester-forming)
Definition
4'-Hydroxyacetophenone + NADPH + H+ + Oxygen <=> 4-Hydroxyphenyl acetate + NADP+ + H2O
Equation
Reaction class
RC00001  C00005_C00006
RC01644  C10700_C13636
Enzyme
Pathway
rn00363  Bisphenol degradation
rn01100  Metabolic pathways
rn01120  Microbial metabolism in diverse environments
Orthology
K14520  4-hydroxyacetophenone monooxygenase [EC:1.14.13.84]
Other DBs
RHEA: 22919
LinkDB

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