4-hydroxyacetophenone monooxygenase

4-hydroxyacetophenone monooxygenase
Identifiers
EC no.1.14.13.84
Databases
BRENDAenzyme data
ExPASyNiceZyme view
KEGGenzyme entry
MetaCycmetabolic pathway
Rheareactions
PDB structuresRCSB PDB PDBe PDBsum
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PMCarticles
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NCBIproteins

4-hydroxyacetophenone monooxygenase (EC 1.14.13.84) is an enzyme that catalyzes the chemical reaction:

+ NADPH + H+
 
 
O2
H2O
Rightward reaction arrow with minor substrate(s) from top left and minor product(s) to top right
 
 
 
2D representation of the chemical structure of Q27114157.
hydroquinone monoacetate
 

The four substrates of this enzyme are piceol (4-hydroxyacetophenone), reduced nicotinamide adenine dinucleotide phosphate (NADPH), oxygen, and a proton. Its products are hydroquinone monoacetate, oxidised NADP+, and water.[1][2]

This enzyme is a flavoprotein of Baeyer-Villiger monooxygenase type, which uses molecular oxygen as oxidant and incorporates one of its atoms into the starting material.[3] The systematic name of this enzyme class is (4-hydroxyphenyl)ethan-1-one,NADPH:oxygen oxidoreductase (ester-forming). This enzyme is also called HAPMO. It participates in bisphenol a degradation.[4]

References

  1. ↑ Enzyme 1.14.13.84 at KEGG Pathway Database.
  2. ↑ Kamerbeek NM, Olsthoorn AJ, Fraaije MW, Janssen DB (2003). "Substrate specificity and enantioselectivity of 4-hydroxyacetophenone monooxygenase". Appl. Environ. Microbiol. 69 (1): 419–26. Bibcode:2003ApEnM..69..419K. doi:10.1128/AEM.69.1.419-426.2003. PMC 152415. PMID 12514023.
  3. ↑ Janssen DB; Moonen, MJ; Van Der Ven, JG; Van Berkel, WJ; Fraaije, MW; Janssen, DB (2001). "4-Hydroxyacetophenone monooxygenase from Pseudomonas fluorescens ACB. A novel flavoprotein catalyzing Baeyer-Villiger oxidation of aromatic compounds" (PDF). Eur. J. Biochem. 268 (9): 2547–57. doi:10.1046/j.1432-1327.2001.02137.x. PMID 11322873.
  4. ↑ Prasad Kotharu; Lynda Ellis; Shawn Balcome. "Bisphenol A Pathway Map". Biocatalysis/Biodegradation Database. Retrieved 2015-11-04.