ArticleApplied and environmental microbiology2003
Substrate specificity and enantioselectivity of 4-hydroxyacetophenone monooxygenase.
Article in Applied and environmental microbiology, 2003. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 20 papers.
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Who cites it
20 citing papers in PubMed, 110 citations in OpenAlex.
- The Flexible Peripheral Segments Modulate the Catalytic Activity of the FAD-Containing Monooxygenase EthA fromBiomolecules · 2026Article
- Surveying aIranian journal of microbiology · 2026Article
- Discovery of Two Native Baeyer-Villiger Monooxygenases for Asymmetric Synthesis of Bulky Chiral Sulfoxides.Applied and environmental microbiology · 2018Article
- Cloning and characterization of the Type I Baeyer-Villiger monooxygenase from Leptospira biflexa.AMB Express · 2017Article
- Biosynthetic pathway of aliphatic formates via a Baeyer-Villiger oxidation in mechanism present in astigmatid mites.Proceedings of the National Academy of Sciences of the United States of America · 2017Article
- Characterization and Crystal Structure of a Robust Cyclohexanone Monooxygenase.Angewandte Chemie (International ed. in English) · 2016Article
- Substitution of a Single Amino Acid Reverses the Regiospecificity of the Baeyer-Villiger Monooxygenase PntE in the Biosynthesis of the Antibiotic Pentalenolactone.Biochemistry · 2016Article
- Article
- The Origin and Evolution of Baeyer-Villiger Monooxygenases (BVMOs): An Ancestral Family of Flavin Monooxygenases.PloS one · 2015Article
- A Fluorescent Bioreporter for Acetophenone and 1-Phenylethanol derived from a Specifically Induced Catabolic Operon.Frontiers in microbiology · 2015Article
- Elucidation of the upper pathway of alicyclic musk Romandolide degradation in OECD screening tests with activated sludge.Environmental science and pollution research international · 2014Article
- Cloning, overexpression and biocatalytic exploration of a novel Baeyer-Villiger monooxygenase from Aspergillus fumigatus Af293.AMB Express · 2013Article
- Isolation and characterization of a novel Rhodococcus strain with switchable carbonyl reductase and para-acetylphenol hydroxylase activities.Journal of industrial microbiology & biotechnology · 2013Article
- Two enzymes of a complete degradation pathway for linear alkylbenzenesulfonate (LAS) surfactants: 4-sulfoacetophenone Baeyer-Villiger monooxygenase and 4-sulfophenylacetate esterase in Comamonas testosteroni KF-1.Applied and environmental microbiology · 2012Article
- Mapping the substrate binding site of phenylacetone monooxygenase from Thermobifida fusca by mutational analysis.Applied and environmental microbiology · 2011Article
- Cloning, expression, characterization, and biocatalytic investigation of the 4-hydroxyacetophenone monooxygenase from Pseudomonas putida JD1.Applied and environmental microbiology · 2009Article
- Isolation of Rhodococcus sp. strain ECU0066, a new sulfide monooxygenase-producing strain for asymmetric sulfoxidation.Applied and environmental microbiology · 2009Article
- Elucidation of the 4-hydroxyacetophenone catabolic pathway in Pseudomonas fluorescens ACB.Journal of bacteriology · 2008Article
- Hydroquinone dioxygenase from pseudomonas fluorescens ACB: a novel member of the family of nonheme-iron(II)-dependent dioxygenases.Journal of bacteriology · 2008Article
- Degradation of Bis(4-Hydroxyphenyl)methane (bisphenol F) by Sphingobium yanoikuyae strain FM-2 isolated from river water.Applied and environmental microbiology · 2008Article
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Authors and funding
4 authors at 1 institution in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
The 4-hydroxyacetophenone monooxygenase (HAPMO) from Pseudomonas fluorescens ACB catalyzes NADPH- and oxygen-dependent Baeyer-Villiger oxidation of 4-hydroxyacetophenone to the corresponding acetate ester. Using the purified enzyme from recombinant Escherichia coli, we found that a broad range of carbonylic compounds that are structurally more or less similar to 4-hydroxyacetophenone are also substrates for this flavin-containing monooxygenase. On the other hand, several carbonyl compounds that are substrates for other Baeyer-Villiger monooxygenases (BVMOs) are not converted by HAPMO. In addition to performing Baeyer-Villiger reactions with aromatic ketones and aldehydes, the enzyme was also able to catalyze sulfoxidation reactions by using aromatic sulfides. Furthermore, several heterocyclic and aliphatic carbonyl compounds were also readily converted by this BVMO. To probe the enantioselectivity of HAPMO, the conversion of bicyclohept-2-en-6-one and two aryl alkyl sulfides was studied. The monooxygenase preferably converted (1R,5S)-bicyclohept-2-en-6-one, with an enantiomeric ratio (E) of 20, thus enabling kinetic resolution to obtain the (1S,5R) enantiomer. Complete conversion of both enantiomers resulted in the accumulation of two regioisomeric lactones with moderate enantiomeric excess (ee) for the two lactones obtained [77% ee for (1S,5R)-2 and 34% ee for (1R,5S)-3]. Using methyl 4-tolyl sulfide and methylphenyl sulfide, we found that HAPMO is efficient and highly selective in the asymmetric formation of the corresponding (S)-sulfoxides (ee > 99%). The biocatalytic properties of HAPMO described here show the potential of this enzyme for biotechnological applications.
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