Staff Publications

Staff Publications

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    'Staff publications' is the digital repository of Wageningen University & Research

    'Staff publications' contains references to publications authored by Wageningen University staff from 1976 onward.

    Publications authored by the staff of the Research Institutes are available from 1995 onwards.

    Full text documents are added when available. The database is updated daily and currently holds about 240,000 items, of which 72,000 in open access.

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Record number 109714
Title 19F NMR study on the biological Baeyer-Villiger oxidation of acetophenones
Author(s) Moonen, M.J.H.; Rietjens, I.M.C.M.; Berkel, W.J.H. van
Source Journal of Industrial Microbiology and Biotechnology 26 (2001). - ISSN 1367-5435 - p. 35 - 42.
Department(s) Biochemistry
Publication type Refereed Article in a scientific journal
Publication year 2001
Abstract The biological Baeyer-Villiger oxidation of acetophenones was studied by 19F nuclear magnetic resonance (NMR). The 19F NMR method was used to characterise the time-dependent conversion of various fluorinated acetophenones in either whole cells of Pseudomonas fluorescens ACB or in incubations with purified 4'-hydroxyacetophenone monooxygenase (HAPMO). Whole cells of P. fluorescens ACB converted 4'-fluoroacetophenone to 4-fluorophenol and 4'-fluoro-2'-hydroxyacetophenone to 4-fluorocatechol without the accumulation of 4'-fluorophenyl acetates. In contrast to 4-fluorophenol, 4-fluorocatechol was further degraded as evidenced by the formation of stoichiometric amounts of fluoride anion. Purified HAPMO catalysed the strictly NADPH-dependent conversion of fluorinated acetophenones to fluorophenyl acetates. Incubations with HAPMO at pH 6 and 8 showed that the enzymatic Baeyer-Villiger oxidation occurred faster at pH 8 but that the phenyl acetates produced were better stabilised at pH 6. Quantum mechanical characteristics explained why 4'-fluoro-2'-hydroxyphenyl acetate was more sensitive to base-catalysed hydrolysis than 4'-fluorophenyl acetate. All together, 19F NMR proved to be a valid method to evaluate the biological conversion of ring-substituted acetophenones to the corresponding phenyl acetates, which can serve as valuable synthons for further production of industrially relevant chemicals. Journal of Industrial Microbiology & Biotechnology (2001) 26, 35-42.
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