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Chemoenzymatic resolution of racemic Wieland–Miescher and Hajos–Parrish ketones

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Abstract

Enantiospecific microbial reduction of bicyclic ketones was described. Racemic Wieland–Miescher (1) and Hajos–Parrish (2) ketones were used as substrates. In a 4-h biotransformation of Hajos–Parrish ketone (2) using the strain of Didymosphaeria igniaria an optically pure ketone (R)-2 was obtained, whereas the (S)-2 ketone underwent reduction to (4aS,5S)-4 alcohol with 100% of enantiomeric excess and with over 60% of diastereoisomeric excess. Jones oxidation of the alcohol obtained in the biotransformation gave an optically pure ketone (S)-2. Enzymatic system of Coryneum betulinum reduced the (R)-2 ketone to (4aR,5S)-4 alcohol with a high enantiomerical purity in a 6-day reaction. Wieland-Miescher (1) ketone was transformed by these microorganisms in an analogous way, but the reaction times were longer.

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Authors and Affiliations

  1. Department of Chemistry, Wrocław University of Environmental and Life Sciences, Norwida 25, 50-375, Wrocław, Poland

    Tomasz Janeczko, Jadwiga Dmochowska-Gładysz & Edyta Kostrzewa-Susłow

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  1. Tomasz Janeczko
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  2. Jadwiga Dmochowska-Gładysz
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  3. Edyta Kostrzewa-Susłow
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Correspondence to Tomasz Janeczko.

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Janeczko, T., Dmochowska-Gładysz, J. & Kostrzewa-Susłow, E. Chemoenzymatic resolution of racemic Wieland–Miescher and Hajos–Parrish ketones. World J Microbiol Biotechnol 26, 2047–2051 (2010). https://doi.org/10.1007/s11274-010-0390-y

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