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Enantioselective Biocatalytic Reduction of 1-(4-Fluorophenyl)ethanone

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Abstract

Enantioselective reduction of 1-(4-fluorophenyl)ethanone, catalyzed by P. crispum cells, was studied. Conditions that allow obtaining (S)-(–)-1-(4-fluorophenyl)ethanol by bioreduction of 1-(4-fluorophenyl)ethanone in the presence of a P. crispum biocatalyst for 48 h with a 46% yield (90% ee) were found. The possibility of optimizing the conditions for the biotransformation of 1-(4-fluorophenyl)ethanone in a reaction medium containing exogenous reducing agents (ethanol, isopropanol, or glucose) was studied. It was revealed that the bioreduction of 1-(4-fluorophenyl)ethanone in the presence of ethanol, isopropanol (1‒5%), or of an equimolar amount of glucose as an exogenous reducing agent mainly leads to the formation of an S-alcohol with moderate yields and optical purities. However, bioreduction of 1-(4-fluorophenyl)ethanone in the presence of 4 and 5% of isopropanol during 144 h leads to the (R)-enantiomer of 1-(4-fluorophenyl)ethanol with the respective yields of 50 and 76% and optical purities of 14 and 20% ee.

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Funding

This work was supported by ongoing institutional funding. No additional grants to carry out or direct thisparticular research were obtained.

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Authors and Affiliations

  1. Ufa State Petroleum Technological University, 450062, Ufa, Russia

    A. R. Chanysheva, S. T. Dibaeva, N. F. Feumo & V. V. Zorin

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  1. A. R. Chanysheva
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  2. S. T. Dibaeva
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  3. N. F. Feumo
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  4. V. V. Zorin
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Correspondence to A. R. Chanysheva.

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Chanysheva, A.R., Dibaeva, S.T., Feumo, N.F. et al. Enantioselective Biocatalytic Reduction of 1-(4-Fluorophenyl)ethanone. Russ J Gen Chem 93, 3343–3347 (2023). https://doi.org/10.1134/S1070363223130108

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