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Enantioselective Biocatalytic Reduction of 1-(4-Fluorophenyl)ethanone
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...
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Published in: | Russian journal of general chemistry 2023-12, Vol.93 (13), p.3343-3347 |
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Main Authors: | , , , |
Format: | Article |
Language: | English |
Subjects: | |
Citations: | Items that this one cites |
Online Access: | Get full text |
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Summary: | 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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ISSN: | 1070-3632 1608-3350 |
DOI: | 10.1134/S1070363223130108 |