Loading…

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...

Full description

Saved in:
Bibliographic Details
Published in:Russian journal of general chemistry 2023-12, Vol.93 (13), p.3343-3347
Main Authors: Chanysheva, A. R., Dibaeva, S. T., Feumo, N. F., Zorin, V. V.
Format: Article
Language:English
Subjects:
Citations: Items that this one cites
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
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.
ISSN:1070-3632
1608-3350
DOI:10.1134/S1070363223130108