Enantioselective Biocatalytic Reduction of Hexan-2-one, Catalyzed by Petroselinum crispum Cells

A method for the synthesis of (2 S )-(+)-hexan-2-ol, a precursor of a number of drugs, by the enantioselective biocatalytic reduction of a prochiral hexan-2-one, catalyzed by P. crispum cells, is proposed. Conditions for the synthesis of (2 S )-(+)-hexan-2-ol within 48 h in a yield of 98% and an opt...

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Bibliographic Details
Published in:Russian journal of general chemistry 2020-12, Vol.90 (13), p.2542-2545
Main Authors: Chanysheva, A. R., Privalov, N. V., Zorin, V. V.
Format: Article
Language:English
Subjects:
Biotransformation
Chemistry
Chemistry and Materials Science
Chemistry/Food Science
Enantiomers
Ethanol
Isopropanol
Purity
Reduction
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Summary:A method for the synthesis of (2 S )-(+)-hexan-2-ol, a precursor of a number of drugs, by the enantioselective biocatalytic reduction of a prochiral hexan-2-one, catalyzed by P. crispum cells, is proposed. Conditions for the synthesis of (2 S )-(+)-hexan-2-ol within 48 h in a yield of 98% and an optical purity of 99% ee in the presence of isopropanol (3%) and in a yield of 85% and an optical purity of 90% ee in the presence of ethanol (2%) were found. It was shown that when the time of biotransformation in the presence of isopropanol and ethanol was prolonged to 144 h, the yield and optical purity of (2 S )-(+)-hexan-2-ol significantly decrease, and the concentration of the starting ketone increases. With 1% isopropanol and 3 and 4% ethanol, only the starting hexan-2-one was present in the reaction mixture.
ISSN:1070-3632
1608-3350
DOI:10.1134/S1070363220130022