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.

中文翻译：

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1-(4-氟苯基)乙酮的对映选择性生物催化还原

摘要

研究了卷曲青霉细胞催化的 1-(4-氟苯基)乙酮的对映选择性还原。允许通过在卷花生物催化剂存在下生物还原 1-(4-氟苯基)乙酮48 小时获得 ( S )-(–)-1-(4-氟苯基)乙醇的条件，产率 46% (90 % ee) 被发现。研究了在含有外源还原剂（乙醇、异丙醇或葡萄糖）的反应介质中优化 1-(4-氟苯基)乙酮生物转化条件的可能性。研究表明，在乙醇、异丙醇（1-5%）或等摩尔量的葡萄糖作为外源还原剂存在下，1-(4-氟苯基)乙酮的生物还原主要导致S-的形成。具有中等收率和光学纯度的酒精。然而，在 4% 和 5% 异丙醇存在下，1-(4-氟苯基)乙酮在 144 小时内生物还原，得到 1-(4-氟苯基)乙醇的 ( R )-对映体，产率分别为 50 和 76 % 和光学纯度分别为 14% 和 20% ee。