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α-氯-β-酮酯的立体选择性生物催化还原反应

Stereoselective, biocatalytic reductions of alpha-chloro-beta-keto esters.

作者信息

Kaluzna Iwona A, Feske Brent D, Wittayanan Weerawut, Ghiviriga Ion, Stewart Jon D

机构信息

Department of Chemistry, University of Florida, Gainesville, Florida 32611, USA.

出版信息

J Org Chem. 2005 Jan 7;70(1):342-5. doi: 10.1021/jo0484981.

DOI:10.1021/jo0484981
PMID:15624945
Abstract

Eighteen known and putative reductases from baker's yeast (Saccharomyces cerevisiae) were tested for the ability to reduce a series of alpha-chloro-beta-keto esters. In nearly all cases, it was possible to produce at least two of the four possible alpha-chloro-beta-hydroxy ester diastereomers with high optical purities. The utility of this approach was demonstrated by reducing ethyl 2-chloroacetoacetate to the corresponding syn-(2R,3S)-alcohol on a multigram scale using whole cells of an Escherichia coli strain overexpressing a single yeast reductase identified from the screening studies.

摘要

对来自面包酵母(酿酒酵母)的18种已知和推测的还原酶进行了测试,以考察它们还原一系列α-氯-β-酮酯的能力。在几乎所有情况下,都有可能以高光学纯度生成四种可能的α-氯-β-羟基酯非对映异构体中的至少两种。通过使用从筛选研究中鉴定出的一种单一酵母还原酶的过表达大肠杆菌菌株的全细胞,将2-氯乙酰乙酸乙酯以多克规模还原为相应的顺式-(2R,3S)-醇,证明了该方法的实用性。

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