Stereoselective Reduction of α-Keto Ester and α-Keto Amide with Marine Actinomycetes, Salinispora strains, as Novel Biocatalysts

K. Ishihara, H. Nagai, Kazunari Takahashi, M. Nishiyama, N. Nakajima
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引用次数: 8

Abstract

To clarify the potential ability of marine actinomycetes as biocatalysts, the stereoselective reduction of α-keto esters and α-keto amide using Salinispora arenicola and Salinispora tropica was tested. The reduction of ethyl pyruvate and ethyl 2-oxobutanoate by S. tropica gave corresponding alcohol with high conversion ratio and in high e.e. (96% e.e. (S) and 99% e.e. (S), respectively). In the presence of l-glutamate as an additive, the reduction of ethyl pyruvate by S. tropica afforded the corresponding (S)-ethyl lactate with >99% e.e. Furthermore, 2-chlorobenzoylformamide was reduced by S. tropica to the corresponding (R)-2-chloromandelamide with high conversion ratio and excellent enantioselectivity (>99% e.e.). Thus, it was found that marine actinomycetes, Salinispora strains, had high ability for the stereoselective reduction of carbonyl compounds as useful biocatalysts.
新型生物催化剂海洋放线菌对α-酮酯和α-酮酰胺的立体选择性还原
为了明确海洋放线菌作为生物催化剂的潜在能力,以沙芽孢盐和热带盐为原料对α-酮酯和α-酮酰胺进行了立体选择性还原实验。热带葡萄对丙酮酸乙酯和2-氧丁酸乙酯的还原得到了高转化率和高e - e (96% e - e (S)和99% e - e (S))的相应醇。在l-谷氨酸作为添加剂存在的情况下,热带葡萄球菌还原丙酮酸乙酯得到相应的(S)-乳酸乙酯,e.e为> - 99%,2-氯苯甲酰甲酰胺被热带葡萄球菌还原为相应的(R)-2-氯曼酰胺,转化率高,对映选择性好(> - 99% e.e)。因此,我们发现海洋放线菌Salinispora菌株具有很高的立体选择性还原羰基化合物的能力,是一种有用的生物催化剂。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
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Biochemistry Insights
Biochemistry Insights BIOCHEMISTRY & MOLECULAR BIOLOGY-
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