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近平滑假丝酵母 ATCC 7330 不对称还原 3-氧代丁酸烷基酯:生物催化反应中溶剂和底物优化的见解。

Asymmetric reduction of alkyl-3-oxobutanoates by Candida parapsilosis ATCC 7330: insights into solvent and substrate optimisation of the biocatalytic reaction.

机构信息

Laboratory of Bioorganic Chemistry, Department of Biotechnology, Indian Institute of Technology Madras, Chennai, 600 036, India.

出版信息

Appl Biochem Biotechnol. 2013 Oct;171(3):756-70. doi: 10.1007/s12010-013-0379-8. Epub 2013 Jul 28.

Abstract

Asymmetric reduction of alkyl-3-oxobutanoates mediated by Candida parapsilosis ATCC 7330 resulted in optically pure alkyl-3-hydroxybutanoates in good yields (up to 72%) and excellent enantiomeric excess (up to >99 %). A detailed and systematic optimisation study was necessary and was carried out to avoid the undesired transesterification reaction during the course of asymmetric reduction. Under optimised conditions, the (S)-alkyl hydroxyesters were produced predominantly except for the methyl ester which formed the (R)-enantiomer. To the best of our knowledge, the biocatalytic asymmetric reduction of isoamyl-3-oxobutanoate to (S)-isoamyl-3-hydroxybutanoate is reported here for the first time.

摘要

由近平滑假丝酵母 ATCC 7330 介导的烷基-3-氧代丁酸酯的不对称还原导致光学纯烷基-3-羟基丁酸酯以高收率(高达 72%)和优异的对映体过量(高达>99%)获得。需要进行详细和系统的优化研究,以避免在不对称还原过程中发生不需要的酯交换反应。在优化条件下,主要生成了(S)-烷基羟酯,除了甲酯形成(R)-对映体外。据我们所知,这里首次报道了异戊基-3-氧代丁酸酯的生物催化不对称还原为(S)-异戊基-3-羟基丁酸酯。

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