Laboratory of Bioorganic Chemistry, Department of Biotechnology, Indian Institute of Technology Madras, Chennai, 600 036, India.
Appl Biochem Biotechnol. 2013 Oct;171(3):756-70. doi: 10.1007/s12010-013-0379-8. Epub 2013 Jul 28.
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.
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。