酵母发酵液；不对称还原反应；4氯乙酰乙酸乙酯；(S)4

酵母发酵液催化不对称还原反应合成(S)4氯3羟基丁酸乙酯的条件优化

http://www.100md.com 《第四军医大学学报》 2006年第17期

酵母发酵液；不对称还原反应；4氯乙酰乙酸乙酯；(S)4氯3羟基丁酸乙酯；正交实验,,酵母发酵液；不对称还原反应；4氯乙酰乙酸乙酯；(S)4氯3羟基丁酸乙酯；正交实验,酵母

     Optimization for the asymmetric synthesis of (S)ethyl 4chloro3hydroxybutanoate directly catalyzed by yeast fermentation broth

    MA XiaoKui

    College of Life Science, Shaanxi Normal University, Xian 710062, China

    【Abstract】 AIM: To optimize the asymmetric reduction of ethyl 4chloro3oxobutanoate (COBE) to (S)ethyl 4chloro3hydroxybutanoate [(S)CHBE] directly catalyzed by yeast (Saccharomyces cerevisiae) fermentation broth. METHODS: The variation of COBE, (S)CHBE and reductive sugar in reaction course and the influence of some reaction conditions (substrate, energy source) on asymmetric synthesis of (S)CHBE directly catalyzed by yeast fermentation broth were examined respectively, and the optimal conditions of asymmetric synthesis of (S)CHBE were optimized by orthogonal test design. RESULTS：The consumption of substrate and formation of product were mostly in the initial reaction course as well as consumption of reductive sugar. Repeated feeding strategy of substrate and energy source was favored for the formation of (S)CHBE. The optimum reaction conditions were sucrose repeated feeding strategy Ⅱ (feeding 5 g/120 mL after 2 h of reaction), substrate feeding strategy Ⅳ[0.5(3)], buffer concentration 2 g/120 mL, βcyclodextrin concentration 2 g/120 mL. CONCLUSION: Optically active (S)CHBE is synthesized by yeast fermentation broth with 96% yield and 100% ee (enantiometric excess) under the optimum reaction conditions. ......

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