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Reaction Characteristics of Asymmetric Synthesis of (2S,5S)-2,5-Hexanediol Catalyzed with Baker’s Yeast Number 6 被引量:2

面包酵母No.6催化不对称合成(2S,5S)-2,5-己二醇反应特性(英文)
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摘要 Baker’s yeast number 6 was selected by screening. It showed good catalytic activity and enantioselec-tivity for asymmetric reduction of 2,5-hexanedione to produce (2S,5S)-2,5-hexanediol. Gas chromatography-mass spectrometry (GC-MS) revealed that the intermediate was (S)-5-hydroxyhexane-2-one. Reduction of 2,5-hexanedione proceeded in a two-step reaction. The hydroxyketone was initially formed, and this intermediate was further re-duced to the diol. Factors influencing the product yield and the enantiomeric excess of the reduction of 2,5-hexandione catalyzed by baker’s yeast number 6 were investigated. Higher concentration (≤100 mmol·L-1) of 2,5-hexandione did not influence 5-hydroxyhexane-2-one production, but 2,5-hexanediol production was inhibited by excess accumulation (>30 mmol·L-1) of intermediate. The optimal conditions were glucose as the co-substrate at an initial glucose concentration of 20 g·L-1, 34°C, pH 7.0 and cell concentration 60 g·L-1 (cell dry mass). Under the optimal condition and an initial substrate concentration of 30 mmol·L-1, the yield of 2,5-hexandiol was 78.7% and the enantiomeric excess of (2S,5S)-2,5-hexandiol was 94.4% for 24-h reduction. Baker’s yeast number 6 was selected by screening. It showed good catalytic activity and enantioselec-tivity for asymmetric reduction of 2,5-hexanedione to produce (2S,5S)-2,5-hexanediol. Gas chromatography-mass spectrometry (GC-MS) revealed that the intermediate was (S)-5-hydroxyhexane-2-one. Reduction of 2,5-hexanedione proceeded in a two-step reaction. The hydroxyketone was initially formed, and this intermediate was further re-duced to the diol. Factors influencing the product yield and the enantiomeric excess of the reduction of 2,5-hexandione catalyzed by baker’s yeast number 6 were investigated. Higher concentration (≤100 mmol·L-1) of 2,5-hexandione did not influence 5-hydroxyhexane-2-one production, but 2,5-hexanediol production was inhibited by excess accumulation (〉30 mmol·L-1) of intermediate. The optimal conditions were glucose as the co-substrate at an initial glucose concentration of 20 g·L-1, 34°C, pH 7.0 and cell concentration 60 g·L-1 (cell dry mass). Under the optimal condition and an initial substrate concentration of 30 mmol·L-1, the yield of 2,5-hexandiol was 78.7% and the enantiomeric excess of (2S,5S)-2,5-hexandiol was 94.4% for 24-h reduction.
出处 《Chinese Journal of Chemical Engineering》 SCIE EI CAS CSCD 2009年第3期493-499,共7页 中国化学工程学报(英文版)
基金 Supported by the Key Project of Science and Technology of Fujian Province (2008N0120) the Key Discipline of Biochemical Engineering of Fujian Province (Huaqiao University)
关键词 baker's yeast asymmetric reduetion (2S 5S)-2 5-hexanediol ENANTIOSELECTIVITY (S)-5-hydroxyhexane-2-one 不对称反应 表征 贝克酵母菌 催化反应 5-羟基己烷-2-酮
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