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

›› 2009, Vol. 17 ›› Issue (3): 493-499.

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

肖美添^1,2, 叶静², 张亚武², 黄雅燕²

1. Institute of Pharmaceutical Engineering, Huaqiao University, Xiamen 361021, China;
2. Department of Chemical and Pharmaceutical Engineering, Huaqiao University, Xiamen 361021, China

收稿日期:2008-09-23 修回日期:2009-03-17 出版日期:2009-06-28 发布日期:2009-06-28
通讯作者: XIAO Meitian,E-mail:mtxiao@hqu.edu.cn
基金资助:
Supported by the Key Project of Science and Technology of Fujian Province (2008N0120);the Key Discipline of Biochemical Engineering of Fujian Province (Huaqiao University)

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

XIAO Meitian^1,2, YE Jing², ZHANG Yawu², HUANG Yayan²

1. Institute of Pharmaceutical Engineering, Huaqiao University, Xiamen 361021, China;
2. Department of Chemical and Pharmaceutical Engineering, Huaqiao University, Xiamen 361021, China

Received:2008-09-23 Revised:2009-03-17 Online:2009-06-28 Published:2009-06-28
Supported by:
Supported by the Key Project of Science and Technology of Fujian Province (2008N0120);the Key Discipline of Biochemical Engineering of Fujian Province (Huaqiao University)

摘要/Abstract

摘要： Baker’s yeast number 6 was selected by screening. It showed good catalytic activity and enantioselectivity 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 reduced 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℃, 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.

关键词: baker’s yeast, asymmetric reduction, (2S,5S)-2,5-hexanediol, enantioselectivity, (SS)-5-hydroxyhexane-2-one

Abstract: Baker’s yeast number 6 was selected by screening. It showed good catalytic activity and enantioselectivity 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 reduced 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℃, 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.

Key words: baker’s yeast, asymmetric reduction, (2S,5S)-2,5-hexanediol, enantioselectivity, (SS)-5-hydroxyhexane-2-one

肖美添, 叶静, 张亚武, 黄雅燕. Reaction Characteristics of Asymmetric Synthesis of (2S,5S)-2,5-Hexanediol Catalyzed with Baker’s Yeast Number 6[J]. , 2009, 17(3): 493-499.

XIAO Meitian, YE Jing, ZHANG Yawu, HUANG Yayan. Reaction Characteristics of Asymmetric Synthesis of (2S,5S)-2,5-Hexanediol Catalyzed with Baker’s Yeast Number 6[J]. , 2009, 17(3): 493-499.

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

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

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