SCI和EI收录∣中国化工学会会刊

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

• BIOTECHNOLOGY AND BIOENGINEERING • Previous Articles     Next Articles

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

XIAO Meitian1,2, YE Jing2, ZHANG Yawu2, HUANG Yayan2   

  1. 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)

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

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

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