SCI和EI收录∣中国化工学会会刊

中国化学工程学报 ›› 2021, Vol. 29 ›› Issue (1): 305-310.DOI: 10.1016/j.cjche.2020.07.014

• Special Topic: Biocatalysis • 上一篇    下一篇

Asymmetric bioreduction of γ- and δ-keto acids by native carbonyl reductases from Saccharomyces cerevisiae

Chunlei Ren1, Tao Wang1, Xiaoyan Zhang1, Jiang Pan1, Jianhe Xu1,2, Yunpeng Bai1,2   

  1. 1 State Key Laboratory of Bioreactor Engineering,;
    2 Shanghai Collaborative Innovation Centre for Biomanufacturing, East China University of Science and Technology, Shanghai 200237, China
  • 收稿日期:2020-01-07 修回日期:2020-06-03 出版日期:2021-01-28 发布日期:2021-04-02
  • 通讯作者: Jianhe Xu, Yunpeng Bai
  • 基金资助:
    This work was financially sponsored by the National Key Research and Development Program of China (2016YFA0204300, 2019YFA09005000), the National Natural Science Foundation of China (21536004, 21776085, 21871085), the Natural Science Foundation of Shanghai (18ZR1409900), Key Project of the Shanghai Science and Technology Committee (18DZ1112703) and the Fundamental Research Funds for the Central Universities (WF1714026).

Asymmetric bioreduction of γ- and δ-keto acids by native carbonyl reductases from Saccharomyces cerevisiae

Chunlei Ren1, Tao Wang1, Xiaoyan Zhang1, Jiang Pan1, Jianhe Xu1,2, Yunpeng Bai1,2   

  1. 1 State Key Laboratory of Bioreactor Engineering,;
    2 Shanghai Collaborative Innovation Centre for Biomanufacturing, East China University of Science and Technology, Shanghai 200237, China
  • Received:2020-01-07 Revised:2020-06-03 Online:2021-01-28 Published:2021-04-02
  • Contact: Jianhe Xu, Yunpeng Bai
  • Supported by:
    This work was financially sponsored by the National Key Research and Development Program of China (2016YFA0204300, 2019YFA09005000), the National Natural Science Foundation of China (21536004, 21776085, 21871085), the Natural Science Foundation of Shanghai (18ZR1409900), Key Project of the Shanghai Science and Technology Committee (18DZ1112703) and the Fundamental Research Funds for the Central Universities (WF1714026).

摘要: Optically pure (R)-γ- and (R)-δ-lactones can be prepared by intramolecular cyclization of chiral hydroxy acids/esters reduced asymmetrically from γ- and δ-keto acids/esters using Saccharomyces cerevisiae (S. cerevisiae) as a whole-cell biocatalyst. However, some of the enzymes catalyzing these reactions in S. cerevisiae are still unknown up to date. In this report, two carbonyl reductases, OdCR1 and OdCR2, were successfully discovered, and cloned from S. cerevisiae using a genome-mining approach, and overexpressed in Escherichia coli (E. coli). Compared with OdCR1, OdCR2 can reduce 4-oxodecanoic acid and 5-oxodecanoic acid asymmetrically with higher stereoselectivity, generating (R)-γ-decalactone (99% ee) and (R)-δ-decalactone (98% ee) in 85% and 92% yields, respectively. This is the first report of native enzymes from S. cerevisiae for the enzymatic synthesis of chiral γ- and δ-lactones which is of wide uses in food and cosmetic industries.

关键词: Keto acids/esters, (R)-γ-/δ-Decalactones, Carbonyl reductase, Asymmetric reduction, Saccharomyces cerevisiae

Abstract: Optically pure (R)-γ- and (R)-δ-lactones can be prepared by intramolecular cyclization of chiral hydroxy acids/esters reduced asymmetrically from γ- and δ-keto acids/esters using Saccharomyces cerevisiae (S. cerevisiae) as a whole-cell biocatalyst. However, some of the enzymes catalyzing these reactions in S. cerevisiae are still unknown up to date. In this report, two carbonyl reductases, OdCR1 and OdCR2, were successfully discovered, and cloned from S. cerevisiae using a genome-mining approach, and overexpressed in Escherichia coli (E. coli). Compared with OdCR1, OdCR2 can reduce 4-oxodecanoic acid and 5-oxodecanoic acid asymmetrically with higher stereoselectivity, generating (R)-γ-decalactone (99% ee) and (R)-δ-decalactone (98% ee) in 85% and 92% yields, respectively. This is the first report of native enzymes from S. cerevisiae for the enzymatic synthesis of chiral γ- and δ-lactones which is of wide uses in food and cosmetic industries.

Key words: Keto acids/esters, (R)-γ-/δ-Decalactones, Carbonyl reductase, Asymmetric reduction, Saccharomyces cerevisiae