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

doi:10.1016/j.cjche.2020.07.014

Chinese Journal of Chemical Engineering ›› 2021, Vol. 29 ›› Issue (1): 305-310.DOI: 10.1016/j.cjche.2020.07.014

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

Chunlei Ren¹, Tao Wang¹, Xiaoyan Zhang¹, Jiang Pan¹, Jianhe Xu^1,2, Yunpeng Bai^1,2

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:2021-04-02 Published:2021-01-28
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).

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

Chunlei Ren¹, Tao Wang¹, Xiaoyan Zhang¹, Jiang Pan¹, Jianhe Xu^1,2, Yunpeng Bai^1,2

1 State Key Laboratory of Bioreactor Engineering,;
2 Shanghai Collaborative Innovation Centre for Biomanufacturing, East China University of Science and Technology, Shanghai 200237, China

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).

Abstract

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

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

Chunlei Ren, Tao Wang, Xiaoyan Zhang, Jiang Pan, Jianhe Xu, Yunpeng Bai. Asymmetric bioreduction of γ- and δ-keto acids by native carbonyl reductases from Saccharomyces cerevisiae[J]. Chinese Journal of Chemical Engineering, 2021, 29(1): 305-310.

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

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

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