Efficient Stereoselective Synthesis of Structurally Diverse γ- and δ-Lactones Using an Engineered Carbonyl Reductase

被引：28

作者：

Chen, Meng ^{[1
]}

Zhang, Xiao-Yan ^{[1
]}

Xing, Chen-Guang ^{[2
]}

Zhang, Chao ^{[1
]}

Zheng, Yu-Cong ^{[1
]}

Pan, Jiang ^{[1
]}

Xu, Jian-He ^{[1
]}

Bai, Yun-Peng ^{[1
]}

机构：

[1] East China Univ Sci & Technol, State Key Lab Bioreactor Engn, 130 Meilong Rd, Shanghai 200237, Peoples R China

[2] Xiamen Oamic Biotech Co Ltd, 36 Longmen Rd, Xiamen 361026, Fujian, Peoples R China

来源：

CHEMCATCHEM | 2019年 / 11卷 / 11期

基金：

上海市自然科学基金; 中国国家自然科学基金;

关键词：

Asymmetric reduction; directed evolution; chiral lactones; carbonyl reductase; biocatalysis; ERROR-PRONE PCR; ASYMMETRIC HYDROGENATION; HYDROXY ESTERS; ENANTIOSELECTIVE REDUCTION; KETO ESTERS; ALPHA-KETO; BETA-KETO; IDENTIFICATION; DECALACTONE; CELLS;

D O I：

10.1002/cctc.201900382

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

Structurally diverse gamma- and delta-lactones were efficiently synthesized stereoselectively using an engineered carbonyl reductase from Serratia marcescens (SmCRV4). SmCRV4 exhibited improved activity (up to 500-fold) and thermostability toward 14 gamma-/delta-keto acids and esters, compared with the wild-type enzyme, with 110-fold enhancement in catalytic efficiency (k(cat)/K-m) toward methyl 4-oxodecanoate. The preparative synthesis of alkyl and aromatic gamma- and delta-lactones with 95 %->99 % ee and 78 %-90 % yields was demonstrated. The highest space-time yield, 1175 g L-1 d(-1), was achieved for (R)-gamma-decalactone.

引用

页码：2600 / 2606

页数：7

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