Asymmetric Synthesis of N-Substituted α-Amino Esters from α-Ketoesters via Imine Reductase-Catalyzed Reductive Amination

被引：38

作者：

Yao, Peiyuan ^{[1
,2
,3
]}

Marshall, James R. ^{[1
]}

Xu, Zefei ^{[2
,3
]}

Lim, Jesmine ^{[4
]}

Charnock, Simon J. ^{[4
]}

Zhu, Dunming ^{[2
,3
]}

Turner, Nicholas J. ^{[1
]}

机构：

[1] Univ Manchester, Manchester Inst Biotechnol, Dept Chem, 131 Princess St, Manchester M1 7DN, Lancs, England

[2] Chinese Acad Sci, Tianjin Inst Ind Biotechnol, Natl Engn Lab Ind Enzymes, Natl Technol Innovat Ctr Synthet Biol, 32 Xi Qi Dao, Tianjin 300308, Peoples R China

[3] Chinese Acad Sci, Tianjin Inst Ind Biotechnol, Tianjin Engn Res Ctr Biocatalyt Technol, 32 Xi Qi Dao, Tianjin 300308, Peoples R China

[4] Prozomix Ltd, Bldg 4,West End Ind Estate, Haltwhistle NE49 9HA, England

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2021年 / 60卷 / 16期

基金：

国家重点研发计划; 欧洲研究理事会; 英国生物技术与生命科学研究理事会;

关键词：

biocatalysis; chiral amines; imine reductase; reductive amination; α -amino acid;

D O I：

10.1002/anie.202016589

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

N-Substituted alpha-amino esters are widely used as chiral intermediates in a range of pharmaceuticals. Here we report the enantioselective biocatalyic synthesis of N-substituted alpha-amino esters through the direct reductive coupling of alpha-ketoesters and amines employing sequence diverse metagenomic imine reductases (IREDs). Both enantiomers of N-substituted alpha-amino esters were obtained with high conversion and excellent enantioselectivity under mild reaction conditions. In addition >20 different preparative scale transformations were performed highlighting the scalability of this system.

引用

页码：8717 / 8721

页数：5

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