Efficient chemoenzymatic synthesis of (2S,3R)-3-hydroxy-3-methylproline, a key fragment in polyoxypeptin A and FR225659

被引：9

作者：

Zhang, Xiao ^{[1
]}

Renata, Hans ^{[1
]}

机构：

[1] Scripps Res Inst, Dept Chem, 130 Scripps Way, Jupiter, FL 33458 USA

来源：

TETRAHEDRON | 2019年 / 75卷 / 24期

基金：

美国国家卫生研究院;

关键词：

Biocatalysis; Depsipeptide; Chemoenzymatic synthesis; Hydroxylation; BIOSYNTHESIS; STREPTOMYCES; PROTEINS;

D O I：

10.1016/j.tet.2019.04.009

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We report an efficient synthesis of protected (2S,3R)-3-hydroxy-3-methylproline that proceeds in three steps with complete stereoselectivity. This route represents a significant improvement over previous approaches to this noncanonical amino acid. Key to this success is the development of a one-pot che-moenzymatic procedure for the preparation of (25,35)-3-methylproline from L-isoleucine. This work lays the foundation for future chemoenzymatic syntheses of polyoxypeptin A and FR225659. (C) 2019 Elsevier Ltd. All rights reserved.

引用

页码：3253 / 3257

页数：5

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