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

TETRAHEDRON

卷:75

Article

Zhang, Xiao¹  Renata, Hans¹ 

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

关键词: Biocatalysis;    Depsipeptide;    Chemoenzymatic synthesis;    Hydroxylation;   

DOI  :  10.1016/j.tet.2019.04.009

来源: Elsevier

【 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.

【 授权许可】

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