Synthesis of Thiazolidine Thioester Peptides and Acceleration of Native Chemical Ligation

被引：53

作者：

Dheur, Julien ^{[1
]}

Ollivier, Nathalie ^{[1
]}

Melnyk, Oleg ^{[1
]}

机构：

[1] Univ Lille Nord France, Inst Pasteur, UMR 8161, CNRS,IFR Mol & Cellular Med 142, F-59021 Lille, France

来源：

ORGANIC LETTERS | 2011年 / 13卷 / 06期

关键词：

SOLID-PHASE SYNTHESIS; CPE AUTOACTIVATING UNIT; S ACYL SHIFT; C-TERMINAL THIOESTERS; NUCLEOPHILIC CATALYSIS; SIDE-CHAIN; CYSTEINE; AMIDE; CHEMISTRY; AUXILIARY;

D O I：

10.1021/ol2002804

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Thiazolidine thioester peptides were synthesized by reacting bis(2-sulfanylethyl)amido peptides with glyoxylic acid at pH 1. A significant increase in Native Chemical Ligation (NCL) rate was observed with thiazolidine thioesters compared to 3-mercaptopropionic acid-thioester analogues. The method is of particular interest for accelerating valine-cysteine peptide bond formation.

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页码：1560 / 1563

页数：4

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