The Mercaptomethyl Group Facilitates an Efficient One-Pot Ligation at Xaa-Ser/Thr for (Glyco)peptide Synthesis

被引：32

作者：

Hojo, Hironobu ^{[1
]}

Ozawa, Chinatsu ^{[1
]}

Katayama, Hidekazu ^{[1
]}

Ueki, Akiharu ^{[1
]}

Nakahara, Yuko ^{[1
]}

Nakahara, Yoshiaki ^{[1
]}

机构：

[1] Tokai Univ, Inst Glycosci, Dept Appl Biochem, Kanagawa 2591292, Japan

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2010年 / 49卷 / 31期

基金：

日本学术振兴会;

关键词：

glycopeptides; ligation; peptide thioesters; synthetic methods; NATIVE CHEMICAL LIGATION; GLYCOPEPTIDE LIGATION; THIOESTER METHOD; ASSISTED THIOESTERIFICATION; CYSTEINE; AUXILIARY; PEPTIDES; DESULFURIZATION; PROTEINS; SITE;

D O I：

10.1002/anie.201000384

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Going native: A mercaptomethyl group on the side-chain hydroxy group of serine and threonine residues facilitates a native chemical ligation reaction at the Xaa-Ser/Thr site (see scheme; R=H or Me). The intermediate thioester is treated to achieve an S- to W-acyl shift. After ligation, the group is spontaneously removed to obtain the glycopeptide contulakin-G and human calcitonin. (Figure Presented) © 2010 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：5318 / 5321

页数：4

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