Native Chemical Ligation at Valine: A Contribution to Peptide and Glycopeptide Synthesis

被引：170

作者：

Chen, Jin ^{[2
]}

Wan, Qian ^{[2
]}

Yuan, Yu ^{[2
]}

Zhu, Jianglong ^{[2
]}

Danishefsky, Samuel J. ^{[1
,2
]}

机构：

[1] Columbia Univ, Dept Chem, New York, NY 10027 USA

[2] Sloan Kettering Inst Canc Res, Bioorgan Chem Lab, New York, NY 10065 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2008年 / 47卷 / 44期

关键词：

desulfurization; glycopeptides; native chemical ligation; peptides; valine;

D O I：

10.1002/anie.200803523

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) A Val-uable link: The title transformation is achieved by a two-step ligation, radicalbased desulfurization strategy (see scheme; NCL=native chemical ligation). After S→N acyl transfer, in which the acyl acceptor is a γ-thiol valine derivative, and site-specific dethiolation, a valine residue appears at the site of ligation. This method accomplishes ligations at Thr-Val and Pro-Val sites, and allows successful ligation of glycopeptide fragments. © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：8521 / 8524

页数：4

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