Stereoretentive synthesis and chemoselective amide-forming ligations of C-terminal peptide α-ketoacids

被引：59

作者：

Ju, Lei ^{[1
]}

Lippert, Alexander R. ^{[1
]}

Bode, Jeffrey W. ^{[1
]}

机构：

[1] Univ Penn, Dept Chem, Roy & Diana Vagelos Labs, Philadelphia, PA 19104 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2008年 / 130卷 / 13期

关键词：

D O I：

10.1021/ja800053t

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

C-Terminal peptide cyanosulfur ylides are readily converted to C-terminal peptide alpha-ketoacids, poised for chemoselective amide-forming reactions with hydroxylamines. These easily prepared and bench stable ylides; are quickly and selectively oxidized with aqueous Oxone without the need for protection of most peptide side chains and with minimal epimerization. This approach offers the first method for preparing enantiomerically enriched, side chain unprotected alpha-ketoacids

引用

页码：4253 / +

页数：4

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