Stereoretentive synthesis and chemoselective amide-forming ligations of C-terminal peptide α-ketoacids
Stereoretentive synthesis and chemoselective amide-forming ligations of C-terminal peptide α-ketoacids
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DOI：
10.1021/ja800053t
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发表时间：
2008-04-02
影响因子：
15
通讯作者：
Bode, Jeffrey W.
中科院分区：
文献类型：
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作者：
Ju, Lei;Lippert, Alexander R.;Bode, Jeffrey W.
C-末端肽氰基硫叶立德容易转化为C-末端肽α-酮酸，准备与羟胺进行化学选择性酰胺形成反应。这些容易制备和工作台稳定的叶立德;快速和选择性地氧化与过硫酸氢钾水溶液，而不需要大多数肽侧链的保护和最小的差向异构化。这种方法提供了制备对映体富集的、侧链未保护的α-酮酸的第一种方法
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