Water-driven chemoselective reaction of squarate derivatives with amino acids and peptides

被引：30

作者：

Sejwal, Preeti ^{[1
]}

Han, Yongbin ^{[1
]}

Shah, Akshay ^{[1
]}

Luk, Yan-Yeung ^{[1
]}

机构：

[1] Syracuse Univ, Dept Chem, Syracuse, NY 13244 USA

来源：

ORGANIC LETTERS | 2007年 / 9卷 / 23期

关键词：

D O I：

10.1021/ol702275q

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Here, we report a new class of highly chemoselective reactions between squarate derivatives and the amino acid cysteine or unprotected peptides with a N-terminus cysteine that proceed most efficiently in entirely aqueous solution at neutral pH. Kinetic and structural studies reveal that the presence of hydrogen bonding in water is primarily responsible for both the high yield and fast rate of the reaction.

引用

页码：4897 / 4900

页数：4

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