Click chemistry as a macrocyclization tool in the solid-phase synthesis of small cyclic peptides

被引:135
|
作者
Turner, Rushia A. [1 ]
Oliver, Allen G. [1 ]
Lokey, R. Scott [1 ]
机构
[1] Univ Calif Santa Cruz, Dept Chem & Biochem, Santa Cruz, CA 95064 USA
关键词
D O I
10.1021/ol702228u
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Despite the vast number of techniques developed for the cyclization of small peptides, cyclization efficiency remains problematic in peptides that lack turn-promoting structures. Here we demonstrate the utility of click chemistry as a macrocyclization tool in the solid-phase synthesis of cyclic tetra-, penta-, hexa-, and heptapeptides. On-resin cyclization is completed at room temperature within 6 h, resulting in predominantly monomer with small amounts of cyclomultimer byproducts.
引用
收藏
页码:5011 / 5014
页数:4
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