On Resin Side-Chain Cyclization of Complex Peptides Using CuAAC
On Resin Side-Chain Cyclization of Complex Peptides Using CuAAC
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DOI：
10.1021/ol200775h
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发表时间：
2011-06-03
期刊：
影响因子：
5.2
通讯作者：
Dawson, Philip E.
中科院分区：
文献类型：
--
作者：
Ingale, Sampat;Dawson, Philip E.
已经探索了三唑系链用于稳定肽中的二级结构。尽管这种方法很实用，但复杂肽的环化效率仍然是一个重大挑战。一个强大的，对树脂的协议侧链侧链大环化CuAAC的描述。该方案被应用于从HIV-1 gp 41的膜近端外部区域（MPER）合成呈现结合二肽基序的一系列21个氨基酸的螺旋肽。
Triazole tethers have been explored for stabilization of secondary structures in peptides. Despite the utility of this approach, cyclization efficiency in complex peptides remains a significant challenge. A robust, on-resin protocol for side chain to side chain macrocyclization by CuAAC is described. This protocol was applied to the synthesis of a series of 21 amino acid helical peptides presenting a binding dipeptide motif from the membrane proximal external region (MPER) of HIV-1 gp41.