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. 2011 Jun 3;13(11):2822-5.
doi: 10.1021/ol200775h. Epub 2011 May 9.

On resin side-chain cyclization of complex peptides using CuAAC

Sampat Ingale  1 , Philip E Dawson
Affiliations

On resin side-chain cyclization of complex peptides using CuAAC

Sampat Ingale et al. Org Lett. .

Abstract

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.

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