Synthesis of water-soluble scaffolds for peptide cyclization, labeling, and ligation

…, H Hiemstra, JH van Maarseveen, P Timmerman

Index: Smeenk, Linde E. J.; Dailly, Nicolas; Hiemstra, Henk; Van Maarseveen, Jan H.; Timmerman, Peter Organic Letters, 2012 , vol. 14, # 5 p. 1194 - 1197

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Citation Number: 25

Abstract

The synthesis and applications of water-soluble scaffolds that conformationally constrain side chain unprotected linear peptides containing two cysteines are described. These scaffolds contain a functionality with orthogonal reactivity to be used for labeling and ligation. This is illustrated by the chemical ligation of two dissimilar constrained peptides via oxime ligation or strain-promoted azide–alkyne cycloaddition in aqueous media.

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