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. 2010 Apr 16;12(8):1724-7.
doi: 10.1021/ol1003109.

Salicylaldehyde ester-induced chemoselective peptide ligations: enabling generation of natural peptidic linkages at the serine/threonine sites

Xuechen Li  1 , Hiu Yung Lam, Yinfeng Zhang, Chun Kei Chan
Affiliations

Salicylaldehyde ester-induced chemoselective peptide ligations: enabling generation of natural peptidic linkages at the serine/threonine sites

Xuechen Li et al. Org Lett. .

Abstract

A serine/threonine-based chemoselective ligation method is described. It uses an O-salicylaldehyde ester at the C-terminus, reacting with N-terminal serine or threonine to realize peptide ligations. The utility of the O-salicylaldehyde ester enables the rapid coupling reaction and the production of an N,O-benzylidene acetal intermediate, which is readily converted into natural peptidic linkages (Xaa-Ser/Thr) at the ligation site.

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