Abstract

The immunostimulatory activity of naturally occurring lipopeptides as bacterial cell wall components arises due to the presence of certain lipid motifs. S-[2,3-bis(palmitoyloxy)propyl]cysteine (Pam2Cys) is a lipid motif known to successfully reproduce this immunostimulatory activity when incorporated into synthetic peptides. Herein we report the synthesis of a Pam2Cys analogue designed to facilitate the fully convergent, efficient generation of lipopeptide mimics using click chemistry to effect its ligation to suitably functionalized peptides. The incorporation of this Pam2Cys mimic into peptides prepared by SPPS is also demonstrated.

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