An Improved Method for the Synthesis of Lipopeptide TLR2-Agonists Using Click Chemistry

作者：Wright Tom H; Brooks Anna E S; Did**ury Alicia J; McIntosh Julie D; Burkert Kristina; Yeung Ho; Williams Geoffrey M; Dunbar P Rod; Brimble Margaret A^*

来源：Synlett, 2013, 24(14): 1835-1841.

DOI：10.1055/s-0033-1339349

• lipopeptides
• CuAAC
• synthetic lipids
• adjuvant
• click chemistry

S-[2,3-Bis(palmitoyloxy)propyl]cysteine (Pam(2)Cys) is a synthetic lipid motif known to act as a TLR2 agonist when incorporated into peptide vaccines. Herein, we report the synthesis of Pam(2)Cys-containing, propargyl-functionalised 'clickable' building blocks and their conjugation with azide-functionalised antigenic peptides using click chemistry. This method facilitates the fully convergent preparation of self-adjuvanting lipopeptides for use as vaccines.

• 出版日期2013-9