Lipidation of Cysteine or Cysteine-Containing Peptides Using the Thiol-Ene Reaction (CLipPA) (Eur. J. Org. Chem. 15/2016)

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• 作者：Lili Shi and Zhen Yang
• 刊名：European Journal of Organic Chemistry
• 出版年：2016
• 出版时间：May 2016
• 年：2016
• 卷：2016
• 期：15
• 全文大小：2078K
• ISSN：1099-0690

文摘

The cover picture shows the convenient one-step preparation of S-linked lipopeptides by using the Cysteine Lipidation on a Peptide or Amino Acid (CLipPA) technique, which utilises a thiol-ene reaction between a vinyl ester and a cysteine-containing peptide at the N-terminus. Compounds of this type have potential value as immunotherapeutic agents for the treatment of cancer. When the vinyl ester is derived from palmitic acid, the lipopeptide is a ligand for Toll-Like Receptor 2 (TLR2), which occurs on the surface of Antigen Presenting Cells (APCs). On binding to TLR2, a heterodimer with TLR6 is formed, which induces „maturation” of the APC and leads to a series of events including internalisation, processing and presentation of the peptide component by the Major Histocompatability Complex (MTC). A simultaneous release of cytokines activates antigen-specific T-cells, which then proliferate, seek out and destroy cancerous cells expressing the chosen peptide antigen. Details are discussed in the article by M. A. Brimble et al. on p. rg/10.1002/ejoc.201501375" target="_blank" title="Link to external resource: 2608 ff">2608 ff.