European Journal of Organic Chemistry
© WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Lipidation of Cysteine or Cysteine-Containing Peptides Using the Thiol-Ene Reaction (CLipPA) (Eur. J. Org. Chem. 15/2016)
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. 2608 ff.