Synthesis of novel immunologically active tripalmitoyl‐S‐glycerylcysteinyl lipopeptides as useful intermediates for immunogen preparations
- 12 January 1991
- journal article
- Published by Wiley in International Journal of Peptide and Protein Research
- Vol. 37 (1), 46-57
- https://doi.org/10.1111/j.1399-3011.1991.tb00732.x
Abstract
The synthesis and characterization of lipopeptides consisting of the lipoamino acid N-palmitoyl-S-[2,3-bis(palmitoyloxy)-(2RS)-propyl]-[R]-cysteine (Pam,Cys-OH) and different peptide segments and/or spacer molecules is described. Pam,Cys-peptides, which are derived from the immunologically active TV-terminus of bacterial lipoprotein, were obtained either by solution or solid phase peptide synthesis. In particular, the amphiphilic and water-soluble lipohexapeptides Pam3Cys-Ser-(Lys)4 and Pam3Cys-Ser-(Glu)4 proved to be potent macrophage and B-cell activators and non-toxic, non-pyrogenic immune adjuvants in combination with or covalently linked to antigens and haptens.Keywords
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