Synthesis of novel immunologically active tripalmitoyl-S-glycerylcysteinyl lipopeptides as useful intermediates for immunogen preparations

Int J Pept Protein Res. 1991 Jan;37(1):46-57. doi: 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 (Pam3Cys-OH) and different peptide segments and/or spacer molecules is described. Pam3Cys-peptides, which are derived from the immunologically active N-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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Adjuvants, Immunologic / chemical synthesis*
  • Amino Acid Sequence
  • Animals
  • Cysteine / analogs & derivatives*
  • Cysteine / chemical synthesis
  • Cysteine / immunology
  • Cysteine / pharmacology
  • In Vitro Techniques
  • Lipoproteins / chemical synthesis*
  • Lipoproteins / immunology
  • Lipoproteins / pharmacology
  • Lymphocyte Activation
  • Macrophage Activation
  • Mice
  • Molecular Sequence Data
  • Structure-Activity Relationship

Substances

  • Adjuvants, Immunologic
  • Lipoproteins
  • 2,3-bis(palmitoyloxy)-2-propyl-1-palmitoylcysteine
  • Cysteine