Synthesis of novel immunologically active tripalmitoyl-S-glycerylcysteinyl lipopeptides as useful intermediates for immunogen preparations.
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.
Metzger
J
J
Institute for Organic Chemistry, University of Tübingen, FRG.
Wiesmüller
K H
KH
Schaude
R
R
Bessler
W G
WG
Jung
G
G
D000276:Adjuvants, Immunologic / Q000138:chemical synthesis*; D000595:Amino Acid Sequence; D000818:Animals; D003545:Cysteine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000276:immunology / Q000494:pharmacology; D066298:In Vitro Techniques; D008074:Lipoproteins / Q000138:chemical synthesis* / Q000276:immunology / Q000494:pharmacology; D008213:Lymphocyte Activation; D008262:Macrophage Activation; D051379:Mice; D008969:Molecular Sequence Data; D013329:Structure-Activity Relationship
D000276:Adjuvants, Immunologic; D008074:Lipoproteins; C069172:2,3-bis(palmitoyloxy)-2-propyl-1-palmitoylcysteine; D003545:Cysteine