Synthesis of a new template with a built-in adjuvant and its use in constructing peptide vaccine candidates through polyoxime chemistry.
Synthetic lipopeptides are showing promise as vaccine candidates, but until now it has been very difficult to prepare them in homogeneous form. We describe the synthesis and characterization of a new water-soluble, four-branched template with a built-in lipophilic adjuvant (Pam3Cys). Through the use of oxime chemistry, we attached four copies of an unprotected influenza virus peptide and characterized the product (13 kDa) by reversed-phase HPLC and electrospray ionization mass spectrometry. Several other such constructions were made using the new template and different peptides. We seem to have a general method for making synthetic lipopeptides in homogeneous form.
Zeng
W
W
CMU, Geneva, Switzerland.
Jackson
D C
DC
Rose
K
K
D000276:Adjuvants, Immunologic / Q000378:metabolism*; D000595:Amino Acid Sequence; D001383:Azetidinecarboxylic Acid / Q000031:analogs & derivatives*; D002851:Chromatography, High Pressure Liquid; D003545:Cysteine / Q000031:analogs & derivatives* / Q000378:metabolism; D007252:Influenza Vaccines / Q000138:chemical synthesis*; D008074:Lipoproteins / Q000378:metabolism*; D013058:Mass Spectrometry; D008969:Molecular Sequence Data; D008970:Molecular Weight; D009975:Orthomyxoviridae; D011487:Protein Conformation; D013698:Templates, Genetic; D014614:Vaccines, Synthetic; D014764:Viral Proteins / Q000276:immunology*
D000276:Adjuvants, Immunologic; D007252:Influenza Vaccines; D008074:Lipoproteins; D014614:Vaccines, Synthetic; D014764:Viral Proteins; C010624:polyoximic acid; D001383:Azetidinecarboxylic Acid; C069172:2,3-bis(palmitoyloxy)-2-propyl-1-palmitoylcysteine; D003545:Cysteine