title: Synthesis of a new template with a built-in adjuvant and its use in constructing peptide vaccine candidates through polyoxime chemistry.
abstract: 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.
authors.affiliation: CMU, Geneva, Switzerland.
authors.forename: W
authors.initials: W
authors.lastname: Zeng
authors.forename: D C
authors.initials: DC
authors.lastname: Jackson
authors.forename: K
authors.initials: K
authors.lastname: Rose
mesh_terms: 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*
chemical_list: 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