title: S-linked ganglioside analogues for use in conjugate vaccines.
abstract: [structure: see text] Glycosidase resistant thioglycoside precursors of the melanoma-associated ganglioside GM(2) have been synthesized starting from lactose. Syntheses of several analogues of ganglioside GM(3) and a positional isomer have been developed. These compounds contain thio-linked sialic acid residues and a modified ceramide aglycon functionalized for coupling to proteins, surfaces, or matrices. The hydrolytic stability of these oligosaccharides enhances the immunogenicity of the corresponding conjugate vaccines by ensuring their integrity in the acidic compartments of antigen processing cells.
authors.affiliation: Alberta Ingenuity Centre for Carbohydrate Science, Department of Chemistry, University of Alberta, Edmonton, AB T6G 2G2, Canada. jrich@ualberta.ca
authors.forename: Jamie R
authors.initials: JR
authors.lastname: Rich
authors.forename: David R
authors.initials: DR
authors.lastname: Bundle
mesh_terms: D000917:Antibody Formation; D000954:Antigens, Surface / Q000737:chemistry; D003429:Cross Reactions; D005732:Gangliosides / Q000138:chemical synthesis* / Q000276:immunology / Q000627:therapeutic use; D008545:Melanoma / Q000276:immunology / Q000628:therapy; D015394:Molecular Structure; D013865:Thioglycosides / Q000737:chemistry*; D014312:Trisaccharides / Q000737:chemistry / Q000276:immunology; D018074:Vaccines, Conjugate / Q000276:immunology / Q000627:therapeutic use
chemical_list: D000954:Antigens, Surface; D005732:Gangliosides; D013865:Thioglycosides; D014312:Trisaccharides; D018074:Vaccines, Conjugate