title: Synthesis of allyl glycosides for conversion into neoglycoproteins bearing epitopes of mycobacterial glycolipid antigens.
abstract: Neoglycoproteins bearing key glycosyl substituents of several glycopeptidolipid antigens of pathogenic Mycobacterium species have been synthesized. Allyl glycosides of the terminal 6-deoxyhexose-containing units of the antigens were prepared, with appropriate ether and ester substituents in place. Ozonolysis of the allyl glycosides was then followed by reductive coupling with epsilon-amino groups of lysine residues in bovine serum albumin, using sodium cyanoborohydride at pH 7.8. The resulting neoglycoproteins emulated the antigenicity of the native molecule in several serological tests.
authors.affiliation: Department of Chemistry, York University, Toronto, Ontario, Canada.
authors.forename: G O
authors.initials: GO
authors.lastname: Aspinall
authors.forename: A M
authors.initials: AM
authors.lastname: Crane
authors.forename: D W
authors.initials: DW
authors.lastname: Gammon
authors.forename: I H
authors.initials: IH
authors.lastname: Ibrahim
authors.forename: N K
authors.initials: NK
authors.lastname: Khare
authors.forename: D
authors.initials: D
authors.lastname: Chatterjee
authors.forename: B
authors.initials: B
authors.lastname: Rivoire
authors.forename: P J
authors.initials: PJ
authors.lastname: Brennan
mesh_terms: D000942:Antigens, Bacterial / Q000737:chemistry*; D002240:Carbohydrate Sequence; D000939:Epitopes / Q000737:chemistry; D006017:Glycolipids / Q000737:chemistry / Q000276:immunology; D006023:Glycoproteins / Q000138:chemical synthesis* / Q000737:chemistry / Q000276:immunology*; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry; D008969:Molecular Sequence Data; D015394:Molecular Structure; D015269:Mycobacterium avium Complex / Q000276:immunology
chemical_list: D000942:Antigens, Bacterial; D000939:Epitopes; D006017:Glycolipids; D006023:Glycoproteins; D006027:Glycosides