title: Chemical synthesis of an artificial antigen containing the trisaccharide hapten of Mycobacterium leprae.
abstract: The trisaccharide allyl O-(3,4-di-O-methyl-beta-D-glucopyranosyl)-(1----4)-O-(2,3-di-O-methyl-al pha-L- rhamnopyranosyl)-(1----2)-3-O-methyl-alpha-L-rhamnopyranoside was synthesized from partially methylated monosaccharide derivatives. Condensation of 1,4-di-O-acetyl-2,3-di-O-methyl-alpha-L-rhamnopyranose promoted by boron trifluoride etherate with the appropriate alcohol proceeded stereoselectively and with very high yields. Selective deacetylation and glycosylation with 2,4-di-O-acetyl-3,6-di-O-methyl-alpha-D-glucopyranosyl bromide led to a trisaccharide. The acrylamide copolymers of mono-, di-, and tri-saccharide were compared in their ability to specifically bind antibodies from leprosy patients.
authors.affiliation: Laboratory for Carbohydrate Chemistry, Facultad de Quimica, Universidad de la Habana, Cuba.
authors.forename: J
authors.initials: J
authors.lastname: Mariño-Albernas
authors.forename: V
authors.initials: V
authors.lastname: Verez-Bencomo
authors.forename: L
authors.initials: L
authors.lastname: Gonzalez-Rodriguez
authors.forename: C S
authors.initials: CS
authors.lastname: Perez-Martinez
authors.forename: E
authors.initials: E
authors.lastname: Gonzalez-Abreu Castell
authors.forename: A
authors.initials: A
authors.lastname: Gonzalez-Segredo
mesh_terms: D000107:Acetylation; D000907:Antibodies, Bacterial / Q000276:immunology; D000942:Antigens, Bacterial; D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D055598:Chemical Phenomena; D002621:Chemistry; D006031:Glycosylation; D006241:Haptens; D006801:Humans; D007918:Leprosy / Q000276:immunology; D008745:Methylation; D008969:Molecular Sequence Data; D015394:Molecular Structure; D009166:Mycobacterium leprae / Q000276:immunology*; D011108:Polymers; D014312:Trisaccharides / Q000138:chemical synthesis*
chemical_list: D000907:Antibodies, Bacterial; D000942:Antigens, Bacterial; D006241:Haptens; D011108:Polymers; D014312:Trisaccharides