title: Preparation of the pentasaccharide hapten of the GPL of Mycobacterium avium serovar 19 by achieving the glycosylation of a tertiary hydroxyl group.
abstract: The chemical synthesis of the glycopeptidolipid-type pentasaccharide hapten of Mycobacterium avium serovar 19 with a trifluoroacetamido spacer at the reducing end is described. The spacer-armed pentasaccharide 31, when conjugated to an immunogenic protein, can be applied to the serodiagnosis of mycobacterial infections. The questionable structure of the penultimate monosaccharide unit was clarified as 6-deoxy-3-C-methyl-2,4-di-O-methyl-L-mannopyranose. The occurrence of the 6-deoxy-3-C-methyl-2,4-di-O-methyl-L-talopyranose could be excluded by the presence of the large H-1'-H-2' coupling constant, which proves the 4C1 (L) conformation as the favoured one.
authors.affiliation: Research Group for Carbohydrates of the Hungarian Academy of Sciences, PO Box 94, H-4010 Debrecen, Hungary.
authors.forename: Anikó
authors.initials: A
authors.lastname: Fekete
authors.forename: Katalin
authors.initials: K
authors.lastname: Gyergyói
authors.forename: Katalin E
authors.initials: KE
authors.lastname: Kövér
authors.forename: István
authors.initials: I
authors.lastname: Bajza
authors.forename: András
authors.initials: A
authors.lastname: Lipták
mesh_terms: D002240:Carbohydrate Sequence; D006017:Glycolipids / Q000138:chemical synthesis*; D006020:Glycopeptides / Q000138:chemical synthesis*; D006031:Glycosylation; D006241:Haptens / Q000737:chemistry*; D008969:Molecular Sequence Data; D009162:Mycobacterium avium / Q000276:immunology*; D019906:Nuclear Magnetic Resonance, Biomolecular; D009844:Oligosaccharides / Q000138:chemical synthesis*
chemical_list: D006017:Glycolipids; D006020:Glycopeptides; D006241:Haptens; D009844:Oligosaccharides