title: Synthesis of carbohydrate-amino acid conjugates related to the capsular antigen K54 from Escherichia coli O6:K54:H10 and artificial antigens therefrom.
abstract: The disaccharides alpha-L-Rhap-(1----3)-beta-D-GlcpA and beta-D-GlcpA-(1----3)-alpha-L-Rhap bearing amide-linked L-serine or L-threonine, which represent the repeating unit(s) of the capsular polysaccharide from E. coli O6:K54:H10, have been synthesised. O-tert-Butyl-protected amino acid tert-butyl esters were condensed with the corresponding biouronic acid as the 2-acrylamidoethyl or 2-azidoethyl glycosides. The azido function was replaced by the acrylamido group by catalytic hydrogenation followed by N-acryloylation. The tert-butyl groups were removed by treatment with trifluoroacetic acid to give the target monomers which were copolymerised with acrylamide to give neoglycoconjugates that are potentially useful for immunochemical studies.
authors.affiliation: N. D. Zelinsky Institute of Organic Chemistry, Academy of Sciences of the U.S.S.R., Moscow.
authors.lastname: Chernyak AYa
authors.forename: L O
authors.initials: LO
authors.lastname: Kononov
authors.forename: N K
authors.initials: NK
authors.lastname: Kochetkov
mesh_terms: D000942:Antigens, Bacterial / Q000737:chemistry*; D002240:Carbohydrate Sequence; D004187:Disaccharides / Q000138:chemical synthesis / Q000737:chemistry / Q000276:immunology; D004926:Escherichia coli / Q000276:immunology; D006001:Glycoconjugates / Q000138:chemical synthesis* / Q000276:immunology*; D008969:Molecular Sequence Data; D015394:Molecular Structure; D011135:Polysaccharides, Bacterial / Q000737:chemistry* / Q000276:immunology
chemical_list: D000942:Antigens, Bacterial; D004187:Disaccharides; D006001:Glycoconjugates; D011135:Polysaccharides, Bacterial