Synthesis of carbohydrate-amino acid conjugates related to the capsular antigen K54 from Escherichia coli O6:K54:H10 and artificial antigens therefrom.
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.
Chernyak AYa
N. D. Zelinsky Institute of Organic Chemistry, Academy of Sciences of the U.S.S.R., Moscow.
Kononov
L O
LO
Kochetkov
N K
NK
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
D000942:Antigens, Bacterial; D004187:Disaccharides; D006001:Glycoconjugates; D011135:Polysaccharides, Bacterial