title: Synthesis of 8-azidooctyl glycoside derivatives of the O-chain repeating unit of Escherichia coli O9a lipopolysaccharide and a methylated analog.
abstract: Described is the synthesis of 8-azidooctyl glycoside derivatives of the Escherichia coli serotype O9a O-chain tetrasaccharide repeating unit and the terminal tetrasaccharide motif in this polysaccharide, which contains a methyl group on O-3 of the distal mannopyranose residue. The assembly of these compounds involved the sequential addition of monosaccharide residues from the reducing to the nonreducing end of the molecule using glycosyl trichloroacetimidate donors. Both compounds were initially prepared as p-methoxyphenyl glycosides, which were converted to the corresponding 8-azidooctyl derivatives at a late stage in the synthesis.
authors.affiliation: Department of Chemistry and Alberta Ingenuity Centre for Carbohydrate Science, Gunning-Lemieux Chemistry Centre, University of Alberta, Edmonton, AB, Canada.
authors.forename: Dianjie
authors.initials: D
authors.lastname: Hou
authors.forename: Fredrik
authors.initials: F
authors.lastname: Skogman
authors.forename: Todd L
authors.initials: TL
authors.lastname: Lowary
mesh_terms: D001386:Azides / Q000138:chemical synthesis*; D002240:Carbohydrate Sequence; D004926:Escherichia coli / Q000737:chemistry* / Q000276:immunology; D008759:Methylglycosides / Q000138:chemical synthesis*; D019081:O Antigens / Q000737:chemistry*; D009844:Oligosaccharides / Q000138:chemical synthesis*
chemical_list: D001386:Azides; D008759:Methylglycosides; D019081:O Antigens; D009844:Oligosaccharides