title: Synthesis of the 'primer-adaptor' trisaccharide moiety of Escherichia coli O8, O9, and O9a lipopolysaccharide.
abstract: Described is the synthesis of the trisaccharide alpha-D-Manp-(1-->3)-alpha-D-Manp-(1-->3)-beta-D-GlcpNAcO(CH2)8N3, the glycan portion of which corresponds to the 'adaptor-primer' moiety linking the O-chain and core oligosaccharide in the lipopolysaccharide of several Escherichia coli and Klebsiella pneumoniae serotypes. This report represents the first synthesis of this trisaccharide motif, and in the route involved, a key step is a [2+1] coupling of a protected Manp-(1-->3)-alpha-D-Manp glycosyl donor with a GlcpNAc acceptor. The azido group was included in the target to facilitate future preparation of neoglycoconjugates.
authors: Department of Chemistry and Alberta Ingenuity Centre for Carbohydrate Science, Gunning-Lemieux Chemistry Centre, University of Alberta, Edmonton, Canada AB T6G 2G2.
authors: Chunjuan
authors: C
authors: Liu
authors: Fredrik
authors: F
authors: Skogman
authors: Ye
authors: Y
authors: Cai
authors: Todd L
authors: TL
authors: Lowary
mesh_terms: D002240:Carbohydrate Sequence; D004926:Escherichia coli / Q000737:chemistry*; D007711:Klebsiella pneumoniae / Q000737:chemistry; D008969:Molecular Sequence Data; D019081:O Antigens / Q000737:chemistry*; D014312:Trisaccharides / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D019081:O Antigens; D014312:Trisaccharides