Synthesis of the 'primer-adaptor' trisaccharide moiety of Escherichia coli O8, O9, and O9a lipopolysaccharide.
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.
Liu
Chunjuan
C
Department of Chemistry and Alberta Ingenuity Centre for Carbohydrate Science, Gunning-Lemieux Chemistry Centre, University of Alberta, Edmonton, Canada AB T6G 2G2.
Skogman
Fredrik
F
Cai
Ye
Y
Lowary
Todd L
TL
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
D019081:O Antigens; D014312:Trisaccharides