Synthesis of 5-O-oligoglucosyl extended α-(2→4)-Kdo disaccharides corresponding to inner core fragments of Moraxellaceae lipopolysaccharides.

The heptose-deficient inner core of the lipopolysaccharide of several pathogenic strains of the Moraxellaceae family (Moraxella, Acinetobacter) and of Bartonella henselae, respectively, comprises an α-D-glucopyranose attached to position 5 of Kdo. In continuation of the synthesis of fragments of Acinetobacter haemolyticus LPS, the branched α-Glcp-(1 → 5)[α-Kdo-(2 → 4)]-α-Kdo trisaccharide motif was elaborated. The glycosylation of a suitably protected, α-(2 → 4)-interlinked Kdo-disaccharide was achieved in high yield and fair anomeric selectivity using a 4,6-O-benzylidene N-phenyltrifluoroacetimidate glucosyl donor. Subsequent regioselective reductive benzylidene opening afforded a trisaccharide acceptor, which was extended with β-D-glucopyranosyl and isomaltosyl residues. Global deprotection provided tri- to pentasaccharide structures corresponding to the inner core region of A. haemolyticus lipopolysaccharide.