Synthesis of a novel pentasaccharide core component from the lipooligosaccharide of Moraxella catarrhalis

Abstract

The novel pentasaccharide [p-(trifluoroacetamido)phenyl]ethyl 3-O-b-D-glucopyranosyl-4-O-b-D-glucopyranosyl-6-O-[2-O-(a-D-glucopyranosyl)-b-D-glucopyranosyl]-a-D-glucopyranoside (1), which includes a linker moiety to enable facile coupling to an antigenic protein, was synthesised as a component of a potential vaccine candidate against the Gram-negative bacterium Moraxella catarrhalis. This microorganism is one of three principal causative agents of otitis media in children. The pentasaccharide represents a common cross-serotype (A, B and C) structure from the lipooligosaccharides of Moraxella catarrhalis.