En route to a carbohydrate-based vaccine against Burkholderia cepacia

Abstract

We report a very high yielding first total synthesis of trisaccharide 5, α-D-Rhap-(1→3)-α-D-Rhap-(1→4)-α-D-Galp, corresponding to the repeating unit 1 of an O-polysaccharide present in the lipopolysaccharide of clinical isolate of Burkholderia cepacia. The approach included two successive glycosylations, based on D-rhamnosyl trichloroacetimidate donors 12 and 14. The oligosaccharide5 has been further functionalized by photochemical coupling or cross-metathesis with non-natural amino acid derivatives. Trisaccharidylamino acids 16 and 17 are now available, with the aim of preparing a novel synthetic carbohydrate-based vaccine.