En route to a carbohydrate-based vaccine against Burkholderia cepacia.
We report a very high yielding first total synthesis of trisaccharide 5, alpha-D-Rhap-(1 --> 3)-alpha-D-Rhap-(1 --> 4)-alpha-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 oligosaccharide 5 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.
Fauré
Régis
R
Equipe PharmaQAM, Département de Chimie, Université du Québec a Montréal, P.O. Box 8888, Succ. Centre-Ville, H3C 3P8 Montréal, Québec, Canada.
Shiao
Tze Chieh
TC
Lagnoux
David
D
Giguère
Denis
D
Roy
René
R
D016956:Burkholderia cepacia / Q000276:immunology; D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D002241:Carbohydrates / Q000138:chemical synthesis* / Q000737:chemistry / Q000276:immunology; D011135:Polysaccharides, Bacterial / Q000737:chemistry*; D014312:Trisaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D014612:Vaccines / Q000138:chemical synthesis* / Q000737:chemistry
D002241:Carbohydrates; D011135:Polysaccharides, Bacterial; D014312:Trisaccharides; D014612:Vaccines