En route to a carbohydrate-based vaccine against Burkholderia cepacia - INSA Toulouse - Institut National des Sciences Appliquées de Toulouse Access content directly
Journal Articles Organic & Biomolecular Chemistry Year : 2007

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 vaccin

Dates and versions

hal-02146194 , version 1 (03-06-2019)

Identifiers

Cite

Régis Fauré, Tze Chieh Shiao, David Lagnoux, Denis Giguère, René Roy. En route to a carbohydrate-based vaccine against Burkholderia cepacia. Organic & Biomolecular Chemistry, 2007, 5 (16), pp.2704. ⟨10.1039/B708365C⟩. ⟨hal-02146194⟩

Collections

INSA-TOULOUSE
15 View
0 Download

Altmetric

Share

Gmail Mastodon Facebook X LinkedIn More