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Issue 16, 2007
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En route to a carbohydrate-based vaccine against Burkholderia cepacia

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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.

Graphical abstract: En route to a carbohydrate-based vaccine against Burkholderia cepacia

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Article information


Submitted
04 Jun 2007
Accepted
22 Jun 2007
First published
13 Jul 2007

Org. Biomol. Chem., 2007,5, 2704-2708
Article type
Paper

En route to a carbohydrate-based vaccine against Burkholderia cepacia

R. Fauré, T. C. Shiao, D. Lagnoux, D. Giguère and R. Roy, Org. Biomol. Chem., 2007, 5, 2704 DOI: 10.1039/B708365C

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