Synthesis of the Tetrasaccharide Repeating Unit of the β-Kdo-Containing Exopolysaccharide from Burkholderia pseudomallei and B. cepacia Complex

Anaïs Laroussarie; Barbara Barycza; Hanitra Andriamboavonjy; Marielle Tamigney Kenfack; Yves Blériot; Charles Gauthier

doi:10.1021/acs.joc.5b01823

Synthesis of the Tetrasaccharide Repeating Unit of the β-Kdo-Containing Exopolysaccharide from Burkholderia pseudomallei and B. cepacia Complex

J Org Chem. 2015 Oct 16;80(20):10386-96. doi: 10.1021/acs.joc.5b01823. Epub 2015 Sep 29.

Authors

Anaïs Laroussarie¹, Barbara Barycza^{1

2}, Hanitra Andriamboavonjy¹, Marielle Tamigney Kenfack¹, Yves Blériot¹, Charles Gauthier¹

Affiliations

¹ Université de Poitiers , Institut de Chimie IC2MP, CNRS-UMR 7285, Équipe Synthèse Organique, 4 rue Michel Brunet, 86073 Poitiers Cedex 9, France.
² Department of Chemistry, Wroclaw University of Environmental and Life Sciences , Norwida 25, 50-375 Wroclaw, Poland.

PMID: 26375291
DOI: 10.1021/acs.joc.5b01823

Abstract

The synthesis of the repeating unit of the immunogenic β-Kdo-containing exopolysaccharide produced by Burkholderia pseudomallei and bacteria of the B. cepacia complex is described. The target tetrasaccharide was synthesized via stereoselective 1,2-cis- and 1,2-trans-galactosylations and β-Kdosylation. A [3 + 1] coupling reaction between a trigalactosyl N-phenyl-2,2,2-trifluoroacetimidate donor and a Kdo acceptor has been successfully achieved for the assembly of the tetrasaccharide skeleton.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Burkholderia cepacia / chemistry*
Burkholderia pseudomallei / chemistry*
Galactose / analogs & derivatives
Galactose / chemistry
Molecular Structure
Oligosaccharides / chemical synthesis*
Oligosaccharides / chemistry
Oxidation-Reduction
Stereoisomerism
Sugar Acids / chemistry*

Substances

Oligosaccharides
Sugar Acids
trigalactosyl N-phenyl-2,2,2-trifluoroacetimidate
3-deoxy-beta-manno-2-octulosonic acid thioglycoside
Galactose