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

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journal contribution
posted on 16.10.2015, 00:00 by Anaïs Laroussarie, Barbara Barycza, Hanitra Andriamboavonjy, Marielle Tamigney Kenfack, Yves Blériot, Charles Gauthier
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.