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© Valérie Choumet
Mosquitoes were orally infected with the chikungunya virus. Midguts were dissected at day 5 post-infection, fixed and permeabilised. Virus is shown in red (anti-E2 protein, cyanine 3), the actin network in green (phalloidin 548) and nuclei in blue (DAPI).
Publication : European Journal of Chemistry

Convergent synthesis, NMR and conformational analysis of tetra- and pentasaccharide haptens of the Shigella flexneri 5a O-specific polysaccharide

Scientific Fields
Diseases
Organisms
Applications
Technique

Published in European Journal of Chemistry - 09 Jul 2002

Mulard LA, Clément MJ, Imberty A, Delepierre M

Eur. J. Org. Chem. 2002, 2486-98

Convergent syntheses of the methyl glycosides of the branched pentasaccharide α-L-Rhap-(12)-[α-D-Glcp-(13)]-α-L-Rhap-(13)-α-L-Rhap-(13)-β-D-GlcNAcp [A(E)BCD], featuring the biological repeating unit of the Ospecific polysaccharide of Shigella flexneri serotype 5a, and of a related linear tetrasaccharide (EBCD) are described. The
strategy, based on the trichloroacetimidate methodology, relied on the use of a key EB disaccharide donor and appropriate CD acceptors. The use of an isopropylidene acetal to block OH-4 and OH-6 of residue D was found to be a suitable alternative to the employment of the more commonly used benzylidene acetal. Conformational analysis of EBCD-OMe and A(E)BCD-OMe was based on analysis of 1H and 13C chemical shifts and inter-proton distances data obtained by NMR spectroscopy. The data showed that residue A had no influence on the conformational behaviour of residue E, although these two residues were involved in a 2,3-cis vicinal glycosylation pattern in A(E)BCD-OMe. Comparison of 1H and 13C chemical shifts of the two oligosaccharides with those of their corresponding sequences in the O-specific polysaccharide of S. flexneri 5a showed that the two oligosaccharides presented a distribution of solution conformations similar to that in the O-specific polysaccharide. The conformation of A(E)BCD-OMe was investigated by two approaches: (i) energy minimisation based on ROE-derived distances with the DISCOVER program and (ii) a conformational searching method (the CICADA algorithm interfaced
with MM3 force-field). The minimised conformation obtained by the former approach was in total agreement with the average of the two major families of conformations resulting from the CICADA calculations.