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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 : Carbohydrate research

Synthesis of methyl O-alpha-L-rhamnopyranosyl-(1–>2)-alpha-D-galactopyranosides specifically deoxygenated at position 3, 4, or 6 of the galactose residue

Scientific Fields
Diseases
Organisms
Applications
Technique

Published in Carbohydrate research - 01 Jan 1994

Mulard LA, Kovác P, Glaudemans CP

Link to Pubmed [PMID] – 7511986

Carbohydr. Res. 1994 Jan;251:213-32

The title disaccharides were synthesized by condensation of 2,3,4-tri-O-benzoyl-alpha-L-rhamnopyranosyl bromide with suitably protected, deoxygenated derivatives of methyl alpha-D-galactopyranoside. Deoxygenation was achieved via activation of a protected methyl alpha-D-gluco- or galacto-pyranoside with N,N’-thiocarbonyldiimidazole followed by treatment with tributyltin hydride and azobisisobutyronitrile. At position 3, the deoxygenation was more successful when performed with the tri-O-benzoylated precursor, rather than the tri-O-benzylated one. The corresponding nucleophile was obtained by benzylidenation of the methyl 3-deoxy-alpha-D-xylo-hexopyranoside. The preparation of the glycosyl acceptor deoxygenated at position 4 could be pursued starting from derivatives having either the D-galacto or the D-gluco configuration. The pathway involving the former was found superior.

http://www.ncbi.nlm.nih.gov/pubmed/7511986