Carbasugar Analogues of Galactofuranose: Pseudodisaccharide Mimics of Fragments of Mycobacterial Arabinogalactan
(English)Manuscript (preprint) (Other academic)
A partially protected carbasugar analogue of β-galactofuranose was converted into an α-galacto configured 1,2-epoxide, which was was opened by alcohols under Lewis acid catalysis with regioselective attack at C-1 to give β-galacto configured C-1 ethers. Using OH-5 and OH-6 carbagalactofuranose derivatives as nucleophiles, we synthesised pseudodisaccharide analogues of substructures of the arabinogalactan from M. tuberculosis. The dicarba analogue of the disaccharide Galf(β1→5)Galf was found to moderately inhibit the action of GlfT2 galactofuranosyl transferase from M. tuberculosis.
mycobacterial, Glft2, carbasugar, galactofuranose, galactofuranoside, pseudodisaccharide
Organic Chemistry Organic Chemistry
Research subject Organic Chemistry
IdentifiersURN: urn:nbn:se:su:diva-44210OAI: oai:DiVA.org:su-44210DiVA: diva2:360312