Carbasugar Analogues of Galactofuranosides: Pseudodisaccharide Mimics of Fragments of Mycobacterial Arabinogalactan
2011 (English)In: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, no 7, 1367-1375 p.Article in journal (Refereed) Published
A partially protected carbasugar analogue of beta-galactofuranose was converted into an alpha-galacto-configured 1,2-epoxide, which was opened by alcohols under Lewis acid catalysis with regioselective attack at C-1 to give beta-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(beta 1 -> 5) Galf was found to moderately inhibit the action of GlfT2 galactofuranosyl transferase from M. tuberculosis.
Place, publisher, year, edition, pages
2011. no 7, 1367-1375 p.
Carbohydrates, Carbocycles, Pseudodisaccharides, Enzymes, Glycosyl transferases
IdentifiersURN: urn:nbn:se:su:diva-67915DOI: 10.1002/ejoc.201001380ISI: 000288128600020OAI: oai:DiVA.org:su-67915DiVA: diva2:471894
authorCount :42012-01-032012-01-022012-01-03Bibliographically approved