Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2011, Issue 7, Pages 1367-1375Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201001380
Keywords
Carbohydrates; Carbocycles; Pseudodisaccharides; Enzymes; Glycosyl transferases
Categories
Funding
- Swedish Research Council (Vetenskapsradet)
- Carl Tryggers Stiftelse
- Alberta Ingenuity Centre for Carbohydrate Science
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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.
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