Carbasugar Analogues of Galactofuranosides: Pseudodisaccharide Mimics of Fragments of Mycobacterial Arabino­galactan

Abstract

AbstractA partially protected carbasugar analogue of β‐galactofuranose was converted into an α‐galacto‐configured 1,2‐epoxide, which 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.