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

A 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 derivativ...

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Bibliographic Details
Published in:European Journal of Organic Chemistry 2011, Vol.2011 (7), p.1367-1375
Main Authors: Frigell, Jens, Pearcey, Jean A., Lowary, Todd L., Cumpstey, Ian
Format: Review
Language:English
Subjects:
Carbocycles
Carbohydrates
Enzymes
Glycosyl transferases
Pseudodisaccharides
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Summary:A 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. Carbasugar analogues of the two disaccharide substructures of M. tuberculosisgalactan were synthesised using an extremely regioselective opening of a carbasugar 1,2‐epoxide by alcohol nucleophilesas the key step. The pseudodisaccharides were not acceptor substrates for the enzyme GlfT2, a loss in activity compared to the parent disaccharides, but one was an inhibitor of the enzyme.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201001380