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Carbasugar Analogues of Galactofuranosides: Pseudodisaccharide Mimics of Fragments of Mycobacterial Arabinogalactan
Author(s) -
Frigell Jens,
Pearcey Jean A.,
Lowary Todd L.,
Cumpstey Ian
Publication year - 2011
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201001380
Subject(s) - chemistry , stereochemistry , galactan , disaccharide , regioselectivity , nucleophile , epoxide , lewis acids and bases , glycosylation , catalysis , organic chemistry , enzyme , biochemistry
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 Gal f (β1→5)Gal f was found to moderately inhibit the action of GlfT2 galactofuranosyl transferase from M. tuberculosis .