title: Synthesis of the (1→6)-linked thiodisaccharide of galactofuranose: inhibitory activity against a β-galactofuranosidase.
abstract: A new (1→6)-linked thiodisaccharide formed by two galactofuranosyl units has been synthesized. Methyl (methyl α,β-D-galactofuranosid)uronate was employed as the starting compound, which was per-O-silylated with TBSCl and reduced with LiAlH4 to afford methyl 2,3,5-tri-O-tert-butyldimethylsilyl-β-D-galactofuranoside (2β) as a key precursor for the preparation of methyl per-O-tert-butyldimethylsilyl-6-thio-β-D-galactofuranoside (12). The free thiol group of 12 was glycosylated and the product O-deprotected to afford the target β-D-Galf-S-(1→6)-β-d-Galf-OMe (14). The conformations of this thiodisaccharide were preliminarily studied using combined theoretical calculations and NMR data. Furthermore, the glycomimetic 14 showed to be a competitive inhibitor of the β-galactofuranosidase from Penicillum fellutanum (K(i)=3.62 mM).
authors.affiliation: CIHIDECAR-CONICET-UBA, Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Buenos Aires 1428, Argentina.
authors.forename: Evangelina
authors.initials: E
authors.lastname: Repetto
authors.forename: Carla
authors.initials: C
authors.lastname: Marino
authors.forename: Oscar
authors.initials: O
authors.lastname: Varela
mesh_terms: D000935:Antifungal Agents / Q000138:chemical synthesis* / Q000737:chemistry; D002236:Carbohydrate Conformation; D004187:Disaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D005656:Fungal Proteins / Q000037:antagonists & inhibitors* / Q000737:chemistry; D005690:Galactose / Q000737:chemistry*; D006026:Glycoside Hydrolases / Q000037:antagonists & inhibitors* / Q000737:chemistry; D006031:Glycosylation; D007700:Kinetics; D009682:Magnetic Resonance Spectroscopy; D010407:Penicillium / Q000737:chemistry* / Q000201:enzymology; D013862:Thiogalactosides / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000935:Antifungal Agents; D004187:Disaccharides; D005656:Fungal Proteins; D013862:Thiogalactosides; C584671:methyl 6-S-(galactofuranosyl)-6-thiogalactofuranoside; D006026:Glycoside Hydrolases; C023112:exo-beta-D-galactofuranosidase; D005690:Galactose