1. Thiodisaccharides with galactofuranose or arabinofuranose as terminal units: synthesis and inhibitory activity of an exo beta-D-galactofuranosidase
- Author
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M. Laura Uhrig, Carla Marino, Evangelina Repetto, and Oscar Varela
- Subjects
Glycoside Hydrolases ,Stereochemistry ,Clinical Biochemistry ,Disaccharide ,Pharmaceutical Science ,Sulfides ,Disaccharides ,Biochemistry ,Chemical synthesis ,Catalysis ,chemistry.chemical_compound ,Drug Discovery ,Glycosyl ,Enzyme Inhibitors ,Molecular Biology ,chemistry.chemical_classification ,biology ,Organic Chemistry ,Penicillium ,Galactose ,Tin Compounds ,Oxides ,Furanose ,Arabinose ,Enzyme ,chemistry ,Manganese Compounds ,Enzyme inhibitor ,Michael reaction ,biology.protein ,Molecular Medicine ,Chlorine Compounds ,Enone - Abstract
Thiodisaccharides having beta-D-Galf or alpha-L-Araf units as non-reducing end have been synthesized by the SnCl(4)- or MoO(2)Cl(2)-promoted thioglycosylation of per-O-benzoyl-D-galactofuranose (1), its 1-O-acetyl analogue 4, or per-O-acetyl-alpha-L-arabinofuranose (16) with 6-thioglucose or 6-thiogalactose derivatives. After convenient removal of the protecting groups, the free thiodisaccharides having the basic structure beta-D-Galf(1-->6)-6-thio-alpha-D-Glcp-OMe (5) or beta-D-Galf(1-->6)-6-thio-alpha-D-Galp-OMe (15) were obtained. The respective alpha-L-Araf analogues 18 and 20 were prepared similarly from 16. Alternatively, beta-D-Galf(1-->4)-4-thio-3-deoxy-alpha-L-Xylp-OiPr was synthesized by Michael addition to a sugar enone of 1-thio-beta-d-Galf derivative, generated in situ from the glycosyl isothiourea derivative of 1. The free S-linked disaccharides were evaluated as inhibitors of the beta-galactofuranosidase from Penicillium fellutanum, being 15 and 20 the more active inhibitors against this enzyme.
- Published
- 2008