Synthesis of thiodisaccharides glycommimetics containing 6-deoxy-furanosyl units

LO FIEGO, MARCOS J.; HOBSTETER, ARIANA; HOLST, VIRGINIA; SILBESTRI, GUSTAVO F.; MARINO, CARLA; VARELA, OSCAR

Banff, Alberta

Simposio; 4th Canadian Glycomics Symposium; 2019

Canadian Glycomics Networks (GLYCONET)

The interest in galactofuranose-containing molecules arises from the fact that Galf is present in glycoconjugates that are considered to be essential for the survival or virulence of pathogenic microorganisms, but is absent in higher eukaryotes. We have synthesized two thioglycomimetics of β-D-Galf-(1→5)-D-Galf, a motif present in glycoconjugates of many pathogenic microorganisms. These β-D-thiodisaccharides contain 1-thio-D-galactofuranose as non reducing unit and alternatively 6-deoxy-5-thio derivatives of L-Altf or D-Galf the reducing end. Both thiodisaccharides showed to be competitive inhibitors of the β-D-galactofuranosidase from Penicillium fellutanum. In this communication is presented the progress towards the synthesis of new thioglycomimetics containing 6-deoxy-furanosyl units.