SYNTHESIS OF THIODISACCHARIDE GLYCOMIMETICS CONTAINING 6-DEOXY-FURANOSYL UNITS

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

Simposio; Canadian Glycomics Simposium; 2019

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 -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.