THE DISULFIDE BOND AS A BUILDING MOTIF IN THE CONSTRUCTION OF MULTIVALENT LIGANDS

MARÍA EMILIA CANO; EMMANUEL BRIZZIO; MIRIAM STRUMIA; MARÍA LAURA UHRIG

Rio de Janeiro

Simposio; 30th International Carbohydrate Symposium; 2022

International Carbohydrate Organization

The development of scaffolds suitable for the multivalent presentation of sugar ligands for lectins is still an attractive synthetic challenge for carbohydrate chemists. In this work, we describe the design and synthesis of two disulfide-scaffolded multivalent ligands constructed fromdendrimeric azide-containing precursors having a thioacetate group. By click reaction (CuAAC)with thiopropargyl-sugar derivatives followed by base treatment, tetravalent and hexavalentligands were respectively obtained. The incorporation of the tioacetate group showed to be a goodalternative for the formation of the disulfide bond, as the multivalency was doubled in the same step where sugar deprotection occurs. The recognition elements introduced (RE) were tiolactose and the disaccharide Galβ(1-3)-beta-S-GalNAc, a Thomsen-Friedenreich antigen analogue (T-antigen), disaccharide which has been associated to the malignancy of certain tumors.