From thiosugars and thiodisaccharides to supramolecular multivalent ligands

MARÍA LAURA UHRIG

Tiradentes

Congreso; 18th BRAZILIAN MEETING ON ORGANIC SYNTHESIS; 2022

Thioglycosides and thiodisaccharides represent a synthetic challenge for carbohydrate chemists due to their increasing importance in the Glycobiology field. In these compounds, the anomeric oxygen has been replaced by a sulfur atom, and so, they are considered carbohydrate mimetics with great potential as enzyme inhibitors or new ligands for lectins, given that this replacement does not interfere with recognition events. Moreover, this structural feature makes them more resistant towards enzymatic and acidic hydrolysis. Therefore, the development of new synthetic methods to obtain thiosugars and their use as building blocks for the synthesis of new carbohydrate-derived compounds have been an active research field over the years. In our laboratory, we are interested in developing multivalent systems with high affinity for lectins, constructed from glycomimetics such as thiosugars and thiodisaccharides. Thus, after exploring a range of covalently-constructed multivalent structures, we undertook the study of self-assembled multivalent systems produced from amphiphilic compounds. In all cases, we have incorporated thiosugars such as 1-thiolactose, β-S-N-acetylglucosamine and even thiodisaccharides as recognition elements, which were, at the same time, the polar moiety of the amphihile. Pyrene and resorcinarene systems, as well as long chain diacyl-derived tartaric residues, have been used as hydrophobic residues. Thus, in this presentation I will refer to our latest results on the synthesis and characterization of supramolecular multivalent ligands for lectins. It will include the synthetic results regarding the construction of GlcNAc-thiodisaccharides, and also our experience on a variety of self-assembled and micellar systems, including gels, which have shown high affinity for model lectins.