ORCID

https://orcid.org/0000-0001-5845-7407

Date of Award

2025

Document Type

Dissertation

Degree Name

Pharmaceutical Sciences (Ph.D.)

Department

Pharmaceutical Sciences

First Advisor

Carlos S Chavez

Second Advisor

Vijaya Korlipara

Third Advisor

Tanaji Talele

Abstract

This thesis dives into two relevant fields in carbohydrate science: reactivity and conformation. We centered our attention on S-glycosides, a common class of glycosyl donors and glycomimetics, to study the influence exerted by the structural architecture over the conformational properties about flexible bonds and the reactivity towards electrochemical activation. Studying the conformational properties of sugars is key to understanding the molecular recognition mechanisms underlying their biological functions. Moreover, a well understanding of how the molecular components affect free rotation about bonds can be valuable information to design improved glycomimetic drug candidates. On the other hand, electrosynthesis is a promising application in carbohydtrate chemistry, particularly as an alternative to construct glycosidic bonds. Our current knowledge on electrochemical glycosylation is limited to glycosylation reactions involving aryl S-glycosides as electroactive glycosyl donors. In this work, we explored the reactivity patterns of alkyl S-glycosides and positioned these compounds as an excellent alternative to conduct electrochemical glycosylations. Finally, we devoted our efforts to synthesize carbohydrate antigens associated with Schistosoma mansoni, the second most important tropical neglected disease, for further development of antischistosomiasis carbohydrate-based vaccine candidates. We describe a synthetic approach to the disaccharide core LacdiNAc (LDN), which is present in the major Schistosoma’s carbohydrate antigen.

Download

Included in

Chemistry Commons

Share

COinS