2-Deoxy sugars are present in many bioactive natural products and clinical agents and significantly influence their biological activity as well as stability and solubility. Despite their critical role, the glycosidic linkage of 2-deoxy glycosides has been found to be susceptible to hydrolysis in acid media or by glycosyl hydrolases, which has made it difficult to probe the biological role of these 2-deoxy sugars, has resulted in toxicity and reduced activity of the parent molecules, and has limited their use as clinical agents. Thioglycosides(S-linked glycosides), in which the glycosidic oxygen atom is replaced by a sulfur atom, are resistant towards enzymatic cleavage as well as chemical degradation. In addition, thioglycosides maintain the biological activity of their parent O-linked glycosides and are tolerated by most biological systems. Therefore, they can be employed as an important tool for structural biology and attractive therapeutic agents. In this presentation, I will discuss the development of new glycosylation methods for stereoselective synthesis of S-linked 2-deoxy sugars for comparisons of their physical, chemical and biological properties with natural O-linked counterparts.

Stereoselective synthesis of S-linked 2-deoxy sugars for biological studies

247th National Meeting (2014)

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