S-Glycosides play an important role in many aspects of carbohydrate chemistry. The ability for selective activation and relative stability of thioglycosides has led to their great popularity as donors for glycosylation reactions. The structural similarity between synthetic S-glycosides and the corresponding O-glycosides, as well as their improved stability to chemical and enzymatic hydrolysis, has generated a great deal of interest in S-linked glycoconjugates as potential glycomimetics as well as important subjects for binding studies. Biological significance has also been demonstrated by recent observations that some bacteriocins exhibit S-glycosylation of specific cysteine residues.
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Chapter 2: Monomethoxytrityl (MMTr) as an Efficient S-Protecting Group in the Manipulation of Glycosyl Thiols by Raymond Smith, Xiangming Zhu, and Elena Calatrava-Pérez
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