S-, N-, C-, and O-glycosidic Bonds
Glycosidic bonds of the form discussed above known as O-glycosidic bonds, in reference to the glycosidic oxygen that links the glycoside to the aglycone or reducing end sugar. In analogy, one also considers S-glycosidic bonds (which form thioglycosides), where the oxygen of the glycosidic bond is replaced with a sulfur atom. In the same way, N-glycosidic bonds, have the glycosidic bond oxygen replaced with nitrogen. Substances containing N-glycosidic bonds are also known as glycosylamines; the term "N-glycoside" is considered a misnomer by IUPAC and is discouraged. C-glycosyl bonds have the glycosidic oxygen replaced by a carbon. All of these modified glycosidic bonds have different susceptibility to hydrolysis, and in the case of C-glycosyl structures, they are typically more resistant to hydrolysis.
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