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10.5: N-glycosidic Bonds - Chemistry LibreTexts

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We have just seen that when a second alcohol attacks a hemiacetal or hemiketal, the result is an acetal or ketal, with the glycosidic bonds in carbohydrates providing a biochemical example. But if a …

We have just seen that when a second alcohol attacks a hemiacetal or hemiketal, the result is an acetal or ketal, with the glycosidic bonds in carbohydrates providing a biochemical example. But if a hemiacetal is attacked not by a second alcohol but by an amine, what results is a kind of 'mixed acetal' in which the anomeric carbon is bonded to one oxygen and one nitrogen. This arrangement is referred to by biochemists as an N-glycosidic bond. You may recognize these as the bonds in nucleosides and nucleotides that link the G, C, A, T, or U base to the sugar. The formation of \(N\)-glycosidic b

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