Formation, Anomerisation, and Hydrolysis of Glycosylamines

The pH (or Ho - see Chapter 3, footnote xi) dependences of the rates of hydrolysis of glycosylamines are bell-shaped, with the maximimum at a pH 

Glycosylamines from simple secondary amines, such as N-glycosyl piperidine, appear to behave like glycosylamines derived from primary amines and ammonia. Where, however, formation of a cationic Schiif base would involve disruption of an aromatic sextet (as with glycosyl imidazoles, pyrazoles and purines) the glycosylamines are configurationally stable. 

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