Ammonia glycosylamine formation

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. 

Some developing solvents used in paper chromatography of sugars contain ammonia. With such solvents the formation of glycosylamines may occur. Such products may be identified by their reactions with ninhydrin 63). 

Some solvents are not stable in composition due to chemical interaction of the components, for example, n-butanol/acetic acid/water and ethyl ace-tate/pyridine/water. For reproducible results, these solvents should be freshly prepared for each separation. Tertiary alcohols are recommended for use with organic acids. The use of ammonia in solvents should be avoided since it sometimes gives rise to anomalous spots on the paper chromatogram due to formation of glycosylamines (26,216). 

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