Abstract
Drugs with a primary aromatic amino moiety such as procaine, procainamide, and p-aminobenzoic acid (PABA) are capable of reacting with various reducing sugars containing hexoaldoses and pentoaldoses. The amine-carbohydrate reaction products can be separated from the parent drugs by high performance liquid chromatography (HPLC) analysis. The formation and dissociation profiles of the products were followed by HPLC and ultraviolet spectroscopy. The reaction products formed in aqueous solution were not association complexes, but chemical reaction products, which were identified as glycosylamines or N-glycosides, by comparison with authentic samples obtained by the condensation of amines with carbohydrates in methanol. An X-ray analysis of one of the glycosylamines, 2-deoxy-N-p-carboxyphenyl-D-ribosylamine, was carried out, and the absolute conformation and configuration in the crystalline state were determined.
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