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Reactions of Dehydroascorbic Acid with Primary Aliphatic Amines Including N α -Acetyllysine

1996; American Chemical Society; Volume: 44; Issue: 7 Linguagem: Inglês

10.1021/jf9601426

1520-5118

Bernd Larisch, Monika Pischetsrieder, Theodor Severin,

Diet, Metabolism, and Disease

The reaction of l-dehydroascorbic acid (DHA) with primary aliphatic amines including Nα-acetyllysine was examined by HPLC. A new aminoreductone, 2-deoxy-2-(propylamino)ascorbic acid (1) was isolated and the structure elucidated by spectroscopic data. Furthermore oxalic acid mono- (2) and diamides (3) were identified as important degradation products of DHA under Maillard conditions. 3-Deoxy-3-(alkylamino)ascorbic acids (4), typical condensation products of l-ascorbic acid and amines, were also detected in the reaction mixtures of DHA. All products are formed under oxidative and nonoxidative conditions from DHA. Keywords: Maillard reaction; l-dehydroascorbic acid; l-ascorbic acid; oxalic acid amides; aminoreductones; protein glycation; protein cross link