Formation of pyrroles, 2-pyrrolidones, and pyridones by heating of 4-aminobutyric acid and reducing sugars

摘要: The Maillard reaction of 4-aminobutyric acid with reducing sugar (D-arabinose, D-glucose, L-rhamnose, D-fructose, maltose) was investigated in slightly acidic aqueous media. Eight pyrroles, 14 2-pyrrolidones, and 2 4-pyridones were characterized quantified by capillary GC/MS. For structure elucidation the compounds separated preparative GC or synthesized MS, IR, 1 H NMR spectroscopy. Due to a blocked Strecker degradation, specific products are comparable those peptide-bound L-lysine. Thus, title generated D-glucose maltose/4-aminobutyric model experiments structurally related E-pyrrolonorleucine maltosine, respectively