Pyrolysis GC/MS analysis of N-(1-deoxy-D-fructos-1-yl)-L-phenylalanine: Identification of novel pyridine and naphthalene derivatives

Pyrolysis/GC/MS has been employed to analyze phenylalanine specific products formed during Maillard reaction. Phenylalanine Amadori product and different model systems containing phenylalanine and glucose, ribose, or glycerladehyde were studied. Ribbon pyrolysis was used to study the effect of temperature (150, 200, 250 degrees C) on the efficiency of formation of initial pyrolysis products from phenylalanine and Amadori phenylalanine. Quartz tube pyrolysis was used at 250 degrees C to enhance the secondary reactions. To address specific mechanistic questions, [1-C-13]glucose was used. These studies revealed the formation of pyridine and naphthalene derivatives such as 3,5-diphenylpyridine, 1(2)-naphthaleneamine, N-methyl-1(2)-aminonaphthalene, 1-aminoanthracene, 2'-phenylpyrrolo [4,5-a] dihydronaphthalene, 1(2)-(N-phenethyl)naphthaleneamine, and 1(2)-(N-phenethyl-N-methyl)naphthaleneamine. The precursors for pyridine and naphthalene derivatives were verified by GC/MS identification of the target compounds in the reaction mixtures of the postulated precursors.