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 pr oducts formed during Maillard reaction. Phenylalanine Amadori product and different model systems containing phenylalanine and glucose, ribo se, 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 Ama dori phenylalanine. Quartz tube pyrolysis was used at 250 degrees C to enhance the secondary reactions. To address specific mechanistic ques tions, [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-aminoanthrace ne, 2'-phenylpyrrolo [4,5-a] dihydronaphthalene, 1(2)-(N-phenethyl)nap hthaleneamine, and 1(2)-(N-phenethyl-N-methyl)naphthaleneamine. The pr ecursors for pyridine and naphthalene derivatives were verified by GC/ MS identification of the target compounds in the reaction mixtures of the postulated precursors.