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Mechanisms of acrylamide and acrylamide adduct formation M. Granvogl (1), P. KOEHLER (2), P. Schieberle (2). (1) Chair for Food Chemistry, Technische Universität München, Freising, Germany; (2) German Research Center for Food Chemistry, Leibniz Institute, Freising, Germany After acrylamide was found in different kinds of processed foods in 2002, a lot of efforts have been undertaken to minimize the formation of this “food-borne” toxicant by industry and academic research. Acrylamide may be formed by the <i>Strecker</i> degradation of asparagine as well as via the <i>Amadori </i>compound of asparagine and reducing sugars or other alpha-hydroxycarbonyl compounds. In both mechanisms, 3-aminopropionamide plays a key role as a transient intermediate of acrylamide formation. Further, it is well-known that acrylamide is able to react with nucleophiles, such as thiols and primary amines, consequently leading to quite stable thioether or secondary amine formation. To elucidate the reactivity of acrylamide versus such functional groups, a number of food constituents, such as free amino acids (cysteine, lysine) and peptides (glutathione) were reacted with the unsaturated amide at different times and temperatures in model systems. After confirming the structure of the expected adducts, the respective carbon-13 labeled isotopologues were synthesized as internal standards to measure the efficacy of a given compound in acrylamide binding. In addition, it was checked whether the adducts were also able to re-liberate the bound acrylamide upon heating. Application of the newly developed stable isotope dilution assays on model systems (wheat flour) as well as on several food samples proved the presence of cysteine-acrylamide adducts in different processed foods for the first time. In the model systems, a clear dependence on the temperature as well as on the heating time was found. The varying amounts found in foods were also dependent on the processing conditions as well as on the food itself. View Presentation