title: Thermally generated 3-aminopropionamide as a transient intermediate in the formation of acrylamide.
abstract: On the basis of the recent findings that "biogenic amines" can also be formed during thermal food processing from their parent amino acids in a Strecker-type reaction, the formation of 3-aminopropionamide, the biogenic amine of asparagine, was investigated in model systems as well as in thermally processed Gouda cheese. The results of model studies revealed that, besides acrylamide, 3-aminopropionamide was also formed in amounts of 0.1-0.4 mol % when asparagine was reacted in the presence of either glucose or 2-oxopropionic acid. Results of a second series of model experiments in which [(13)C(4)(15)N(2)]-asparagine ([(13)C(4)(15)N(2)]-Asn) and unlabeled 3-aminopropionamide were reacted together in the presence of glucose revealed a >12-fold higher efficacy of 3-aminopropionamide in acrylamide generation as compared to asparagine. Both [(13)C(3)(15)N(2)]-3-aminopropionamide and [(13)C(3)(15)N(1)]-acrylamide were formed during [(13)C(4)(15)N(2)]-Asn degradation in a ratio of about 1:4, supporting the idea that 3-aminopropionamide is a transient intermediate in acrylamide formation. In this study, 3-aminopropionamide was identified and quantified for the first time in foods, namely, in Gouda cheese. Although the fresh cheese contained low amounts of 3-aminopropionamide, its concentrations were much increased to approximately 1300 mug/kg after thermal processing. In isotope labeling studies, performed by administering to the cheese [(13)C(4)(15)N(2)]-Asn in a ratio of 1:2 as compared to the "natural" concentrations of asparagine, similar ratios of unlabeled/labeled 3-aminopropionamide and unlabeled/labeled acrylamide were determined. Thus, 3-aminopropionamide could be verified as a transient intermediate of acrylamide formation during food processing.
authors.affiliation: Chair for Food Chemistry, Technical University of Munich, Garching, Germany.
authors.forename: Michael
authors.initials: M
authors.lastname: Granvogl
authors.forename: Peter
authors.initials: P
authors.lastname: Schieberle
mesh_terms: D020106:Acrylamide / Q000737:chemistry*; D001216:Asparagine / Q000737:chemistry; D002611:Cheese / Q000032:analysis*; D005947:Glucose / Q000737:chemistry; D006358:Hot Temperature; D015091:beta-Alanine / Q000031:analogs & derivatives* / Q000737:chemistry
chemical_list: D015091:beta-Alanine; D020106:Acrylamide; C012731:beta-alanine amide; D001216:Asparagine; D005947:Glucose