Planta Med 2008; 74 - PG1
DOI: 10.1055/s-0028-1084754

Peptides – A source of acrylamide?

J Buhlert 1, R Carle 2, Z Majer 3, D Spitzner 4
  • 1HPLC/LC-MS, Chemisches und Veterinäruntersuchungsamt Sigmaringen, Hedingerstr. 2/1, D-72488 Sigmaringen, Germany
  • 2Institute of Food Technology, Section Plant Foodstuff Technology, Universität Hohenheim, D-70593 Stuttgart, Germany
  • 3Institute of Chemistry, Dept. of Organic Chemistry, Eötvös Loránd University, H-1518 Budapest 112, Hungary
  • 4Institut für Organische Chemie, Universität Stuttgart, D-70569 Stuttgart, Germany

It is commonly accepted that the neurotoxic acrylamide 2 is mainly formed from asparagine (Asn) and a carbonyl compound, e.g. glucose, by a multi-step process (Maillard reaction) during the preparation of food at temperatures exceeding 120°C [1]. Besides this, an alternative route of formation in model studies was found which may contribute to the formation of 2 during baking [2, 3]. We found that thermal degradation of alanine and phenylalanine containing peptides e.g. 1 yielded both 2 and cinnamic amide (3) by a sequence of electrocyclic processes (domino reaction [4]) without the further involvement of a reducing sugar.

We anticipate that the thermal degradation of aspartic acid (Asp) or β-alanine (β-Ala) containing peptides may also lead to the formation of 2.

References: 1. Stadler, R. H. et al. (2002) Nature 419: 449.

2. Buhlert, J et al. (2006) Letters in Organic Chemistry 3: 356.

3. Claus, A. et al. (2006) Molecular Nutrition & Food Research 50: 87.

4. Tietze, L. F. (1996) Chem. Rev. 96: 115.