Investigations on the effect of amino acids on acrylamide, pyrazines, and Michael addition products in model systems

Koutsidis, G., Simons, S.P.J., Thong, Y.H., Haldoupis, Y., Mojica-Lazaro, J., Wedzicha, B.L. and Mottram, D.S. (2009) Investigations on the effect of amino acids on acrylamide, pyrazines, and Michael addition products in model systems. Journal of Agricultural and Food Chemistry, 57 (19). pp. 9011-9015. ISSN 0021-8561 doi: 10.1021/jf9014763

Abstract/Summary

Acrylamide and pyrazine formation, as influenced by the incorporation of different amino acids, was investigated in sealed low-moisture asparagine-glucose model systems. Added amino acids, with the exception of glycine and cysteine and at an equimolar concentration to asparagine, increased the rate of acrylamide formation. The strong correlation between the unsubstituted pyrazine and acrylamide suggests the promotion of the formation of Maillard reaction intermediates, and in particular glyoxal, as the determining mode of-action. At increased amino acid concentrations, diverse effects were observed. The initial rates of acrylamide formation remained high for valine, alanine, phenylalanine, tryptophan, glutamine, and Ieucine, while a significant mitigating effect, as evident from the acrylamide yields after 60 min of heating at 160 degrees C, was observed for proline, tryptophan, glycine, and cysteine. The secondary amine containing amino acids, proline and tryptophan, had the most profound mitigating effect on acrylamide after 60 min of heating. The relative importance of the competing effect of added amino acids for alpha-dicarbonyls and acrylamide-amino, acid alkylation reactions is discussed and accompanied by data on the relative formation rates of selected amino acid-AA adducts.

Item Type	Article
URI	https://reading-clone.eprints-hosting.org/id/eprint/13236
Item Type	Article
Refereed	Yes
Divisions	Life Sciences > School of Chemistry, Food and Pharmacy > Department of Food and Nutritional Sciences
Uncontrolled Keywords	Acrylamide, asparagine, Maillard reaction, amino acids, proline , MAILLARD REACTION, POTATO, GLYCINE, ELIMINATION, ASPARAGINE, PRECURSORS, REDUCTION, KINETICS, BREAD, YEAST
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