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

Koutsidis, Georgios, Simons, Sandra, Thong, Yeong, Haldoupis, Yannis, Mojica-Lazaro, Jonas, Wedzicha, Bronislaw and Mottram, Donald (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

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Official URL: http://dx.doi.org/10.1021/jf9014763

Abstract

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 leucine, while a significant mitigating effect, as evident from the acrylamide yields after 60 min of heating at 160 °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 α-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
Uncontrolled Keywords: acrylamide, asparagine, Maillard reaction, amino acids, proline
Subjects: F100 Chemistry
Department: Faculties > Health and Life Sciences > School of Life Sciences > Applied Sciences
Depositing User: EPrints Services
Date Deposited: 26 Feb 2010 15:38
Last Modified: 10 Aug 2015 11:43
URI: http://nrl.northumbria.ac.uk/id/eprint/1423

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