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Investigations on the effect of amino acids on acrylamide, pyrazines, and Michael addition products in model systems.
J Agric Food Chem. 2009 Oct 14; 57(19):9011-5.JA

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 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.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Koutsidis G
Procter Department of Food Science, University of Leeds, Leeds, United Kingdom. georgios.koutsidis@northumbria.ac.uk
Simons SP
No affiliation info available
Thong YH
No affiliation info available
Haldoupis Y
No affiliation info available
Mojica-Lazaro J
No affiliation info available
Wedzicha BL
No affiliation info available
Mottram DS
No affiliation info available

MeSH

AcrylamideAmino AcidsAsparagineGlucoseGlycineHot TemperatureMaillard ReactionModels, ChemicalPyrazines

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

19739658

Citation

Koutsidis, Georgios, et al. "Investigations On the Effect of Amino Acids On Acrylamide, Pyrazines, and Michael Addition Products in Model Systems." Journal of Agricultural and Food Chemistry, vol. 57, no. 19, 2009, pp. 9011-5.
Koutsidis G, Simons SP, Thong YH, et al. Investigations on the effect of amino acids on acrylamide, pyrazines, and Michael addition products in model systems. J Agric Food Chem. 2009;57(19):9011-5.
Koutsidis, G., Simons, S. P., Thong, Y. H., Haldoupis, Y., Mojica-Lazaro, J., Wedzicha, B. L., & 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), 9011-5. https://doi.org/10.1021/jf9014763
Koutsidis G, et al. Investigations On the Effect of Amino Acids On Acrylamide, Pyrazines, and Michael Addition Products in Model Systems. J Agric Food Chem. 2009 Oct 14;57(19):9011-5. PubMed PMID: 19739658.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Investigations on the effect of amino acids on acrylamide, pyrazines, and Michael addition products in model systems. AU - Koutsidis,Georgios, AU - Simons,Sandra P J, AU - Thong,Yeong H, AU - Haldoupis,Yannis, AU - Mojica-Lazaro,Jonas, AU - Wedzicha,Bronislaw L, AU - Mottram,Donald S, PY - 2009/9/11/entrez PY - 2009/9/11/pubmed PY - 2010/1/29/medline SP - 9011 EP - 5 JF - Journal of agricultural and food chemistry JO - J Agric Food Chem VL - 57 IS - 19 N2 - 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 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. SN - 1520-5118 UR - https://www.unboundmedicine.com/medline/citation/19739658/Investigations_on_the_effect_of_amino_acids_on_acrylamide_pyrazines_and_Michael_addition_products_in_model_systems_ L2 - https://doi.org/10.1021/jf9014763 DB - PRIME DP - Unbound Medicine ER -