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Acrylamide and pyrazine formation in model systems containing asparagine.
J Agric Food Chem. 2008 Aug 13; 56(15):6105-12.JA

Abstract

The effect of different sugars and glyoxal on the formation of acrylamide in low-moisture starch-based model systems was studied, and kinetic data were obtained. Glucose was more effective than fructose, tagatose, or maltose in acrylamide formation, whereas the importance of glyoxal as a key sugar fragmentation intermediate was confirmed. Glyoxal formation was greater in model systems containing asparagine and glucose rather than fructose. A solid phase microextraction GC-MS method was employed to determine quantitatively the formation of pyrazines in model reaction systems. Substituted pyrazine formation was more evident in model systems containing fructose; however, the unsubstituted homologue, which was the only pyrazine identified in the headspace of glyoxal-asparagine systems, was formed at higher yields when aldoses were used as the reducing sugar. Highly significant correlations were obtained for the relationship between pyrazine and acrylamide formation. The importance of the tautomerization of the asparagine-carbonyl decarboxylated Schiff base in the relative yields of pyrazines and acrylamide is discussed.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Koutsidis G
Procter Department of Food Science, University of Leeds, Leeds LS2 9JT, United Kingdom. g.koutsidis@leeds.ac.uk
De la Fuente A
No affiliation info available
Dimitriou C
No affiliation info available
Kakoulli A
No affiliation info available
Wedzicha BL
No affiliation info available
Mottram DS
No affiliation info available

MeSH

AcrylamideAsparagineFructoseGas Chromatography-Mass SpectrometryGlyoxalHot TemperatureMaillard ReactionModels, ChemicalPyrazinesSchiff Bases

Pub Type(s)

Journal Article

Language

eng

PubMed ID

18624441

Citation

Koutsidis, Georgios, et al. "Acrylamide and Pyrazine Formation in Model Systems Containing Asparagine." Journal of Agricultural and Food Chemistry, vol. 56, no. 15, 2008, pp. 6105-12.
Koutsidis G, De la Fuente A, Dimitriou C, et al. Acrylamide and pyrazine formation in model systems containing asparagine. J Agric Food Chem. 2008;56(15):6105-12.
Koutsidis, G., De la Fuente, A., Dimitriou, C., Kakoulli, A., Wedzicha, B. L., & Mottram, D. S. (2008). Acrylamide and pyrazine formation in model systems containing asparagine. Journal of Agricultural and Food Chemistry, 56(15), 6105-12. https://doi.org/10.1021/jf703744k
Koutsidis G, et al. Acrylamide and Pyrazine Formation in Model Systems Containing Asparagine. J Agric Food Chem. 2008 Aug 13;56(15):6105-12. PubMed PMID: 18624441.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Acrylamide and pyrazine formation in model systems containing asparagine. AU - Koutsidis,Georgios, AU - De la Fuente,Ana, AU - Dimitriou,Chrisa, AU - Kakoulli,Antonia, AU - Wedzicha,Bronislaw L, AU - Mottram,Donald S, Y1 - 2008/07/15/ PY - 2008/7/16/pubmed PY - 2008/9/30/medline PY - 2008/7/16/entrez SP - 6105 EP - 12 JF - Journal of agricultural and food chemistry JO - J Agric Food Chem VL - 56 IS - 15 N2 - The effect of different sugars and glyoxal on the formation of acrylamide in low-moisture starch-based model systems was studied, and kinetic data were obtained. Glucose was more effective than fructose, tagatose, or maltose in acrylamide formation, whereas the importance of glyoxal as a key sugar fragmentation intermediate was confirmed. Glyoxal formation was greater in model systems containing asparagine and glucose rather than fructose. A solid phase microextraction GC-MS method was employed to determine quantitatively the formation of pyrazines in model reaction systems. Substituted pyrazine formation was more evident in model systems containing fructose; however, the unsubstituted homologue, which was the only pyrazine identified in the headspace of glyoxal-asparagine systems, was formed at higher yields when aldoses were used as the reducing sugar. Highly significant correlations were obtained for the relationship between pyrazine and acrylamide formation. The importance of the tautomerization of the asparagine-carbonyl decarboxylated Schiff base in the relative yields of pyrazines and acrylamide is discussed. SN - 1520-5118 UR - https://www.unboundmedicine.com/medline/citation/18624441/Acrylamide_and_pyrazine_formation_in_model_systems_containing_asparagine_ L2 - https://doi.org/10.1021/jf703744k DB - PRIME DP - Unbound Medicine ER -