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含天冬酰胺的模型体系中丙烯酰胺和吡嗪的形成

Acrylamide and pyrazine formation in model systems containing asparagine.

作者信息

Koutsidis Georgios, De la Fuente Ana, Dimitriou Chrisa, Kakoulli Antonia, Wedzicha Bronislaw L, Mottram Donald S

机构信息

Procter Department of Food Science, University of Leeds, Leeds LS2 9JT, United Kingdom.

出版信息

J Agric Food Chem. 2008 Aug 13;56(15):6105-12. doi: 10.1021/jf703744k. Epub 2008 Jul 15.

DOI:10.1021/jf703744k
PMID:18624441
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.

摘要

研究了不同糖类和乙二醛对低水分淀粉基模型体系中丙烯酰胺形成的影响,并获得了动力学数据。在丙烯酰胺形成方面,葡萄糖比果糖、塔格糖或麦芽糖更有效,同时证实了乙二醛作为关键糖裂解中间体的重要性。在含有天冬酰胺和葡萄糖而非果糖的模型体系中,乙二醛的形成更多。采用固相微萃取气相色谱 - 质谱法对模型反应体系中吡嗪的形成进行定量测定。在含有果糖的模型体系中,取代吡嗪的形成更为明显;然而,当使用醛糖作为还原糖时,未取代的同系物(这是在乙二醛 - 天冬酰胺体系顶空中唯一鉴定出的吡嗪)以更高的产率形成。吡嗪与丙烯酰胺形成之间的关系获得了高度显著的相关性。讨论了天冬酰胺 - 羰基脱羧席夫碱的互变异构在吡嗪和丙烯酰胺相对产率中的重要性。

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