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Insights into the Chemistry of Non-Enzymatic Browning Reactions in Different Ribose-Amino Acid Model Systems

机译:对不同核糖氨基酸模型系统中非酶褐变反应化学的认识

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摘要

Reactions between sugars and amino acids in the Maillard reaction produce a multitude of compounds through interconnected chemical pathways. The course of the pathways changes depending on the nature of the amino acids and sugars as well as the processing conditions (e.g. temperature, water activity). Some partial pathways have been elucidated using labelled precursors but the process is very time intensive. Here, we use rapid, non-targeted analysis with Fourier transform ion cyclotron resonance mass spectrometry (FT-ICR-MS) to deliver the molecular formulae and ion intensities of the compounds generated from reaction of four amino acids with ribose (10 h at 100 °C) to study the effect of amino acid side chains on the reaction pathways. Using van Krevelen diagrams, known chemical changes during the reaction (e.g. dehydration or decarboxylation) can be studied. Comparison of the data from the four amino acids studied, showed a common pathway, which involved 73 Maillard reaction products (MRPs) where the differences were due only to the nature of the amino acid side chain. From the more than 1400 different molecular formulae found, pathways unique to the amino acids were also identified and the order of reactivity was lysine >cysteine >isoleucine ≈ glycine. While unequivocal identification of the compounds cannot be achieved with FT-ICR-MS, applying known chemical transformations found in the Maillard reaction, not only identifies new and known pathways, but also integrates the MRPs into a general Maillard reaction scheme that better represents the totality of the Maillard reaction.
机译:美拉德反应中糖和氨基酸之间的反应通过相互联系的化学途径产生了许多化合物。途径的过程取决于氨基酸和糖的性质以及加工条件(例如温度,水活度)而变化。已经使用标记的前体阐明了一些部分途径,但是该过程非常耗时。在这里,我们使用傅立叶变换离子回旋共振质谱(FT-ICR-MS)进行快速,非目标分析,以提供由四种氨基酸与核糖(10?h,在100 h下反应)生成的化合物的分子式和离子强度。 °C)以研究氨基酸侧链对反应途径的影响。使用van Krevelen图,可以研究反​​应期间已知的化学变化(例如脱水或脱羧)。比较来自所研究的四种氨基酸的数据,发现了一条共同的途径,涉及73种美拉德反应产物(MRP),其中差异仅是由于氨基酸侧链的性质所致。从发现的1400多种不同分子式中,还鉴定出了氨基酸特有的途径,反应顺序为赖氨酸>半胱氨酸>异亮氨酸≈甘氨酸。尽管用FT-ICR-MS不能明确鉴定化合物,但应用美拉德反应中发现的已知化学转化,不仅可以识别新的和已知的途径,而且还可以将MRP整合到更好地代表整体的通用美拉德反应方案中美拉德反应。

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