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

Abstract

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.

Dietary Advanced Glycation Endproducts and the Gastrointestinal Tract

“…To identify the products formed during the MR, Hemmler et al (2018) recently used a non-targeted analysis with Fourier transform ion cyclotron resonance mass spectrometry (FT-ICR-MS) to derive the molecular formulae of compounds formed after 10 h of heating at 100 • C for different sugar-amino acid combinations [132]. The reaction rate order that was found for amino acids was: Lysine > cysteine > isoleucine ≈ glycine.…”

Physicochemical and sensory characterization of bread produced from different dough formulations by Kluyveromyces lactis

“…One another reason may be the amino acid residues contained in whey, which is a rich source of the essential amino acids such as lysine, methionine, threonine, and histidine (Gorissen et al., 2018). In many studies investigating the nonenzymatic browning reactions in model systems, it was shown that the lysine is the most reactive amino acid (Ajandouz & Puigserver, 1999; Ashoor & Zent, 1984; Hemmler et al., 2018). Shen, Tebben, Chen, and Li (2018) studied on the effects of different amino acids on bread properties and reported that breads with darker and less yellowish crust colors were obtained with the addition of amino acids.…”

Gastrointestinal digestion of dietary advanced glycation endproducts using anin vitromodel of the gastrointestinal tract (TIM-1)

“…A second mechanism for the formation of endogenous AGEs in the GI tract could therefore be the presence of fructose in the ginger biscuit, which is highly reactive in the Maillard reaction due to its reduced stability of the ring structure compared to glucose. 32 Although conflicting evidence exists on whether there is a correlation between dAGE uptake and AGE serum and urine levels, a perspective by DeChristopher published in 2017 proposed that a source for increased serum AGE levels may be the formation of AGEs in the GI tract. 33 Fructose is actively absorbed in the human GI tract together with glucose in a 1 : 1 ratio.…”