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Amadori rearrangement products (ARPs), as intermediates of the Maillard reaction (MR), are potential natural flavor additives but there is a lack of investigation especially in oligopeptide-ARPs. This study for the first time conducted a systematic analysis in comparing ARPs of glycine, diglycine, triglycine, and glucose to corresponding classic MR systems, including production, stability, and flavor analysis. The ARPs were effectively produced by prelyophilization with heating at 70 °C for 60 min and purified to 96% by a two-step purification method. Correlated with the stability order of amino compounds (glycine > diglycine > triglycine), the stability order of ARPs was Gly-ARP > Digly-ARP ≈ Trigly-ARP. In a negative correlation with heating temperature and time, ARPs were less stable than original amino compounds at high temperatures (100, 130, and 160 °C). ARPs exhibited better flavor formation ability in pyrazines and furans than MR systems, with similar flavor compositions but different preferences. Diglycine- and triglycine-ARPs exhibited better flavor formation efficiency than glycine-ARP. Heating temperature and time, initial pH, and carbon chain length were found to be the parameters that affect the stability and flavor formation of ARPs. This study suggested that ARPs, especially peptide-ARPs, have great potential for usage as food flavor additives in the future.

A series of Amadori compounds of glucose were prepared from glycine (G-ARP), diglycine (DiG-ARP), and triglycine (TriG-ARP), and identified by UPLC-MS/MS and NMR. The formation rate of ARPs was TriG-ARP > DiG-ARP > G-ARP, and their activation energies were 63.48 kJ/mol (TriG-ARP), 72.84 kJ/mol (DiG-ARP), and 84.76 kJ/mol (G-ARP), respectively, suggesting that ARP was formed more easily from small peptides than from amino acid. Although 1-DG was formed much more difficultly than 3-DG, the same order of the formation of 1-DG, 3-DG, and browning was DiGly > TriGly > Gly. It was also confirmed that more methylglyoxal and glyoxal would be formed from small peptides than equimolar amino acids. Compared with free amino acid, ARP, deoxyglycosones, and their secondary degradation products were more easily formed from dipeptide and tripeptide, thereby stronger browning occurred and higher reactivity was exhibited in Maillard reaction of di- or tripeptide.

The role of amino acids and α-dicarbonyls in the flavor formation of Amadori rearrangement product (ARP) during thermal processing was investigated. Comparisons of the volatile compounds and their concentrations when N-(1-deoxy-α-d-ribulos-1-yl)-glycine reacted with different amino acids or glyoxal (GO) at 100 °C were executed. Additional amino acids, such as glycine (Gly), in ARP models contributed to the diversity of furanoids by the chain elongation of the derived formaldehyde. Whereas the monoanion of additional glutamic acid acted as nucleophile, favored 2-ethyl-3,5-dimethylpyrazine and 2,5-dimethylpyrazine formation; the nonionized amino group of additional lysine were involved in α-dicarbonyls formation, causing pyrazine and methylpyrazine accumulation in the ARP model. Moreover, the high dosage and pH stabilization of additional GO probably promoted the ARP degradation and deoxyosones retro-aldol cleavage, resulting in methylpyrazine rather than furanoids formation. The present work provided the guidance for the controlled flavor formation of ARP in industrial application., (Copyright © 2021 Elsevier Ltd. All rights reserved.)

The effect of ellagic acid on the formation of pyrazine, methylpyrazine, 2,3-methylpyrazine, 2,6-methylpyrazine, 2,5-methylpyrazine, and trimethylpyrazine in the xylose-glycine Maillard reaction model was researched. Ellagic acid could either inhibit or promote pyrazine formation, depending on its addition time point and the pH of the system. The addition of ellagic acid during the accumulation period of an Amadori compound inhibited pyrazine formation by capturing the Amadori compound in the xylose-glycine Maillard system and decreasing the pyrazine precursors. The inhibitory effect of ellagic acid on pyrazine formation got more obvious with an increase in the pH of the system. However, when ellagic acid was added at the beginning of the xylose and glycine Maillard system and when the oxidizing substances such as glyoxal and methylglyoxal were significantly formed in the Maillard system, its oxidation could promote the formation of pyrazines.

Amadori rearrangement product (ARP) is an ideal flavor precursor. The formation kinetics of ARP from glycine-ribose system, 3-deoxyribosone (3-DR) and 1-deoxyribosone (1-DR) were evaluated, and then controlled thermal reaction (CTR) coupled with vacuum dehydration was proposed to improve the ARP yield. As key factors controlling the formation of byproducts, CTR temperature and time were optimized as 100 °C, 60 min based on the formation kinetics of the ARP and deoxyribosones. Vacuum dehydration was further used to increase the ARP yield from 0.77% to 64.50%, which was improved by 82.8 times, while 3-DR and 1-DR yield increased only by 1.5 and 3.7 times, respectively. The formation of ARP was the dominant reaction during vacuum dehydration. Under optimal conditions, CTR coupled with vacuum dehydration was an effective method to control byproducts formation and improve the ARP yield simultaneously. This method may offer a potential application in flavor enhancement of light-color food., (Copyright © 2019 Elsevier Ltd. All rights reserved.)

Unexpected browning was observed in sorbitol and amino acid system under high-temperature process and long-term storage. The effect of glycerol on the browning reaction of sorbitol-glycine model system under different heat treatment time was explored. The results confirmed that partial sorbitol was converted to glucose and fructose, which underwent a Maillard reaction with glycine to produce the melanoidins. Glycerol concentration and the heating time were positively correlated with the course of the reaction, which reflected in the increase of browning index, the rise of uncolored intermediate products and fluorescent substance accumulation. Compared with the system without glycerol, the browning index increased by about 100 times and the accumulation of uncolored intermediate products increased by 65 times with the presence of 4 mol/L glycerol. Furthermore, the content of α-dicarbonyl compounds (glyoxal, methylglyoxal and 2, 3-butanedione) in the system was changed by glycerol, which showed a trend of first increasing and then decreasing with the accumulation of melanoidins, and reached a peak value of 190.6 mg/L after heating for 2 h. The glycerol-dependent browning was related to the water activity of the system at a high level (>0.80) and the migration rate of free water to immobilized water ranging from 0.60% to 8.59%. It indicated that glycerol could promote the reaction by influencing the substrate concentration, weakening the inhibition of product and promoting the conversion of sorbitol to reducing sugar. [Display omitted] • Glycerol promoted browning of the sorbitol-glycine system. • The system produced reducing sugar conversion and Maillard reaction by heat treatment. • The degree of Maillard reaction was positively related to the glycerol concentration. • Glycerol facilitated the reaction by influencing the state of water status. [ABSTRACT FROM AUTHOR]

[Display omitted] Browning can occur in the matrices of alditol and amino acids due to heating or long-term storage, which poses challenges in achieving the desired appearance stability. To investigate the mechanism of browning in the sorbitol-glycine system, we evaluated the evolution of typical intermediates, including glucose and α-dicarbonyl compounds (α-DCs), during heating at 100 ˚C. The browning index and intermediate products of the sorbitol-glycine system increased more rapidly compared to those of the sorbitol system. After heating for 10 h, the browning index of the sorbitol-glycine system was eight times higher than that of sorbitol alone. In the presence of glycine, sorbitol underwent continuous conversion into glucose. After 10 h of heating, the concentration of glucose in the sorbitol-glycine system reanched 726.6 mg/L, which was approximately 63 times higher than that in the sorbitol system. Mass spectrometry analysis revealed the presence of α-DCs such as 3-deoxyglucosone (3-DG), glyoxal (GO), methylglyoxal (MGO), 2,3-butanedione (2,3-BD), in the sorbitol-glycine system. These compounds were precursors of melanoidins, indicating the occurrence of the Maillard reaction and resulting in the browning of the system. Therefore, the browning process in the sorbitol-glycine system involved two stages of reactions: the conversion of sorbitol to glucose and the Maillard reaction between glucose and glycine. [ABSTRACT FROM AUTHOR]