Reactivity comparison of Amadori rearrangement product formation of glycine, diglycine, and triglycine in a competing Maillard system
), Chi-Tang Hoa()Abstract
Although a certain number of amino acid-Amadori rearrangement products (ARPs) have been studied, there is still a lack of knowledge of small peptide-ARPs. Filling the gap should be a great step in the potential usage of ARP as future flavor additives. This study illustrated that small peptides (diglycine and triglycine) exhibited better relative reactivity of ARP formation than an amino acid (glycine) at relatively low temperature such as 80 and 100 ℃ and in a wide range of pH from acidic to neutral conditions, but the result reversed at high temperatures for severer instability of small peptide-ARPs. The relative reactivity of ARP formation of amino compounds in a competing Maillard systems results from dynamic systems with various factors including the chemical characterization and composition of intrinsic reactants, and parameters of matrix conditions like pH, temperature and thermal treatment time among others. Further research should be conducted to investigate peptide-ARPs, for which are ubiquitous in real food systems and worth to pay more attention.
References
Ajandouz, E.H., Tchiakpe, L.S., Dalle Ore, F., Benajiba, A., and Puigserver, A. (2001). Effects of pH on caramelization and Maillard reaction kinetics in fructose-lysine model systems. J. Food Sci. 66: 926–931.
Andrewes, P. (2012). Changes in Maillard reaction products in ghee during storage. Food Chem. 135: 921–928.
Cui, H.P., Yu, J.H., Zhai, Y., Feng, L.H., Chen, P.S., Hayat, K., Xu, Y., Zhang, X.M., and Ho, C.T. (2021). Formation and fate of Amadori rearrangement products in Maillard reaction. Trends Food Sci. Technol. 115: 391–408.
Davidek, T., Clety, N., Aubin, S., and Blank, I. (2002). Degradation of the Amadori compound N-(1-deoxy-D-fructos-1-yl)glycine in aqueous model systems. J. Agric. Food Chem. 50: 5472–5479.
Davidek, T., Marabi, A., Mauroux, O., Bauwens, I., and Kraehenbuehl, K. (2018). Preparation of activated flavor precursor DFG, N-(1-deoxy-1-fructosylglycine) by combination of vacuum evaporation and closed system heating steps. Food Chem. 244: 177–183.
Deblander, J., Van Aeken, S., Adams, A., De Kimpe, N., and Abbaspour Tehrani, K. (2015). New short and general synthesis of three key Maillard flavour compounds: 2-Acetyl-1-pyrroline, 6-acetyl-1,2,3,4-tetrahydropyridine and 5-acetyl-2,3-dihydro-4H-1,4-thiazine. Food Chem. 168: 327–331.
Ge, S.J., and Lee, T.C. (1997). Kinetic significance of the Schiff base reversion in the early-stage Maillard reaction of a phenylalanine-glucose aqueous model system. J. Agric. Food Chem. 45: 1619–1623.
Hong, P.K., and Betti, M. (2016). Non-enzymatic browning reaction of glucosamine at mild conditions: Relationship between colour formation, radical scavenging activity and alpha-dicarbonyl compounds production. Food Chem. 212: 234–243.
Luo, Y., Li, S., and Ho, C.T. (2021). Key aspects of Amadori rearrangement products as future food additives. Molecules 26: 4314–4329.
Maillard, L.C. (1912). Action of amino acids on sugars. Formation of melanoidins in a methodical way. Compt. Rend. 154: 66–68.
Martins, S.I., and Van Boekel, M.A. (2003). Kinetic modelling of Amadori N-(1-deoxy-D-fructos-1-yl)-glycine degradation pathways. Part Ⅱ-kinetic analysis.. Carbohydr Res 338: 1665–1678.
Martins, S.I.F.S., Jongen, W.M.F., and van Boekel, M.A.J.S. (2000). A review of Maillard reaction in food and implications to kinetic modelling. Trends Food Sci. Technol. 11: 364–373.
Shu, C.K., Mookherjee, B.D., and Ho, C.T. (1985). Volatile components of the thermal degradation of 2,5-dimethyl-4-hydroxy-3(2H)-furanone. J. Agric. Food Chem. 33: 446–448.
Tang, W., Cui, H., Sun, F., Yu, X., Hayat, K., Hussain, S., Tahir, M.U., Zhang, X., and Ho, C.T. (2019). N-(1-Deoxy-d-xylulos-1-yl)-glutathione: A Maillard reaction intermediate predominating in aqueous glutathione-xylose systems by simultaneous dehydration-reaction. J. Agric. Food Chem. 67: 8994–9001.
Xia, X., Zhai, Y., Cui, H., Zhang, H., Hayat, K., Zhang, X., and Ho, C.T. (2022). Glycine, diglycine, and triglycine exhibit different reactivities in the formation and degradation of Amadori compounds. J. Agric. Food Chem. 70: 14907–14918.
Yu, H., Seow, Y.X., Ong, P.K.C., and Zhou, W. (2018). Kinetic study of high-intensity ultrasound-assisted Maillard reaction in a model system of D-glucose and glycine. Food Chem. 269: 628–637.
Zhan, H., Tang, W., Cui, H., Hayat, K., Hussain, S., Tahir, M.U., Zhang, S., Zhang, X., and Ho, C.T. (2020). Formation kinetics of Maillard reaction intermediates from glycine-ribose system and improving Amadori rearrangement product through controlled thermal reaction and vacuum dehydration. Food Chem. 311: 125877.
京公网安备11010802044758号