Dependence and Conversion Mechanism for Selective Preparation of a Xylose–Diglycine Amadori Compound and a Cross-linking Product in an Aqueous Maillard Reaction
Mengyu Ma, Heping Cui, Ziyan Wang, Khizar Hayat, Chengsheng Jia, Yan Xu, Xiaoming Zhang, Chi‐Tang Ho
Abstract
The structure of the prepared Amadori rearrangement product of xylose-glycylglycine (XGG-ARP) and a cross-linking product (XGG-CP) was first characterized by liquid chromatography-mass spectrometry (LC-MS)/MS and NMR analysis, respectively. The dependences were then studied for the formation of XGG-ARP and XGG-CP in an aqueous Maillard reaction of a xylose-glycylglycine model system. The influence factors were the reaction temperature, pH, molar ratio of reactants, and the reaction time. It was found that XGG-ARP would acquire the highest yield of 73.8% when the thermal reaction was carried out at 70 °C and pH 8.0 for 10 min. A higher temperature and a lower pH might enhance the yield of the formation of XGG-CP. Combining the low-temperature dehydration reaction with the high-temperature aqueous-phase Maillard reaction increased the XGG-CP yield to 43.54%. The efficient and selective preparation of XGG-ARP and XGG-CP was controllable through the adjustment of reaction conditions. Moreover, the pathway of XGG-CP formation from XGG-ARP and Gly-Gly by the aldimine condensation reaction was also proposed. The high stability of an XGG-CP molecule enhanced by its p-π-p conjugated structure inhibited the occurrence of the Amadori rearrangement and led to a non-keto structure, blocking the further Maillard reaction of XGG-CP.