Dependence and Conversion Mechanism for Selective Preparation of a Xylose-Diglycine Amadori Compound and a Cross-linking Product in an Aqueous Maillard Reaction.

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.