The effect of simultaneous dehydration-reaction (SDR) on Amadori rearrangement product (ARP) N-(1-deoxy-d-xylulos-1-yl)-glutathione and its key degradation products, 3-deoxyxylosone (3-DX) and 1-deoxyxylosone (1-DX), were investigated in an aqueous glutathione-xylose (GSH-Xyl) system. The yield of ARP was increased to 67.98% by SDR compared with 8.44% by atmospheric thermal reaction at 80 °C. Reaction kinetics was applied to analyze the mechanism and characteristics of ARP formation and degradation under SDR. ARP formation and degradation rate was highly dependent on temperature, and the latter was more sensitive to temperature. By regulating the reaction conditions of temperature and pH, the ratio of ARP formation rate constant to its degradation rate constant could be controlled to achieve an efficient preparation of ARP from GSH-Xyl Maillard reaction through SDR.

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The formation conditions of the Amadori compound (ARP) N-(1-deoxy-d-xylulos-1-yl)-alanine were determined in an aqueous Maillard reaction between l-alanine and d-xylose under a two-step temperature rising process with (−)-epigallocatechin gallate (EGCG) as an indicator followed by browning intensity detection of the final Maillard reaction products (MRPs). To clarify the mechanism of EGCG indication on the ARP formation, the change in the concentration of some key products generated during the Maillard reaction with EGCG addition was investigated. Results showed an inhibition effect of EGCG on the browning precursor formation through the generation of ARP-EGCG adducts and deoxyosone-EGCG adducts, which was proposed as an important pathway to inhibit browning during the Maillard reaction and to indicate ARP formation.