Systematic investigation of Amadori rearrangement products for umami enhancement: synergistic binary combinations and molecular interaction mechanisms with T1R3.

BACKGROUND: Amadori rearrangement products (ARPs) are important Maillard reaction intermediates with potential taste-modulating properties, yet their binary interaction patterns and temporal sensory characteristics remain insufficiently understood. This study systematically investigated the umami-modulating properties and possible molecular basis of ARPs derived from xylose and 18 amino acids. RESULTS: Through ultra-performance liquid chromatography coupled with tandem mass spectrometry characterization and sensory evaluation, 17 ARPs showed significant umami-enhancing effects under specific conditions, with Asp-Xyl, Ile-Xyl, and Glu-Xyl exhibiting the highest maximum umami intensities. Analysis of 171 binary combinations further indicated that heterogeneous pairing (hydrophilic-hydrophobic crossover) offers a statistically superior strategy for achieving synergistic enhancement compared to homogeneous pairing. Notable synergistic effects were observed for specific combinations, including Val-Xyl/Gly-Xyl (r = 0.84) and Glu-Xyl/Leu-Xyl (r = 0.73), whereas antagonistic effects were detected in combinations such as Tyr-Xyl/Phe-Xyl. Time-intensity analysis showed that Phe-Xyl delayed the onset of umami perception and prolonged umami persistence despite its moderate maximum intensity. Molecular docking suggested possible interactions of selected ARPs with the T1R3-MSG complex, involving anchoring residues such as His23 and Arg39; however, discrepancies between docking scores and sensory enhancement indicated that binding affinity alone cannot explain umami-modulating efficacy. CONCLUSION: These findings provide a basis for developing ARP-based umami-enhancing formulations by integrating binary-combination strategies with temporal sensory profiling. © 2026 Society of Chemical Industry.