Recent research indicates that N-lactoyl amino acid derivatives have the potential as kokumi substances, with their kokumi profile closely linked to that of amino acids. This study aimed to explore the unexplored effects resulting from the introduction of lactate groups into l-Methional (l-Met), a prevalent flavor compound found in foods, such as tomatoes, known for its ability to activate the monosodium glutamate response. N-l-Lac-l-Met was enzymatically synthesized using food grade, and its taste profile and underlying mechanisms were investigated. The structure of N-l-Lac-l-Met was determined by high-performance liquid chromatography (HPLC)-mass spectrometry (MS)/MS. Sensory evaluation revealed the presence of astringency, kokumi, and bitterness of N-l-Lac-l-Met. In a stimulated broth, N-l-Lac-l-Met exhibited enhanced umami and kokumi taste perception compared to l-Met while demonstrating good stability within pH 5 to 9. A molecular simulation and quantum mechanics analysis indicated that the formation of an amide bond played a crucial role in the kokumi-enhancing effect of N-l-Lac-l-Met, specifically by increasing its affinity with umami receptors T1R1-T1R3 and a kokumi receptor CaSR. These findings established the relationship between amide bond formation and the kokumi-enhancing effect of N-l-Lac-l-Met, presenting its potential application as the kokumi substance in the food industry.
Keywords: N-l-lactoyl-l-Met; amide bonds; enzymatically synthesized; kokumi; molecular simulation.