Preparation, Sensory Characterization, and Umami-Enhancing Mechanism of Novel Peptide Glycoconjugates

N-Lactoyl-amino acid derivatives (N-Lac-AAs) are of increasing interest as potential taste-active compounds. The complexity and diversity of N-Lac-AAs pose a significant challenge to the effective discovery of taste-active N-Lac-AAs. Therefore, a structure-based virtual screening was used to identify taste-active N-Lac-AAs. Virtual screening results showed that N-lactoylhydrophobic amino acids had a higher affinity for taste receptors, specifically N-L-Lac-L-Trp. And then, N-L-Lac-L-Trp was synthesized in yields of 22.3% by enzymatic synthesis in the presence of L-lactate and L-Trp, and its chemical structure was confirmed by MS/MS and one-dimensional (1D) and two-dimensional (2D) NMR. Sensory evaluation revealed that N-L-Lac-L-Trp had a significant taste-masking effect on quinine, D-salicin, caffeine, and L-Trp, particularly L-Trp and caffeine. N-L-Lac-L-Trp had a better masking effect on the higher concentration of bitter compounds. It reduced the bitterness of caffeine (500 mg/L) and L-Trp (1000 mg/L) by approximately 20 and 26%, respectively. The result of the ligand−receptor interaction and a quantum mechanical analysis showed that N-L-Lac-L-Trp increased the binding affinity to the bitter receptor mainly through hydrogen bonding and lowering the electrostatic potential.

Section: Resultsmentioning

confidence: 99%

Section: Bitterness-masking Effects Of N-l-lac-l-trpmentioning

confidence: 99%

Discovery of N-l-Lactoyl-l-Trp as a Bitterness Masker via Structure-Based Virtual Screening and a Sensory Approach

Zhao

Zhou

Cui

et al. 2023

“…The increases in sour and astringency may have been due to residual amino acids and sodium acetate from the peptide synthesis process . There may be differences in sensory between synthetic peptides and naturally extracted umami peptides . ERRY was more noticeable in the umami character when sensory evaluation and electronic tongue data were combined.…”

Section: Resultsmentioning

confidence: 98%

“…28 There may be differences in sensory between synthetic peptides and naturally extracted umami peptides. 29 ERRY was more noticeable in the umami character when sensory evaluation and electronic tongue data were combined.…”

Section: Purification Of Umami Fractions In Sturgeon Dorsalmentioning

confidence: 94%

Identification and Verification of Novel Umami Peptides Isolated from Hybrid Sturgeon Meat (Acipenser baerii × Acipenser schrenckii)

Wang,

Han,

Zhao

et al. 2023

To explore the umami mechanism in sturgeon meat, five peptides (ERRY, VRGPR, LKYPLE, VKKVFK, and YVVFKD) were isolated and identified by ultrafiltration, gel filtration chromatography, and UPLC-QTOF-MS/MS. The omission test confirmed that the five umami peptides contributed to the umami taste of sturgeon meat. Also, the peptides had the double effective role of enhancing both umami and saltiness. The threshold of ERRY was only 0.031, which exceeded most umami peptides in the last 3 years. Molecular docking results showed that five peptides could easily bind to Gly167, Ser170, and Try218 residues in T1R3 through hydrogen bonds and electrostatic interactions. Furthermore, molecular dynamics simulations indicated that hydrogen bonds and hydrophobic interactions were the main intermolecular interaction forces. This study could contribute to revealing the umami taste mechanism of sturgeon meat and provide new insights for effective screening of short umami peptides.

“…The preparation and characterization of MRIs derived from the model systems consisting of diverse amino acids (or peptides) and reducing sugars have been widely reported. , The formation time of ARPs and other intermediates can be indicated by the browning-inhibited effect of tracers such as cysteine in a simple model reaction system, thus assisting in the preparation and application of MRIs. , Moreover, for those simple model systems, the process of the Maillard reaction could be inferred by monitoring the substrate peptides or amino acids and sugars during the Maillard reaction. ARPs and their degradation products, such as α-dicarbonyl compounds and other intermediates, can also be isolated, purified, and quantified, which would help us to infer the process of Maillard reaction .…”

Section: Introductionmentioning

confidence: 99%

Maillard Reaction Process and Characteristic Volatile Compounds Formed During Secondary Thermal Degradation Monitored via the Change of Fluorescent Compounds in the Reaction of Xylose–Corn Protein Hydrolysate

Li,

Yao,

Xia

et al. 2023

Self Cite

Until now, no effective method has been found to monitor the Maillard reaction process for complex protein hydrolysates. Dynamic changes in the concentration of α-dicarbonyl compounds, fluorescence intensity, and browning degree were investigated during the Maillard reaction of corn protein hydrolysates. When the fluorescence intensity reached the peak, deoxyosones would continue to be increased by ARP's degradation. However, the reaction node with the highest fluorescence intensity coincided with the turning point of the browning reaction, and the subsequent browning rate remarkably increased. Therefore, the change in fluorescence intensity could be used to monitor the degradation of ARP and the formation of browning melanoidin at different stages of the Maillard reaction of complex systems, thus effectively indicating the process of the Maillard reaction. When Maillard reaction intermediates (MRIs) with maximum fluorescent compounds were heated, the most abundant pyrazines were subsequently achieved. However, furan compounds would be progressively increased during the thermal process of MRIs with continuously enhanced browning.