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Cyclization: A potential effective modification strategy for umami peptides.

Zhiyong Cui1, Yanyang Yu1, Tianxing Zhou2

  • 1Department of Food Science & Technology, School of Agriculture & Biology, Shanghai Jiao Tong University, Shanghai 200240, PR China.

Food Chemistry
|December 25, 2024
PubMed
Summary
This summary is machine-generated.

Cyclizing taste peptides enhances their properties, with head-to-tail cyclization significantly boosting umami intensity. This novel strategy offers a new approach for developing improved umami peptide ingredients.

Keywords:
CyclizationElectrostatic rearrangementRecognition thresholdUmami peptide

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Area of Science:

  • Food Science
  • Biochemistry
  • Molecular Biology

Background:

  • Peptide cyclization is a known method to enhance molecular properties in life sciences.
  • However, its application to taste peptides, specifically for enhancing umami taste, remains unexplored.
  • This study introduces the concept of cyclic umami peptides.

Purpose of the Study:

  • To investigate the effect of N/C-terminal (head-to-tail) cyclization on the properties of umami peptides.
  • To explore cyclization as a modification strategy for improving umami peptide characteristics.
  • To report the first instance of umami cyclic peptides.

Main Methods:

  • Umami peptides were sourced from TastePeptidesDB and their linear/cyclic structures were modeled.
  • Molecular docking was performed with umami receptors, followed by contact matrix analysis and clustering.
  • Chemically synthesized peptides underwent sensory evaluation, molecular fingerprint analysis, and Density Functional Theory (DFT) calculations.

Main Results:

  • Cyclization significantly increased the umami intensity and decreased the recognition threshold of the peptide DPLRGGY.
  • Conversely, the umami intensity of RGEPNND decreased upon cyclization.
  • Correlation was found between polarity, threshold differences, and electrostatic rearrangement, explaining the observed changes in umami intensity.

Conclusions:

  • Head-to-tail cyclization via an amide bond is a viable strategy for enhancing umami peptide properties.
  • Electrostatic rearrangement resulting from cyclization is the primary driver for altered umami intensity.
  • This research provides a novel approach for developing and optimizing umami peptide derivatives.