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[Peptide Foldamers: Structural Control and Cell-penetrating Ability].

Makoto Oba1

  • 1Graduate School of Biomedical Sciences, Nagasaki University.

Yakugaku Zasshi : Journal of the Pharmaceutical Society of Japan
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Summary

Alpha,alpha-Disubstituted alpha-amino acids (dAAs) stabilize peptide structures. Novel cyclic dAAs with acetal side chains enable tunable peptide conformations, leading to applications in cell-penetrating peptide foldamers for efficient biomacromolecule delivery.

Keywords:
cell-penetrating peptidefoldamerhelical structurepeptideunnatural amino acid

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Area of Science:

  • Biochemistry
  • Organic Chemistry
  • Materials Science

Background:

  • Alpha,alpha-disubstituted alpha-amino acids (dAAs) are key building blocks for peptide foldamers, influencing peptide secondary structures.
  • Acyclic dAAs with bulky substituents favor planar conformations, while cyclic dAAs promote helical structures.

Purpose of the Study:

  • To develop a novel methodology for controlling peptide conformation using cyclic dAAs.
  • To explore the application of dAA-based peptide foldamers in functional peptides, particularly for drug delivery.

Main Methods:

  • Utilized cyclic dAAs with acetal side chains to induce conformational changes in peptides.
  • Investigated the conformational properties of peptides containing various dAAs.
  • Designed and evaluated cell-penetrating peptide foldamers for biomacromolecule delivery.

Main Results:

  • Developed a method to switch peptide structures from helical to random conformations using acidic treatment.
  • Demonstrated that dAA-containing peptide foldamers exhibit protease resistance.
  • Achieved efficient cell membrane permeability and intracellular delivery of biomacromolecules using designed peptide foldamers.

Conclusions:

  • Cyclic dAAs offer a versatile tool for designing conformationally controlled peptide foldamers.
  • dAA-based peptide foldamers show promise for developing protease-resistant bioactive peptides.
  • Cell-penetrating peptide foldamers derived from dAAs are effective for delivering biomacromolecules into cells.