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Variable-Length Ester-Based Staples for α-Helical Peptides by Using A Double Thiol-ene Reaction.

Danielle L Paterson1,2, Jack U Flanagan1,2,3,4, Peter R Shepherd1,2,3,5

  • 1School of Biological Sciences, The University of Auckland, 3A Symonds Street, Auckland, 1142, New Zealand.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|April 2, 2020
PubMed
Summary

A new peptide stapling technique uses a double thiol-ene reaction to create stapled peptides with better cell permeability. This method enhances alpha-helicity and allows targeting of intracellular proteins.

Keywords:
alpha helicesdivinyl esterspeptidesstaplingthiol-ene reactions

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Area of Science:

  • Medicinal Chemistry
  • Biochemistry
  • Organic Synthesis

Background:

  • Alpha-helical peptides are important for targeting intracellular proteins but often lack cell permeability.
  • Developing methods to enhance peptide stability and cell penetration is crucial for drug discovery.

Purpose of the Study:

  • To report a novel peptide stapling method utilizing a double thiol-ene reaction.
  • To synthesize stapled peptides with enhanced cell permeability and improved alpha-helicity.
  • To demonstrate the utility of this method for targeting intracellular proteins.

Main Methods:

  • A double thiol-ene reaction between cysteine residues and a divinyl diester was employed for peptide stapling.
  • The method allowed for facile synthesis of stapled peptides with varying bridge lengths.
  • Stapled Axin mimetics and SIGK peptide analogues were synthesized and characterized.

Main Results:

  • The novel peptide stapling method successfully produced stapled peptides with enhanced cell permeability.
  • Stapled Axin mimetics showed improved alpha-helicity compared to unstapled versions.
  • Cell-penetrating stapled SIGK peptide analogues exhibited moderate increases in alpha-helicity and were cell permeable.

Conclusions:

  • The reported chemoselective peptide stapling method is a versatile tool for modifying synthetic alpha-helical peptides.
  • This technique facilitates the development of stapled peptides for targeting intracellular protein-protein interactions.
  • The method offers a facile approach to enhance the therapeutic potential of alpha-helical peptides.