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Double quick, double click reversible peptide "stapling".

Claire M Grison1,2, George M Burslem1,2, Jennifer A Miles1,2

  • 1School of Chemistry , University of Leeds , Woodhouse Lane , Leeds LS2 9JT , UK .

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|October 4, 2017
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Summary
This summary is machine-generated.

This study presents a new, reversible method to stabilize peptides in a helical shape using a dibromomaleimide linker. This peptide stapling technique enhances biological activity and allows for further functionalization, advancing drug discovery.

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Area of Science:

  • Chemical Biology
  • Drug Discovery
  • Peptide Chemistry

Background:

  • Constrained peptides are crucial for inhibiting protein-protein interactions.
  • Developing versatile and reversible peptide stabilization methods is essential for chemical biology and drug discovery.

Purpose of the Study:

  • To introduce a novel, rapid, and reversible method for constraining peptides into bioactive helical conformations.
  • To demonstrate the utility of this method using BID and RNase S peptides as models.

Main Methods:

  • Utilizing dibromomaleimide for double substitution of cysteine (Cys) or homocysteine (hCys) residues at i and i+4 positions.
  • Employing circular dichroism and molecular dynamics simulations to assess helical conformation.
  • Conducting trypsin proteolysis experiments to evaluate proteolytic resistance.
  • Performing functional assays for protein-protein interaction inhibition (BID) and enzyme activity restoration (RNase S peptide).
  • Exploring further functionalization via alkyne-azide cycloaddition chemistry.

Main Results:

  • Achieved enhanced alpha-helical conformation in BID and RNase S peptides.
  • Demonstrated increased resistance to proteolysis for BID peptides.
  • Showcased retained or enhanced inhibitory potency for Bcl-2 family protein-protein interactions.
  • Confirmed greater capability to restore hydrolytic activity for RNase S peptides.
  • Successfully functionalized constrained peptides with fluorescein, oligoethylene glycol, and biotin.

Conclusions:

  • The developed dibromomaleimide-based peptide stapling is a versatile, rapid, and reversible methodology.
  • This approach enhances peptide stability, biological activity, and allows for diverse functionalization.
  • The methodology holds potential to broaden the scope and accessibility of peptide stapling in chemical biology and drug discovery.