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Related Concept Videos

Peptide Bonds02:43

Peptide Bonds

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A peptide bond covalently attaches amino acids through a dehydration reaction. One amino acid's carboxyl group and another amino acid's amino group combine, releasing a water molecule. The resulting bond is the peptide bond. The products that such linkages form are peptides. As more amino acids join this growing chain, the resulting chain is a polypeptide. Each polypeptide has a free amino group at one end. This end has the N-terminal, or the amino-terminal, and the other end has a free...
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Constructing Thioether/Vinyl Sulfide-tethered Helical Peptides Via Photo-induced Thiol-ene/yne Hydrothiolation
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Review stapling peptides using cysteine crosslinking.

David P Fairlie1, Aline Dantas de Araujo1

  • 1Institute for Molecular Bioscience, the University of Queensland, Brisbane, QLD, 4072, Australia.

Biopolymers
|May 15, 2016
PubMed
Summary

Stapled peptides, cyclic molecules with improved stability and binding, are synthesized using cysteine-based crosslinking. Recent advances focus on bisthioether macrocycles with diverse properties.

Keywords:
S-alkylationS-arylationchemoselective reactioncysteine conjugationmacrocyclizationpeptide staplingthiol-ene couplingα-helix

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Area of Science:

  • Medicinal Chemistry
  • Biochemistry
  • Peptide Science

Background:

  • Stapled peptides offer enhanced stability, cellular uptake, and target binding compared to linear peptides.
  • Cysteine-based stapling is a key strategy for synthesizing these cyclic peptides due to accessible precursors.

Purpose of the Study:

  • To present recent advancements in peptide and protein stapling techniques.
  • To explore the synthesis and properties of bisthioether macrocyclic peptides using cysteine crosslinking.

Main Methods:

  • Utilizing cysteine residues for covalent crosslinking of peptide side-chains.
  • Employing a variety of crosslinkers to form macrocyclic structures.
  • Synthesizing bisthioether macrocyclic peptides with diverse topologies.

Main Results:

  • Demonstrated successful synthesis of macrocyclic peptides via cysteine-based stapling.
  • Showcased the formation of bisthioether linkages with various crosslinkers.
  • Highlighted the resulting peptides' varied topological and biophysical properties.

Conclusions:

  • Cysteine-based stapling provides a versatile method for creating stapled peptides.
  • This approach yields bisthioether macrocyclic peptides with tunable properties.
  • Advancements in stapling chemistry expand the potential of peptide therapeutics.