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Peptide Bonds

Peptide Bonds

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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Updated: Aug 6, 2025

Constructing Cyclic Peptides Using an On-Tether Sulfonium Center

Constructing Cyclic Peptides Using an On-Tether Sulfonium Center

Published on: September 28, 2022

Constraining and Modifying Peptides Using Pd-Mediated Cysteine Allylation.

Julia Kriegesmann¹, Thomas Schlatzer², Kateryna Che¹

¹Institute of Biological Chemistry, Faculty of Chemistry, University of Vienna, 1090, Vienna, Austria.

Chembiochem : a European Journal of Chemical Biology

|March 14, 2023

Summary

This summary is machine-generated.

Chemoselective Pd-catalyzed allylation enables peptide stapling and further modification. This method enhances peptide stability and allows for the introduction of probes like fluorophores and PEG moieties, improving binding affinity.

Keywords:

Diels-Alder reaction allylation reaction peptide stapling secondary peptide modification

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Synthesis and Structure Determination of µ-Conotoxin PIIIA Isomers with Different Disulfide Connectivities

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Last Updated: Aug 6, 2025

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Synthesis and Structure Determination of µ-Conotoxin PIIIA Isomers with Different Disulfide Connectivities

Synthesis and Structure Determination of µ-Conotoxin PIIIA Isomers with Different Disulfide Connectivities

Published on: October 2, 2018

Area of Science:

Chemical Biology
Medicinal Chemistry
Peptide Chemistry

Background:

Peptide secondary structure stabilization is crucial for proteolytic stability and binding affinity.
Existing methods for peptide stabilization have limitations.

Purpose of the Study:

To extend a chemoselective Pd-catalyzed cysteine allylation reaction for peptide stapling.
To demonstrate further modification of alkene-containing staples with probes.
To investigate the structural impact of allyl staples replacing disulfide bridges.

Main Methods:

Chemoselective Pd-catalyzed cysteine allylation for peptide stapling.
Bioorthogonal thiol-ene and Diels-Alder reactions for probe introduction (fluorophore, PEG).
Structural analysis of stapled peptides replacing disulfide bridges in integrin α3β1 binder (LXY3).

Main Results:

Successful extension of Pd-catalyzed allylation for peptide stapling.
Introduction of fluorophores and PEG moieties via bioorthogonal reactions on stapled peptides.
Demonstrated replacement of disulfide bridges with allyl staples in LXY3, impacting integrin α3β1 binding.

Conclusions:

The developed method offers a versatile platform for creating stabilized peptides with tunable properties.
Allyl staples can effectively replace disulfide bonds, offering potential for enhanced peptide therapeutics.
Further functionalization of staples allows for advanced peptide engineering and diagnostics.