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Updated: May 8, 2026
07:11
Constructing Cyclic Peptides Using an On-Tether Sulfonium Center
Published on: September 28, 2022
Monosubstituted alkenyl amino acids for peptide "stapling"
David J Yeo1, Stuart L Warriner, Andrew J Wilson
1School of Chemistry, University of Leeds, Woodhouse Lane, Leeds LS2 9JT, UK. A.J.Wilson@leeds.ac.uk.
Chemical Communications (Cambridge, England)
|September 6, 2013
Summary
Alkenylglycine amino acids effectively stabilize peptides through hydrocarbon stapling. This method was successfully applied to the BID BH3 peptide, demonstrating its potential for therapeutic applications.
Area of Science:
- Biochemistry
- Peptide Chemistry
- Drug Discovery
Background:
- Hydrocarbon stapling is a technique used to stabilize peptide structures.
- The BID BH3 peptide plays a role in apoptosis and is a target for drug development.
Purpose of the Study:
- To evaluate alkenylglycine amino acids as novel stapling agents for peptides.
- To assess the efficacy of hydrocarbon stapling on the BID BH3 peptide.
Main Methods:
- Synthesis and incorporation of alkenylglycine amino acids into peptide sequences.
- Hydrocarbon stapling reactions to create cross-links within the peptide.
Main Results:
- Alkenylglycine amino acids were confirmed as effective stapling agents.
- Successful hydrocarbon stapling of the BID BH3 peptide was achieved.
Conclusions:
- Alkenylglycine amino acids represent a viable strategy for peptide stabilization via hydrocarbon stapling.
- This approach holds promise for developing stabilized peptide therapeutics, including for the BID BH3 target.
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