ArticleChembiochem : a European journal of chemical biology2018
Rigid Peptide Macrocycles from On-Resin Glaser Stapling.
Article in Chembiochem : a European journal of chemical biology, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 12 papers.
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Who cites it
12 citing papers in PubMed, 33 citations in OpenAlex.
- Unified Access to Biaryl-Bridged Linkages Unlocks Structural Diversification of Noncanonical Cyclic Peptides.Journal of the American Chemical Society · 2026Article
- Chemoselective, regioselective, and positionally selective fluorogenic stapling of unprotected peptides for cellular uptake and direct cell imaging.Chemical science · 2025Article
- A survey of stapling methods to increase affinity, activity, and stability of ghrelin analogues.RSC medicinal chemistry · 2024Article
- Development of Bifunctional, Raman Active Diyne-Girder Stapled α-Helical Peptides.Chemistry (Weinheim an der Bergstrasse, Germany) · 2023Article
- Stretching Peptides to Generate Small Molecule β-Strand Mimics.ACS central science · 2023Article
- Macrocyclization strategies for cyclic peptides and peptidomimetics.RSC medicinal chemistry · 2021Review
- Long-range PEG Stapling: Macrocyclization for Increased Protein Conformational Stability and Resistance to Proteolysis.RSC chemical biology · 2020Article
- Constrained Peptides with Fine-Tuned Flexibility Inhibit NF-Y Transcription Factor Assembly.Angewandte Chemie (International ed. in English) · 2019Article
- Stereoisomerism of stapled peptide inhibitors of the p53-Mdm2 interaction: an assessment of synthetic strategies and activity profiles.Chemical science · 2019Article
- Recent structural advances in constrained helical peptides.Medicinal research reviews · 2019Review
- On-Resin Macrocyclization of Peptides Using Vinyl Sulfonamides as a Thiol-Michael "Click" Acceptor.Bioconjugate chemistry · 2018Article
- Pyrrole-Mediated Peptide Cyclization Identified through Genetically Reprogrammed Peptide Synthesis.Biomedicines · 2018Article
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Authors and funding
4 authors at 1 institution in 1 country.
Funding
Abstract
Peptide macrocycles are widely utilized in the development of high affinity ligands, including stapled α-helices. The linear rigidity of a 1,3-diynyl linkage provides an optimal distance (7 Å) between β-carbons of the i,i+4 amino acid side chains, thus suggesting its utility in stabilizing α-helical structures. Here, we report the development of an on-resin strategy for an intramolecular Glaser reaction between two alkyne-terminated side chains by using copper chloride, an essential bpy-diol ligand, and diisopropylethylamine at room temperature. The efficiency of this ligation was illustrated by the synthesis of (i,i+4)-, (i,i+5)-, (i,i+6)-, and (i,i+7)-stapled BCL-9 α-helical peptides using the unnatural amino acid propargyl serine. Overall, this procedurally simple method relies on inexpensive and widely available reagents to generate low molecular weight 23-, 26-, 29-, and 32-membered peptide macrocycles.
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