ArticleChembiochem : a European journal of chemical biology2016
Constraining an Irregular Peptide Secondary Structure through Ring-Closing Alkyne Metathesis.
Article in Chembiochem : a European journal of chemical biology, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 17 papers.
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Who cites it
17 citing papers in PubMed.
- Helicity-Dependent Enzymatic Peptide Cyclization.Journal of peptide science : an official publication of the European Peptide Society · 2025Article
- Navigating complex peptide structures using macrocycle conformational maps.RSC chemical biology · 2022Article
- Design and synthesis of Nrf2-derived hydrocarbon stapled peptides for the disruption of protein-DNA-interactions.PloS one · 2022Article
- The Ascent of Alkyne Metathesis to Strategy-Level Status.Journal of the American Chemical Society · 2021Article
- Macrocyclization strategies for cyclic peptides and peptidomimetics.RSC medicinal chemistry · 2021Review
- Identification and confirmation of 14-3-3 ζ as a novel target of ginsenosides in brain tissues.Journal of ginseng research · 2021Article
- Cyclisation strategies for stabilising peptides with irregular conformations.RSC medicinal chemistry · 2021Review
- Impact of Ligands and Metals on the Formation of Metallacyclic Intermediates and a Nontraditional Mechanism for Group VI Alkyne Metathesis Catalysts.Journal of the American Chemical Society · 2021Article
- "Canopy Catalysts" for Alkyne Metathesis: Molybdenum Alkylidyne Complexes with a Tripodal Ligand Framework.Journal of the American Chemical Society · 2020Article
- Formation of alkyne-bridged ferrocenophanes using ring-closing alkyne metathesis on 1,1'-diacetylenic ferrocenes.Beilstein journal of organic chemistry · 2019Article
- On-Resin Macrocyclization of Peptides Using Vinyl Sulfonamides as a Thiol-Michael "Click" Acceptor.Bioconjugate chemistry · 2018Article
- Hydrogen Bond Surrogate Stabilization of β-Hairpins.ACS chemical biology · 2018Article
- 14-3-3: A Case Study in PPI Modulation.Molecules (Basel, Switzerland) · 2018Review
- Modulators of 14-3-3 Protein-Protein Interactions.Journal of medicinal chemistry · 2018Review
- Structure-Based Design of Non-natural Macrocyclic Peptides That Inhibit Protein-Protein Interactions.Journal of medicinal chemistry · 2017Article
- Identification of Two Secondary Ligand Binding Sites in 14-3-3 Proteins Using Fragment Screening.Biochemistry · 2017Article
- Constraining an Irregular Peptide Secondary Structure through Ring-Closing Alkyne Metathesis.Chembiochem : a European journal of chemical biology · 2016Article
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7 authors.
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Abstract
Macrocyclization can be used to constrain peptides in their bioactive conformations, thereby supporting target affinity and bioactivity. In particular, for the targeting of challenging protein-protein interactions, macrocyclic peptides have proven to be very useful. Available approaches focus on the stabilization of α-helices, which limits their general applicability. Here we report for the first time on the use of ring-closing alkyne metathesis for the stabilization of an irregular peptide secondary structure. A small library of alkyne-crosslinked peptides provided a number of derivatives with improved target affinity relative to the linear parent peptide. In addition, we report the crystal structure of the highest-affinity derivative in a complex with its protein target 14-3-3ζ. It can be expected that the alkyne-based macrocyclization of irregular binding epitopes should give rise to new scaffolds suitable for targeting of currently intractable proteins.
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