ArticleChemical science2017
A novel peptide stapling strategy enables the retention of ring-closing amino acid side chains for the Wnt/β-catenin signalling pathway.
Article in Chemical science, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 19 papers.
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Who cites it
19 citing papers in PubMed, 56 citations in OpenAlex.
- Unified Access to Biaryl-Bridged Linkages Unlocks Structural Diversification of Noncanonical Cyclic Peptides.Journal of the American Chemical Society · 2026Article
- Systematical Mutational Analysis of FRATtide against Osteoclast Differentiation by Alanine Scanning.ACS medicinal chemistry letters · 2024Article
- Discovery of novel antibacterial agent for the infected wound treatment: all-hydrocarbon stapling optimization of LL-37.Theranostics · 2024Article
- Cyclobutane-bearing restricted anchoring residues enabled geometry-specific hydrocarbon peptide stapling.Chemical science · 2023Article
- Methodology of stable peptide based on propargylated sulfonium.Biochemistry and biophysics reports · 2023Article
- Discovery of an orally effective double-stapled peptide for reducing ovariectomy-induced bone loss in mice.Acta pharmaceutica Sinica. B · 2023Article
- Facilitating the structural characterisation of non-canonical amino acids in biomolecular NMR.Magnetic resonance (Gottingen, Germany) · 2023Article
- Design and synthesis of Nrf2-derived hydrocarbon stapled peptides for the disruption of protein-DNA-interactions.PloS one · 2022Article
- Design, Synthesis and Antifungal Activity of Stapled Aurein1.2 Peptides.Antibiotics (Basel, Switzerland) · 2021Article
- Cysteine [2,4] Disulfide Bond as a New Modifiable Site of α-Conotoxin TxIB.Marine drugs · 2021Article
- Cytotoxic and antitumor peptides as novel chemotherapeutics.Natural product reports · 2021Review
- Chemical synthesis and biological activity of peptides incorporating an ether bridge as a surrogate for a disulfide bond.Chemical science · 2020Article
- Rational design of stapled peptides targeting phosphorylated GSK3β for regulating osteoclast differentiation.RSC advances · 2020Article
- The peptide PROTAC modality: a novel strategy for targeted protein ubiquitination.Theranostics · 2020Review
- Advances in the Study of Structural Modification and Biological Activities of Anoplin.Frontiers in chemistry · 2020Review
- Recognition of ASF1 by Using Hydrocarbon-Constrained Peptides.Chembiochem : a European journal of chemical biology · 2019Article
- Recent structural advances in constrained helical peptides.Medicinal research reviews · 2019Review
- Dithiocarbamate-inspired side chain stapling chemistry for peptide drug design.Chemical science · 2019Article
- Stapling strategy enables improvement of antitumor activity and proteolytic stability of host-defense peptide hymenochirin-1B.RSC advances · 2018Article
Corrections and comments
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Authors and funding
9 authors at 4 institutions in 3 countries.
Funding
No grant is acknowledged in the PubMed record.
Abstract
The all-hydrocarbon peptide stapling strategy has recently been extensively explored in drug discovery. There remains the potential for improvement regarding the retention of the amino acid side chains at the stapled positions. Herein, we describe a new series of amino acids that not only contain the native side chains, but also carry the alkenyl arms that are needed for the ring-closing stapling chemistry. We incorporate the new amino acids into a β-catenin-binding domain of Axin (469-482) and develop a new category of stapled peptides with the retention of the native side chains. These stapled peptides exhibit high α-helicity, strong proteolytic stability and good cell permeability. Biochemical experiments demonstrate that these stapled peptides can activate β-catenin more efficiently than canonical stapled peptides due to the presence of extra side chains. We expect that the new side-chain-retention stapling method would expand the scope of the all-hydrocarbon stapled peptide strategy by retaining some important peripheral residues for protein-protein interactions or preserving key hydrophilic side chains to improve solubility.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.