ArticleNature communications2015
New peptide architectures through C-H activation stapling between tryptophan-phenylalanine/tyrosine residues.
Article in Nature communications, 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 63 papers.
What it found
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Who cites it
63 citing papers in PubMed.
- Functionalization of Peptides via Radical Arylation.Chembiochem : a European journal of chemical biology · 2026Review
- Bis-Tetrazine Fluorogenic (Silicon)-Rhodamine Dyes for Live-Cell Labeling.Journal of the American Chemical Society · 2026Article
- Unified Access to Biaryl-Bridged Linkages Unlocks Structural Diversification of Noncanonical Cyclic Peptides.Journal of the American Chemical Society · 2026Article
- Making Blank Faces Expressive: Chemical Approaches to the Modification of Chemically Inert Peptides.Journal of peptide science : an official publication of the European Peptide Society · 2026Review
- Chemoselective, regioselective, and positionally selective fluorogenic stapling of unprotected peptides for cellular uptake and direct cell imaging.Chemical science · 2025Article
- Empowering canonical biochemicals with cross-linked novelty: Recursions in applications of protein cross-links.Proteins · 2025Review
- Ideas Behind the Tryptophan-Mediated Petasis Reaction (TMPR) Concept for Peptide Stapling.ChemMedChem · 2024Review
- Overcoming Pd Catalyst Deactivation in the C-H Coupling of Tryptophan Residues in Water Using Air as the Oxidant.ACS catalysis · 2024Article
- Non-symmetric stapling of native peptides.Nature reviews. Chemistry · 2024Review
- Applications of biaryl cyclization in the synthesis of cyclic enkephalin analogs with a highly restricted flexibility.Amino acids · 2024Article
- Synthesis of Fluorescent Cyclic Peptides via Gold(I)-Catalyzed Macrocyclization.Journal of the American Chemical Society · 2023Article
- Chemoselective Late-Stage Functionalization of Peptides via Photocatalytic C2-Alkylation of Tryptophan.Organic letters · 2023Article
- Modular synthesis of clickable peptides via late-stage maleimidation on C(7)-H tryptophan.Nature communications · 2023Article
- Transition-Metal-Catalyzed C-H Bond Activation for the Formation of C-C Bonds in Complex Molecules.Chemical reviews · 2023Review
- Facilitating the structural characterisation of non-canonical amino acids in biomolecular NMR.Magnetic resonance (Gottingen, Germany) · 2023Article
- Selective editing of a peptide skeletonChemical science · 2022Article
- Recent Synthesis, Characterization, and Pharmacological Evaluation of Multifunctional Hemorphins Containing Non-Natural Amino Acids with Potential Biological Importance.Pharmaceuticals (Basel, Switzerland) · 2022Review
- Biocompatible and Selective Generation of Bicyclic Peptides.Angewandte Chemie (International ed. in English) · 2022Article
- Cytochrome P450Angewandte Chemie (International ed. in English) · 2022Article
- Opportunities for Expanding Encoded Chemical Diversification and Improving Hit Enrichment in mRNA-Displayed Peptide Libraries.Chembiochem : a European journal of chemical biology · 2022Review
3 more citing papers are in PubMed but not listed here.
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Authors and funding
7 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Natural peptides show high degrees of specificity in their biological action. However, their therapeutical profile is severely limited by their conformational freedom and metabolic instability. Stapled peptides constitute a solution to these problems and access to these structures lies on a limited number of reactions involving the use of non-natural amino acids. Here, we describe a synthetic strategy for the preparation of unique constrained peptides featuring a covalent bond between tryptophan and phenylalanine or tyrosine residues. The preparation of such peptides is achieved in solution and on solid phase directly from the corresponding sequences having an iodo-aryl amino acid through an intramolecular palladium-catalysed C-H activation process. Moreover, complex topologies arise from the internal stapling of cyclopeptides and double intramolecular arylations within a linear peptide. Finally, as a proof of principle, we report the application to this new stapling method to relevant biologically active compounds.
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