ArticleProceedings of the National Academy of Sciences of the United States of America2013
Template-constrained macrocyclic peptides prepared from native, unprotected precursors.
Article in Proceedings of the National Academy of Sciences of the United States of America, 2013. 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.
- Synthesis of Membrane-Permeable Macrocyclic Peptides via Imidazopyridinium Grafting.Journal of the American Chemical Society · 2024Article
- Extendable stapling of unprotected peptides by crosslinking two amines with o-phthalaldehyde.Nature communications · 2022Article
- Macrocyclization strategies for cyclic peptides and peptidomimetics.RSC medicinal chemistry · 2021Review
- Streamlined construction of peptide macrocyclesChemical science · 2021Article
- Computational generation of an annotated gigalibrary of synthesizable, composite peptidic macrocycles.Proceedings of the National Academy of Sciences of the United States of America · 2020Article
- Synthesis of 9-Dechlorochrysophaentin A Enables Studies Revealing Bacterial Cell Wall Biosynthesis Inhibition Phenotype inJournal of the American Chemical Society · 2020Article
- Adapting free energy perturbation simulations for large macrocyclic ligands: how to dissect contributions from direct binding and free ligand flexibility.Chemical science · 2020Article
- Photoredox Ni-catalyzed peptide C(spChemical science · 2019Article
- A general strategy for synthesis of cyclophane-braced peptide macrocycles via palladium-catalysed intramolecular spNature chemistry · 2018Article
- Synthetic fermentation of β-peptide macrocycles by thiadiazole-forming ring-closing reactions.Chemical science · 2018Article
- Cyclic Peptides that Govern Signal Transduction Pathways: From Prokaryotes to Multi-Cellular Organisms.Current topics in medicinal chemistry · 2018Review
- Peptide Macrocyclization Inspired by Non-Ribosomal Imine Natural Products.Journal of the American Chemical Society · 2017Article
- Diversity of Secondary Structure in Catalytic Peptides with β-Turn-Biased Sequences.Journal of the American Chemical Society · 2017Article
- 4R- and 4S-iodophenyl hydroxyproline, 4R-pentynoyl hydroxyproline, and S-propargyl-4-thiolphenylalanine: conformationally biased and tunable amino acids for bioorthogonal reactions.Organic & biomolecular chemistry · 2016Article
- Bridged bicyclic peptides as potential drug scaffolds: synthesis, structure, protein binding and stability.Chemical science · 2015Article
- New peptide architectures through C-H activation stapling between tryptophan-phenylalanine/tyrosine residues.Nature communications · 2015Article
- Large ring-forming alkylations provide facile access to composite macrocycles.Chemical science · 2015Article
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3 authors.
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Abstract
Peptide-protein interactions are important mediators of cellular-signaling events. Consensus binding motifs (also known as short linear motifs) within these contacts underpin molecular recognition, yet have poor pharmacological properties as discrete species. Here, we present methods to transform intact peptides into stable, templated macrocycles. Two simple steps install the template. The key reaction is a palladium-catalyzed macrocyclization. The catalysis has broad scope and efficiently forms large rings by engaging native peptide functionality including phenols, imidazoles, amines, and carboxylic acids without the necessity of protecting groups. The tunable reactivity of the template gives the process special utility. Defined changes in reaction conditions markedly alter chemoselectivity. In all cases examined, cyclization occurs rapidly and in high yield at room temperature, regardless of peptide composition or chain length. We show that conformational restraints imparted by the template stabilize secondary structure and enhance proteolytic stability in vitro. Palladium-catalyzed internal cinnamylation is a strong complement to existing methods for peptide modification.
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