ArticleJournal of the American Chemical Society2014
Z-Selective olefin metathesis on peptides: investigation of side-chain influence, preorganization, and guidelines in substrate selection.
Article in Journal of the American Chemical Society, 2014. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 15 papers.
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Who cites it
15 citing papers in PubMed.
- Triazole-modified Ru-carbene complexes: A valid olefin metathesis pre-catalyst for dynamic covalent chemistry via C=C bond formation.Chem catalysis · 2023Article
- Catalysis with cycloruthenated complexes.Chemical science · 2022Review
- Solid-Phase Peptide Macrocyclization and Multifunctionalization via Dipyrrin Construction.Angewandte Chemie (International ed. in English) · 2021Article
- Macrocyclization strategies for cyclic peptides and peptidomimetics.RSC medicinal chemistry · 2021Review
- X-ray Crystallographic Structure of α-Helical Peptide Stabilized by Hydrocarbon Stapling atInternational journal of molecular sciences · 2021Article
- Design and Synthesis of HelicalMolecules (Basel, Switzerland) · 2020Article
- Peptidomimetics prepared by tail-to-side chain one component peptide stapling inhibit Alzheimer's amyloid-β fibrillogenesis.Chemical science · 2020Article
- Optimized Ring Closing Metathesis Reaction Conditions To Suppress Desallyl Side Products in the Solid-Phase Synthesis of Cyclic Peptides Involving Tyrosine(The Journal of organic chemistry · 2020Article
- Stereoisomerism of stapled peptide inhibitors of the p53-Mdm2 interaction: an assessment of synthetic strategies and activity profiles.Chemical science · 2019Article
- Mechanism of Olefin Metathesis with Neutral and Cationic Molybdenum Imido Alkylidene N-Heterocyclic Carbene Complexes.Journal of the American Chemical Society · 2019Article
- Recent advances in ruthenium-based olefin metathesis.Chemical Society reviews · 2018Review
- Cationic ruthenium alkylidene catalysts bearing phosphine ligands.Dalton transactions (Cambridge, England : 2003) · 2016Article
- Stereoselective synthesis of macrocyclic peptides via a dual olefin metathesis and ethenolysis approach.Chemical science · 2015Article
- Z-Selective Olefin Synthesis via Iron-Catalyzed Reductive Coupling of Alkyl Halides with Terminal Arylalkynes.Journal of the American Chemical Society · 2015Article
- Exo-selective reductive macrocyclization of ynals.Organic letters · 2015Article
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Authors and funding
3 authors.
Funding
Abstract
Olefin metathesis has emerged as a promising strategy for modulating the stability and activity of biologically relevant compounds; however, the ability to control olefin geometry in the product remains a challenge. Recent advances in the design of cyclometalated ruthenium catalysts has led to new strategies for achieving such control with high fidelity and Z selectivity, but the scope and limitations of these catalysts on substrates bearing multiple functionalities, including peptides, remained unexplored. Herein, we report an assessment of various factors that contribute to both productive and nonproductive Z-selective metathesis on peptides. The influence of sterics, side-chain identity, and preorganization through peptide secondary structure are explored by homodimerization, cross metathesis, and ring-closing metathesis. Our results indicate that the amino acid side chain and identity of the olefin profoundly influence the activity of cyclometalated ruthenium catalysts in Z-selective metathesis. The criteria set forth for achieving high conversion and Z selectivity are highlighted by cross metathesis and ring-closing metathesis on diverse peptide substrates. The principles outlined in this report are important not only for expanding the scope of Z-selective olefin metathesis to peptides but also for applying stereoselective olefin metathesis in general synthetic endeavors.
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