ArticleJournal of the American Chemical Society2019
Versatile Peptide Macrocyclization with Diels-Alder Cycloadditions.
Article in Journal of the American Chemical Society, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 18 papers.
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Who cites it
18 citing papers in PubMed.
- Date Palm Pollen (Molecules (Basel, Switzerland) · 2026Article
- The Potential of Peptide-Based Inhibitors in Disrupting Protein-Protein Interactions for Targeted Cancer Therapy.International journal of molecular sciences · 2025Review
- Applications of Diels-Alder Chemistry in Biomaterials and Drug Delivery.Macromolecular bioscience · 2024Review
- Tackling Undruggable Targets with Designer Peptidomimetics and Synthetic Biologics.Chemical reviews · 2024Review
- Facile Peptide Macrocyclization and Multifunctionalization via Cyclen Installation.Small methods · 2024Article
- Recent Advances in Metal-Free Peptide Stapling Strategies.Chem & bio engineering · 2024Review
- Proximity-Induced Ligation and One-Pot Macrocyclization of 1,4-Diketone-Tagged Peptides Derived from 2,5-Disubstituted Furans upon Release from the Solid Support.Organic letters · 2023Article
- Identification of macrocyclic peptides which activate bacterial cylindrical proteases.RSC medicinal chemistry · 2023Article
- Differential Peptide Multi-Macrocyclizations at the Surface of a Helical Foldamer Template.Angewandte Chemie (International ed. in English) · 2022Article
- Convenient synthesis of dipeptide structures in solution phase assisted by a thioaza functionalized magnetic nanocatalyst.Scientific reports · 2022Article
- Protease-Resistant Peptides for Targeting and Intracellular Delivery of Therapeutics.Pharmaceutics · 2021Review
- Solid-Phase Peptide Macrocyclization and Multifunctionalization via Dipyrrin Construction.Angewandte Chemie (International ed. in English) · 2021Article
- Cys-Cys and Cys-Lys Stapling of Unprotected Peptides Enabled by Hypervalent Iodine Reagents.Angewandte Chemie (International ed. in English) · 2021Article
- Adaptive Evolution of Peptide Inhibitors for Mutating SARS-CoV-2.Advanced theory and simulations · 2020Article
- On-Demand Detachment of Succinimides on Cysteine to Facilitate (Semi)Synthesis of Challenging Proteins.Journal of the American Chemical Society · 2020Article
- Adaptive Evolution of Peptide Inhibitors for Mutating SARS-CoV-2.ChemRxiv : the preprint server for chemistry · 2020Article
- Applications of Thiol-Ene Chemistry for Peptide Science.Frontiers in chemistry · 2020Review
- Bent Into Shape: Folded Peptides to Mimic Protein Structure and Modulate Protein Function.Peptide science (Hoboken, N.J.) · 2020Article
Corrections and comments
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Authors and funding
8 authors.
Funding
Abstract
Macrocyclization can improve bioactive peptide ligands through preorganization of molecular topology, leading to improvement of pharmacologic properties like binding affinity, cell permeability, and metabolic stability. Here we demonstrate that Diels-Alder [4 + 2] cycloadditions can be harnessed for peptide macrocyclization and stabilization within a range of peptide scaffolds and chemical environments. Diels-Alder cyclization of diverse diene-dienophile reactive pairs proceeds rapidly, in high yield and with tunable stereochemical preferences on solid-phase or in aqueous solution. This reaction can be applied alone or in concert with other stabilization chemistries, such as ring-closing olefin metathesis, to stabilize loop, turn, and α-helical secondary structural motifs. NMR and molecular dynamics studies of model loop peptides confirmed preferential formation of
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