ArticleAngewandte Chemie (International ed. in English)2021
Cys-Cys and Cys-Lys Stapling of Unprotected Peptides Enabled by Hypervalent Iodine Reagents.
Article in Angewandte Chemie (International ed. in English), 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 20 papers.
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Who cites it
20 citing papers in PubMed.
- Cys-Lys stapling for unprotected peptides via tunable linkers.National science review · 2025Article
- Peptide/Protein Functionalization and Macrocyclization via Alkyne Umpolung with Hypervalent Iodine Reagents.Accounts of chemical research · 2025Article
- Chemoselective, regioselective, and positionally selective fluorogenic stapling of unprotected peptides for cellular uptake and direct cell imaging.Chemical science · 2025Article
- Facile Peptide Macrocyclization and Multifunctionalization via Cyclen Installation.Small methods · 2024Article
- Recent Progress in Synthetic Applications of Hypervalent Iodine(III) Reagents.Chemical reviews · 2024Review
- Recent Advances in Metal-Free Peptide Stapling Strategies.Chem & bio engineering · 2024Review
- Cysteine-Specific Multifaceted Bioconjugation of Peptides and Proteins Using 5-Substituted 1,2,3-Triazines.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2024Article
- Non-symmetric stapling of native peptides.Nature reviews. Chemistry · 2024Review
- Genetically encoded discovery of perfluoroaryl macrocycles that bind to albumin and exhibit extended circulation in vivo.Nature communications · 2023Article
- Modulating the folding and binding of peptides using a stimuli-responsive molecular tweezer.Chemical science · 2023Article
- A Cysteine-Directed Proximity-Driven Crosslinking Method for Native Peptide Bicyclization.Angewandte Chemie (International ed. in English) · 2023Article
- Recent progress in alkynylation with hypervalent iodine reagents.Chemical communications (Cambridge, England) · 2023Review
- Differential Peptide Multi-Macrocyclizations at the Surface of a Helical Foldamer Template.Angewandte Chemie (International ed. in English) · 2022Article
- An Orthogonal Dynamic Covalent Chemistry Tool for Ring-Opening Polymerization of Cyclic Oligochalcogenides on Detachable Helical Peptide Templates.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Article
- Fast and Cysteine-Specific Modification of Peptides, Proteins and Bacteriophage Using Chlorooximes.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Article
- Hypervalent Iodine-Mediated Late-Stage Peptide and Protein Functionalization.Angewandte Chemie (International ed. in English) · 2022Review
- Peptide stapling by late-stage Suzuki-Miyaura cross-coupling.Beilstein journal of organic chemistry · 2022Article
- Solid-Phase Peptide Macrocyclization and Multifunctionalization via Dipyrrin Construction.Angewandte Chemie (International ed. in English) · 2021Article
- Bioorthogonal Azide-Thioalkyne Cycloaddition Catalyzed by Photoactivatable Ruthenium(II) Complexes.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
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Authors and funding
5 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Easy access to a wide range of structurally diverse stapled peptides is crucial for the development of inhibitors of protein-protein interactions. Herein, we report bis-functional hypervalent iodine reagents for two-component cysteine-cysteine and cysteine-lysine stapling yielding structurally diverse thioalkyne linkers. This stapling method works with unprotected natural amino acid residues and does not require pre-functionalization or metal catalysis. The products are stable to purification and isolation. Post-stapling modification can be accessed via amidation of an activated ester, or via cycloaddition onto the formed thioalkyne group. Increased helicity and binding affinity to MDM2 was obtained for a i,i+7 stapled peptide.
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