ArticleOrganic & biomolecular chemistry2014
Convergent diversity-oriented side-chain macrocyclization scan for unprotected polypeptides.
Article in Organic & biomolecular chemistry, 2014. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 25 papers.
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Who cites it
25 citing papers in PubMed.
- Organometallic Chemistry Approach to Peptide Tricycles.Bioconjugate chemistry · 2026Article
- Fluorescent cationic fluorinated oxazoliniums for cysteine bioconjugationRSC chemical biology · 2026Article
- Advances in Targeted Autophagy Modulation Strategies to Treat Cancer and Associated Treatment-Induced Cardiotoxicity.Pharmaceuticals (Basel, Switzerland) · 2025Review
- Biocompatible strategies for peptide macrocyclisation.Chemical science · 2024Review
- Rational design of stapled antimicrobial peptides.Amino acids · 2023Review
- Discovery of Cyclic Peptide Inhibitors Targeting PD-L1 for Cancer Immunotherapy.Journal of medicinal chemistry · 2022Article
- Perfluoroaryl and Perfluoroheteroaryl Reagents as Emerging New Tools for Peptide Synthesis, Modification and Bioconjugation.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Review
- Macrocyclization strategies for cyclic peptides and peptidomimetics.RSC medicinal chemistry · 2021Review
- Genetically-encoded discovery of proteolytically stable bicyclic inhibitors for morphogen NODAL.Chemical science · 2021Article
- Small and Simple, yet Sturdy: Conformationally Constrained Peptides with Remarkable Properties.International journal of molecular sciences · 2021Review
- Stapled Peptide Inhibitors of Autophagy Adapter LC3B.Chembiochem : a European journal of chemical biology · 2020Article
- Arylation Chemistry for Bioconjugation.Angewandte Chemie (International ed. in English) · 2019Review
- Structure of HIV TAR in complex with a Lab-Evolved RRM provides insight into duplex RNA recognition and synthesis of a constrained peptide that impairs transcription.Nucleic acids research · 2018Article
- Perfluoroaryl Bicyclic Cell-Penetrating Peptides for Delivery of Antisense Oligonucleotides.Angewandte Chemie (International ed. in English) · 2018Article
- Thioether-stapled macrocyclic inhibitors of the EH domain of EHD1.Bioorganic & medicinal chemistry · 2018Article
- Perfluorophenyl Derivatives as Unsymmetrical Linkers for Solid Phase Conjugation.Frontiers in chemistry · 2018Article
- Perfluoroarene-Based Peptide Macrocycles to Enhance Penetration Across the Blood-Brain Barrier.Journal of the American Chemical Society · 2017Article
- Diversity-Oriented Stapling Yields Intrinsically Cell-Penetrant Inducers of Autophagy.Journal of the American Chemical Society · 2017Article
- Divergent unprotected peptide macrocyclisation by palladium-mediated cysteine arylation.Chemical science · 2017Article
- Rapid biocompatible macrocyclization of peptides with decafluoro-diphenylsulfone.Chemical science · 2016Article
Corrections and comments
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Authors and funding
7 authors.
Funding
Abstract
Here we describe a general synthetic platform for side-chain macrocyclization of an unprotected peptide library based on the SNAr reaction between cysteine thiolates and a new generation of highly reactive perfluoroaromatic small molecule linkers. This strategy enabled us to simultaneously "scan" two cysteine residues positioned from i, i + 1 to i, i + 14 sites in a polypeptide, producing 98 macrocyclic products from reactions of 14 peptides with 7 linkers. A complementary reverse strategy was developed; cysteine residues within the polypeptide were first modified with non-bridging perfluoroaryl moieties and then commercially available dithiol linkers were used for macrocyclization. The highly convergent, site-independent, and modular nature of these two strategies coupled with the unique chemoselectivity of a SNAr transformation allows for the rapid diversity-oriented synthesis of hybrid macrocyclic peptide libraries with varied chemical and structural complexities.
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Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.