ArticleACS medicinal chemistry letters2021
2-Cyanoisonicotinamide Conjugation: A Facile Approach to Generate Potent Peptide Inhibitors of the Zika Virus Protease.
Article in ACS medicinal chemistry letters, 2021. 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, 36 citations in OpenAlex.
- Linking Peptides and PNAs: Bioorthogonal Nitrile-Aminothiol Conjugation for Antimicrobial Applications.Methods in molecular biology (Clifton, N.J.) · 2026Article
- Chemical and ribosomal synthesis of atropisomeric and macrocyclic peptides with embedded quinolines.Nature chemistry · 2026Article
- Development of Novel Proline- and Pipecolic Acid-Based Allosteric Inhibitors of Dengue and Zika Virus NS2B/NS3 Protease.Pharmaceuticals (Basel, Switzerland) · 2025Article
- Nitrile-aminothiol bioorthogonal near-infrared fluorogenic probes for ultrasensitive in vivo imaging.Nature communications · 2025Article
- Synthesis of Bicyclic Peptides Using Cyanopyridine-Aminothiol Click Chemistry.Methods in molecular biology (Clifton, N.J.) · 2025Article
- 2-cyanopyridine derivatives enable N-terminal cysteine bioconjugation and peptide bond cleavage of glutathione under aqueous and mild conditions.RSC advances · 2024Article
- Biocompatible strategies for peptide macrocyclisation.Chemical science · 2024Review
- Synthesis and evaluation of phenylimidazole FabK inhibitors as new Anti-C. Difficile agents.Bioorganic & medicinal chemistry · 2023Article
- Boroleucine-Derived Covalent Inhibitors of the ZIKV Protease.ChemMedChem · 2023Article
- Biocompatible and Selective Generation of Bicyclic Peptides.Angewandte Chemie (International ed. in English) · 2022Article
- Genetic Encoding of Cyanopyridylalanine for In-Cell Protein Macrocyclization by the Nitrile-Aminothiol Click Reaction.Angewandte Chemie (International ed. in English) · 2022Article
- An Efficient Approach for the Design and Synthesis of Antimicrobial Peptide-Peptide Nucleic Acid Conjugates.Frontiers in chemistry · 2022Article
- Site-selective generation of lanthanoid binding sites on proteins using 4-fluoro-2,6-dicyanopyridine.Magnetic resonance (Gottingen, Germany) · 2022Article
- Challenges of short substrate analogues as SARS-CoV-2 main protease inhibitors.Bioorganic & medicinal chemistry letters · 2021Article
- Structure and Dynamics of Zika Virus Protease and Its Insights into Inhibitor Design.Biomedicines · 2021Review
Corrections and comments
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Authors and funding
7 authors at 4 institutions in 3 countries.
Funding
No grant is acknowledged in the PubMed record.
Abstract
The rapid generation and modification of macrocyclic peptides in medicinal chemistry is an ever-growing area that can present various synthetic challenges. The reaction between N-terminal cysteine and 2-cyanoisonicotinamide is a new biocompatible click reaction that allows rapid access to macrocyclic peptides. Importantly, 2-cyanoisonicotinamide can be attached to different linkers directly during solid-phase peptide synthesis. The synthesis involves only commercially available precursors, allowing for a fully automated process. We demonstrate the approach for four cyclic peptide ligands of the Zika virus protease NS2B-NS3. Although all peptides display the substrate recognition motif, the activity strongly depends on the linker length, with the shortest cyclization linker corresponding to highest activity (
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Registered trials
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.