ArticleJournal of the American Chemical Society2016
Iminoboronate-Based Peptide Cyclization That Responds to pH, Oxidation, and Small Molecule Modulators.
Article in Journal of the American Chemical Society, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 39 papers.
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Who cites it
39 citing papers in PubMed.
- Stepwise-coordinated polymeric nanoplatform enables traceless cytosolic protein delivery and autophagy blockade for enhanced tumor therapy.National science review · 2026Article
- Design of MOFs-based spatially confined catalysis-driven intelligent responsive photoacoustic probe for deep-tissue HMikrochimica acta · 2025Article
- Enhancing WRAP-Based Nanoparticles for Small Interfering Ribonucleic Acid Delivery in pH-Sensitive Environments.ChemMedChem · 2025Article
- Designing Functional and Responsive Molecules with Boronic Acids.Accounts of chemical research · 2025Article
- 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
- Diazaborine-Mediated Bicyclization of Native Peptides with Inducible Reversibility.Organic letters · 2023Article
- Development and Recent Advances in Lysine and N-Terminal Bioconjugation for Peptides and Proteins.Molecules (Basel, Switzerland) · 2023Review
- Integrating a covalent probe with ubiquicidin fragment enables effective bacterial infection imaging.RSC medicinal chemistry · 2022Article
- Lysine-Targeted Reversible Covalent Ligand Discovery for Proteins via Phage Display.Journal of the American Chemical Society · 2022Article
- Lysine-Targeting Reversible Covalent Inhibitors with Long Residence Time.Journal of the American Chemical Society · 2022Article
- Tunable Amine-Reactive Electrophiles for Selective Profiling of Lysine.Angewandte Chemie (International ed. in English) · 2022Article
- Merging the Versatile Functionalities of Boronic Acid with Peptides.International journal of molecular sciences · 2021Review
- 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
- Rapidly Adaptive All-covalent Nanoparticle Surface Engineering.Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Article
- Covalent capture and electrochemical quantification of pathogenicChemical communications (Cambridge, England) · 2021Article
- Strategies to expand peptide functionality through hybridisation with a small molecule component.RSC chemical biology · 2021Review
- Boronic acid based dynamic click chemistry: recent advances and emergent applications.Chemical science · 2020Review
- Peptide Probes of Colistin Resistance Discovered via Chemically Enhanced Phage Display.ACS infectious diseases · 2020Article
- Macrocyclic Modalities Combining Peptide Epitopes and Natural Product Fragments.Journal of the American Chemical Society · 2020Article
Corrections and comments
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Authors and funding
2 authors.
Funding
Abstract
As a rich source of therapeutic agents, peptide natural products usually adopt a cyclic or multicyclic scaffold that minimizes structural flexibility to favor target binding. Inspired by nature, chemists have been interested in developing synthetic cyclic and multicyclic peptides that serve as biological probes and potential therapeutics. Herein we describe a novel strategy for peptide cyclization in which intramolecular iminoboronate formation allows spontaneous cyclization under physiologic conditions to yield monocyclic and bicyclic peptides. Importantly the iminoboronate-based cyclization can be rapidly reversed in response to multiple stimuli, including pH, oxidation, and small molecules. This highly versatile strategy for peptide cyclization should find applications in many areas of chemical biology.
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Registered trials
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