title: Iminoboronate-Based Peptide Cyclization That Responds to pH, Oxidation, and Small Molecule Modulators.
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.
authors: Department of Chemistry, Merkert Chemistry Center, Boston College , 2609 Beacon Street, Chestnut Hill, Massachusetts 02467, United States.
authors: Anupam
authors: A
authors: Bandyopadhyay
authors: Department of Chemistry, Merkert Chemistry Center, Boston College , 2609 Beacon Street, Chestnut Hill, Massachusetts 02467, United States.
authors: Jianmin
authors: J
authors: Gao
mesh_terms: D001897:Boronic Acids / Q000737:chemistry*; D003500:Cyclization / Q000187:drug effects; D006863:Hydrogen-Ion Concentration; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010456:Peptides, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry; D054852:Small Molecule Libraries / Q000737:chemistry* / Q000494:pharmacology; D013816:Thermodynamics
chemical_list: D001897:Boronic Acids; D010456:Peptides, Cyclic; D054852:Small Molecule Libraries