The Bioorthogonal Isonitrile–Chlorooxime Ligation

2019/11/11 by Rebecca J. B. Schäfer, Mattia Riccardo Monaco, Mattia R. Monaco +5 · 24 citations
Chemistry · Biochemistry, Genetics and Molecular Biology · Medicine · #Click Chemistry and Applications #Chemical Synthesis and Analysis #Monoclonal and Polyclonal Antibodies Research

paper · doi:10.1021/jacs.9b07632

Abstract

Bioorthogonal reactions are valuable tools for the selective labeling and imaging of natural products and proteins. Here, we present the reaction between isonitriles and chlorooximes as a ligation that proceeds quickly (k ≈ 1 M–1 s–1) and with high chemoselectivity in an aqueous environment. Imaging of metabolically labeled cell surface glycans underlined the tolerance of the ligation to common functional groups in cellular systems. Live-cell dual-labeling experiments revealed that the isonitrile–chlorooxime ligation is orthogonal to the strain-promoted azide–alkyne cycloaddition.

Citations

• A Strain-Promoted [3 + 2] Azide−Alkyne Cycloaddition for Covalent Modification of Biomolecules in Living Systems
• Bioconjugation by Copper(I)-Catalyzed Azide-Alkyne [3 + 2] Cycloaddition
• Tetrazine Ligation: Fast Bioconjugation Based on Inverse-Electron-Demand Diels−Alder Reactivity
• Bioorthogonal Removal of 3-Isocyanopropyl Groups Enables the Controlled Release of Fluorophores and Drugs in Vivo

Cited by

• Isonitriles: Versatile Handles for the Bioorthogonal Functionalization of Proteins. [europepmc]
• Triple, Mutually Orthogonal Bioorthogonal Pairs through the Design of Electronically Activated Sulfamate-Containing Cycloalkynes. [europepmc]
• Isocyanides: Promising Functionalities in Bioorthogonal Labeling of Biomolecules. [europepmc]
• Developing bioorthogonal probes to span a spectrum of reactivities. [europepmc]
• Supramolecular Host-Guest Hydrogels for Corneal Regeneration. [europepmc]
• Bacteria-Assisted Transport of Nanomaterials to Improve Drug Delivery in Cancer Therapy. [europepmc]
• Fast and Cysteine-Specific Modification of Peptides, Proteins and Bacteriophage Using Chlorooximes. [europepmc]
• Biosynthesis of Isonitrile- and Alkyne-Containing Natural Products. [europepmc]
• Facile synthesis of O -acylhydroxamates via reaction of oxime chlorides with carboxylic acids. [europepmc]
• Facile Synthesis of Tricyclic 1,2,4-Oxadiazolines-Fused Tetrahydro-Isoquinolines from Oxime Chlorides with 3,4-Dihydroisoquinoline Imines. [europepmc]
• Catch-enrich-release approach for amine-containing natural products. [europepmc]
• Identification of Isonitrile-Containing Natural Products in Complex Biological Matrices through Ligation with Chlorooximes. [europepmc]
• Site-specific dual encoding and labeling of proteins via genetic code expansion. [europepmc]
• A Cysteine-Directed Proximity-Driven Crosslinking Method for Native Peptide Bicyclization. [europepmc]
• 4-Isocyanoindole-2'-deoxyribonucleoside (4ICIN): An Isomorphic Indole Nucleoside Suitable for Inverse Electron Demand Diels-Alder Reactions. [europepmc]
• Rational Design of Palladium(II) Indenyl and Allyl Complexes Bearing Phosphine and Isocyanide Ancillary Ligands with Promising Antitumor Activity. [europepmc]
• Biosynthesis of isonitrile lipopeptides. [europepmc]
• Mutually Orthogonal Bioorthogonal Reactions: Selective Chemistries for Labeling Multiple Biomolecules Simultaneously. [europepmc]
• Isonitrile biosynthesis by non-heme iron(II)-dependent oxidases/decarboxylases. [europepmc]
• The Evolution of Fluorescein into A Potential Theranostic Tool. [europepmc]
• Bioorthogonal Engineering of Cellular Microenvironments Using Isonitrile Ligations. [europepmc]
• Discovery of Isonitrile Lipopeptide Chalkophores from Pathogenic Mycobacteria. [europepmc]
• Identification of Natural Isonitriles Through Ligation to an Azomethine Imine Probe. [europepmc]
• Creating unimolecular multivalent diversity in protein conjugates via the Passerini multicomponent bioconjugation with isocyanoproteins. [europepmc]

Related

• Photoinducible Bioorthogonal Chemistry: A Spatiotemporally Controllable Tool to Visualize and Perturb Proteins in Live Cells
• Bioconjugation with Strained Alkenes and Alkynes
• Bioorthogonal Removal of 3-Isocyanopropyl Groups Enables the Controlled Release of Fluorophores and Drugs in Vivo
• Selective Labeling of Living Cells by a Photo-Triggered Click Reaction
• A Strain-Promoted [3 + 2] Azide−Alkyne Cycloaddition for Covalent Modification of Biomolecules in Living Systems