ArticleAngewandte Chemie (International ed. in English)2016
Vinylboronic Acids as Fast Reacting, Synthetically Accessible, and Stable Bioorthogonal Reactants in the Carboni-Lindsey Reaction.
Article in Angewandte Chemie (International ed. in English), 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 21 papers.
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Who cites it
21 citing papers in PubMed.
- Biocompatible Chemistry: A Plug-and-Play Toolbox for Chemical Biology Research.Chembiochem : a European journal of chemical biology · 2025Review
- Mutually Orthogonal Bioorthogonal Reactions: Selective Chemistries for Labeling Multiple Biomolecules Simultaneously.Topics in current chemistry (Cham) · 2024Review
- Peptide Boronic Acids by Late-Stage Hydroboration on the Solid Phase.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2024Article
- Recent Advances in Bioorthogonal Ligation and Bioconjugation.Topics in current chemistry (Cham) · 2023Review
- A Chemoselective Polarity-Mismatched Photocatalytic C(spAngewandte Chemie (International ed. in English) · 2023Article
- Arylethynyltrifluoroborate Dienophiles for on Demand Activation of IEDDA Reactions.Bioconjugate chemistry · 2021Article
- Activation and Delivery of Tetrazine-Responsive Bioorthogonal Prodrugs.Molecules (Basel, Switzerland) · 2020Review
- Bioorthogonal Ligations and Cleavages in Chemical Biology.ChemistryOpen · 2020Review
- Developing bioorthogonal probes to span a spectrum of reactivities.Nature reviews. Chemistry · 2020Article
- Fitness Factors for Bioorthogonal Chemical Probes.ACS chemical biology · 2019Article
- Studies on the Stability and Stabilization ofTetrahedron · 2019Article
- Click Chemistry as a Tool for Cell Engineering and Drug Delivery.Molecules (Basel, Switzerland) · 2019Review
- Factors Controlling the Diels-Alder Reactivity of Hetero-1,3-Butadienes.ChemistryOpen · 2018Article
- Highly Stable and Selective Tetrazines for the Coordination-Assisted Bioorthogonal Ligation with Vinylboronic Acids.Bioconjugate chemistry · 2018Article
- Enrichment-triggered prodrug activation demonstrated through mitochondria-targeted delivery of doxorubicin and carbon monoxide.Nature chemistry · 2018Article
- Constructing New Bioorthogonal Reagents and Reactions.Accounts of chemical research · 2018Article
- Modular, Bioorthogonal Strategy for the Controlled Loading of Cargo into a Protein Nanocage.Bioconjugate chemistry · 2018Article
- Vinylboronic Acids as Efficient Bioorthogonal Reactants for Tetrazine Labeling in Living Cells.Bioconjugate chemistry · 2018Article
- Bio-orthogonal Fluorescent Labelling of Biopolymers through Inverse-Electron-Demand Diels-Alder Reactions.Chembiochem : a European journal of chemical biology · 2017Review
- Site-Specific and Stoichiometric Stealth Polymer Conjugates of Therapeutic Peptides and Proteins.Bioconjugate chemistry · 2017Review
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Authors and funding
3 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Bioorthogonal reactions are widely used for the chemical modification of biomolecules. The application of vinylboronic acids (VBAs) as non-strained, synthetically accessible and water-soluble reaction partners in a bioorthogonal inverse electron-demand Diels-Alder (iEDDA) reaction with 3,6-dipyridyl-s-tetrazines is described. Depending on the substituents, VBA derivatives give second-order rate constants up to 27 m(-1) s(-1) in aqueous environments at room temperature, which is suitable for biological labeling applications. The VBAs are shown to be biocompatible, non-toxic, and highly stable in aqueous media and cell lysate. Furthermore, VBAs can be used orthogonally to the strain-promoted alkyne-azide cycloaddition for protein modification, making them attractive complements to the bioorthogonal molecular toolbox.
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