ArticleBioconjugate chemistry2018
Highly Stable and Selective Tetrazines for the Coordination-Assisted Bioorthogonal Ligation with Vinylboronic Acids.
Article in Bioconjugate chemistry, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 22 papers.
What it found
Each row is one number read from the abstract, on the scale the paper reported it, with its interval. Left of the dashed line favours the treatment, right favours the comparator. Under each row is the sentence it came from. New to these charts? A ten-minute tutorial.
The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.
The trial behind it
Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.
Neither the registry nor the abstract names a trial number. If this is a trial report, that itself is worth knowing.
Who cites it
22 citing papers in PubMed, 56 citations in OpenAlex.
- Solvatochromism and Click Reactivity of Yellow Tetrazines.Bioconjugate chemistry · 2026Article
- Azo-Povarov Cycloaddition ofThe Journal of organic chemistry · 2026Article
- Beyond Self-Assembly: Bioorthogonal 'Click' Chemistry Strategies for Robust Electrochemical Interfaces in Wearable Biosensors.Biosensors · 2026Review
- Identification of Natural Isonitriles Through Ligation to an Azomethine Imine Probe.Chemistry (Weinheim an der Bergstrasse, Germany) · 2026Article
- Chemical Tagging ofJournal of the American Chemical Society · 2025Article
- Combined Inductive and Dispersion Effects Enhance Bioorthogonal Reactivity of Tetrazines Toward Isonitriles.Angewandte Chemie (International ed. in English) · 2025Article
- Mutually Orthogonal Bioorthogonal Reactions: Selective Chemistries for Labeling Multiple Biomolecules Simultaneously.Topics in current chemistry (Cham) · 2024Review
- Computational Organic Chemistry: The Frontier for Understanding and Designing Bioorthogonal Cycloadditions.Topics in current chemistry (Cham) · 2024Review
- Recent Advances in Bioorthogonal Ligation and Bioconjugation.Topics in current chemistry (Cham) · 2023Review
- Dynamic modulation of matrix adhesiveness induces epithelial-to-mesenchymal transition in prostate cancer cells in 3D.Biomaterials · 2023Article
- Affinity Bioorthogonal Chemistry (ABC) Tags for Site-Selective Conjugation, On-Resin Protein-Protein Coupling, and Purification of Protein Conjugates.Angewandte Chemie (International ed. in English) · 2022Article
- Bioconjugation Strategies for Revealing the Roles of Lipids in Living Cells.Accounts of chemical research · 2022Article
- Intramolecular tetrazine-acryloyl cycloaddition: chemistry and applications.Chemical science · 2022Article
- Development ofPharmaceuticals (Basel, Switzerland) · 2022Article
- Closer Look at Inverse Electron Demand Diels-Alder and Nucleophilic Addition Reactions onTopics in catalysis · 2022Article
- Origin of Increased Reactivity in Rhenium-Mediated Cycloadditions of Tetrazines.The Journal of organic chemistry · 2021Article
- Arylethynyltrifluoroborate Dienophiles for on Demand Activation of IEDDA Reactions.Bioconjugate chemistry · 2021Article
- Activation and Delivery of Tetrazine-Responsive Bioorthogonal Prodrugs.Molecules (Basel, Switzerland) · 2020Review
- Modular Approach to the Functionalization of Polymersomes.Biomacromolecules · 2020Article
- Improving Tumor-to-Background Contrast through Hydrophilic Tetrazines: The Construction ofChemistry (Weinheim an der Bergstrasse, Germany) · 2020Article
Corrections and comments
PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.
Authors and funding
5 authors at 1 institution in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Bioorthogonal reactions are selective transformations that are not affected by any biological functional group and are widely used for chemical modification of biomolecules. Recently, we reported that vinylboronic acids (VBAs) gave exceptionally high reaction rates in the bioorthogonal inverse electron-demand Diels-Alder (iEDDA) reaction with tetrazines bearing a boron-coordinating pyridyl moiety compared to tetrazines lacking such a substituent. In this integrated experimental and theoretical study, we show how the reaction rate of the VBA-tetrazine ligation can be accelerated by shifting the equilibrium from boronic acid to the boronate anion in the reaction mixture. Quantum chemical activation strain analyses reveal that this rate enhancement is a direct consequence of the excellent electron-donating capability of the boronate anion in which the π HOMO is pushed to a higher energy due to the net negative potential of this species. We have explored the second-order rate constants of several tetrazines containing potential VBA-coordinating hydroxyl substituents. We observed an increase in rate constants of several orders of magnitude compared to the tetrazines lacking a hydroxyl substituent. Furthermore, we find the hydroxyl-substituted tetrazines to be more selective toward VBAs than toward the commonly used bioorthogonal reactant norbornene, and more stable in aqueous environment than the previously studied tetrazines containing a pyridyl substituent.
Indexed as
Identifiers
What OpenQuestion holds
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.