ArticleJournal of the American Chemical Society2018
Readily Accessible Ambiphilic Cyclopentadienes for Bioorthogonal Labeling.
Article in Journal of the American Chemical Society, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 13 papers.
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Who cites it
13 citing papers in PubMed.
- Combined Inductive and Dispersion Effects Enhance Bioorthogonal Reactivity of Tetrazines Toward Isonitriles.Angewandte Chemie (International ed. in English) · 2025Article
- Computational Organic Chemistry: The Frontier for Understanding and Designing Bioorthogonal Cycloadditions.Topics in current chemistry (Cham) · 2024Review
- On the Question of Zwitterionic Intermediates in the [3+2] Cycloaddition Reactions between Aryl Azides and Ethyl Propiolate.Molecules (Basel, Switzerland) · 2023Article
- Computational study of an oxetane 4Tetrahedron letters · 2023Article
- Orthogonal Inverse-Electron-Demand Cycloaddition Reactions Controlled by Frontier Molecular Orbital Interactions.Organic letters · 2023Article
- Article
- Click Chemistry with Cyclopentadiene.Chemical reviews · 2021Review
- Bioorthogonal Ligations and Cleavages in Chemical Biology.ChemistryOpen · 2020Review
- Differential Effects of Nitrogen Substitution in 5- and 6-Membered Aromatic Motifs.Chemistry (Weinheim an der Bergstrasse, Germany) · 2020Article
- Hyperconjugative Antiaromaticity Activates 4Organic letters · 2019Article
- Structural Distortion of Cycloalkynes Influences Cycloaddition Rates both by Strain and Interaction Energies.Chemistry (Weinheim an der Bergstrasse, Germany) · 2019Article
- Secondary Orbital Interactions Enhance the Reactivity of Alkynes in Diels-Alder Cycloadditions.Journal of the American Chemical Society · 2019Article
- Hyperconjugative Aromaticity and Antiaromaticity Control the Reactivities and π-Facial Stereoselectivities of 5-Substituted Cyclopentadiene Diels-Alder Cycloadditions.The Journal of organic chemistry · 2018Article
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Authors and funding
4 authors.
Funding
Abstract
A new class of bioorthogonal reagents based on the cyclopentadiene scaffold is described. The diene 6,7,8,9-tetrachloro-1,4-dioxospiro[4,4]nona-6,8-diene (a tetrachlorocyclopentadiene ketal, TCK) is ambiphilic and self-orthogonal with remarkable stability. The diene reacts rapidly with a trans-cyclooctene and an endo-bicyclononyne, but slowly with dibenzoazacyclooctyne (DIBAC), allowing for tandem labeling studies with mutually orthogonal azides that react rapidly with DIBAC. TCK analogues are synthesized in three steps from inexpensive, commercially available starting materials.
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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.