ArticleAngewandte Chemie (International ed. in English)2020
Divergent Synthesis of Monosubstituted and Unsymmetrical 3,6-Disubstituted Tetrazines from Carboxylic Ester Precursors.
Article in Angewandte Chemie (International ed. in English), 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 27 papers.
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Who cites it
27 citing papers in PubMed, 52 citations in OpenAlex.
- Tetrazine Ligation in Living Systems: Beyond Fast Kinetics to Effective Bioorthogonality.Chemistry (Weinheim an der Bergstrasse, Germany) · 2026Review
- Azo-Povarov Cycloaddition ofThe Journal of organic chemistry · 2026Article
- Scalable Flow Synthesis of Genetically Encodable Tetrazine Amino Acids.Organic process research & development · 2026Article
- Second-Generation Catalyst System for Ag-Mediated Liebeskind-Srogl Coupling of Tetrazine Thioethers with Arylboronic Acids.The Journal of organic chemistry · 2025Article
- Multi-postpolymerization Functionalization of PLA Enabled by Sulfide Tetrazines as a Single End-Group Moiety.ACS polymers Au · 2025Article
- Tuning Encodable Tetrazine Chemistry for Site-Specific Protein Bioorthogonal Ligations.Angewandte Chemie (International ed. in English) · 2025Article
- Quantitative Protein Labeling in Live Cells by Controlling the Redox State of Encoded Tetrazines.Journal of the American Chemical Society · 2025Article
- Investigation of Proteome-Tetrazine Reactivity for a Highly Selective Tetrazine Ligation in Live Cells.ACS central science · 2025Article
- Sulfur-tetrazine as highly efficient visible-light activatable photo-trigger for designing photoactivatable fluorescence biomolecules.Journal of materials chemistry. B · 2024Article
- Synthesis of CThe Journal of organic chemistry · 2024Article
- Recent Progress in Synthetic Applications of Hypervalent Iodine(III) Reagents.Chemical reviews · 2024Review
- Enabling Universal Access to Rapid and Stable Tetrazine Bioorthogonal Probes through Triazolyl-Tetrazine Formation.JACS Au · 2024Article
- Fluorescence-Based Enzyme Activity Assay: Ascertaining the Activity and Inhibition of Endocannabinoid Hydrolytic Enzymes.International journal of molecular sciences · 2024Review
- Advances in the Synthesis of Bioorthogonal Reagents: s-Tetrazines, 1,2,4-Triazines, Cyclooctynes, Heterocycloheptynes, and trans-Cyclooctenes.Topics in current chemistry (Cham) · 2024Review
- Minimalist TetrazineJournal of the American Chemical Society · 2024Article
- Article
- Thiomethyltetrazines Are Reversible Covalent Cysteine Warheads Whose Dynamic Behavior can be "Switched Off"Journal of the American Chemical Society · 2023Article
- Green Synthesis of Aromatic Nitrogen-Containing Heterocycles by Catalytic and Non-Traditional Activation Methods.Molecules (Basel, Switzerland) · 2023Review
- Solid-Phase Synthesis ofOrganic letters · 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
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Authors and funding
6 authors at 2 institutions in 1 country.
Funding
Abstract
Since tetrazines are important tools to the field of bioorthogonal chemistry, there is a need for new approaches to synthesize unsymmetrical and 3-monosubstituted tetrazines. Described here is a general, one-pot method for converting (3-methyloxetan-3-yl)methyl carboxylic esters into 3-thiomethyltetrazines. These versatile intermediates were applied to the synthesis of unsymmetrical tetrazines through Pd-catalyzed cross-coupling and in the first catalytic thioether reduction to access monosubstituted tetrazines. This method enables the development of new tetrazine compounds possessing a favorable combination of kinetics, small size, and hydrophilicity. It was applied to a broad range of aliphatic and aromatic ester precursors and to the synthesis of heterocycles including BODIPY fluorophores and biotin. In addition, a series of tetrazine probes for monoacylglycerol lipase (MAGL) were synthesized and the most reactive one was applied to the labeling of endogenous MAGL in live cells.
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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.