ArticleOrganic & biomolecular chemistry2017
Computationally guided discovery of a reactive, hydrophilic trans-5-oxocene dienophile for bioorthogonal labeling.
Article in Organic & biomolecular chemistry, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. An erratum has been issued. Cited by 27 papers.
What it found
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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
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Who cites it
27 citing papers in PubMed, 49 citations in OpenAlex.
- Tetrazine Ligation in Living Systems: Beyond Fast Kinetics to Effective Bioorthogonality.Chemistry (Weinheim an der Bergstrasse, Germany) · 2026Review
- Attachment of 2-Pyridyltetrazine Affinity Bioorthogonal Chemistry (ABC) Tags to Proteins for Site-Selective Bioorthogonal Chemistry.Methods in molecular biology (Clifton, N.J.) · 2026Article
- Article
- Imaging Interorganelle Phospholipid Transport by Extended Synaptotagmins Using Bioorthogonally Tagged Lipids.ACS chemical biology · 2024Article
- Trans-cyclooctene-a Swiss army knife for bioorthogonal chemistry: exploring the synthesis, reactivity, and applications in biomedical breakthroughs.EJNMMI radiopharmacy and chemistry · 2024Review
- Imaging Phospholipase D Activity with Clickable Alcohols via Transphosphatidylation.Methods in molecular biology (Clifton, N.J.) · 2024Article
- Bioorthogonal Chemistry in Cellular Organelles.Topics in current chemistry (Cham) · 2023Review
- Development ofChemical communications (Cambridge, England) · 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
- Imaging and Editing the Phospholipidome.Accounts of chemical research · 2022Review
- Catalytic Activation of Bioorthogonal Chemistry with Light (CABL) Enables Rapid, Spatiotemporally Controlled Labeling and No-Wash, Subcellular 3D-Patterning in Live Cells Using Long Wavelength Light.Journal of the American Chemical Society · 2022Article
- Activity-based, bioorthogonal imaging of phospholipase D reveals spatiotemporal dynamics of GPCR-Gq signaling.Cell chemical biology · 2022Article
- General, Divergent Platform for Diastereoselective Synthesis of trans-Cyclooctenes with High Reactivity and Favorable Physiochemical Properties*.Angewandte Chemie (International ed. in English) · 2021Article
- Predicting reactivity for bioorthogonal cycloadditions involving nitrones.RSC advances · 2020Article
- Improving Tumor-to-Background Contrast through Hydrophilic Tetrazines: The Construction ofChemistry (Weinheim an der Bergstrasse, Germany) · 2020Article
- Preclinical Evaluation of a NovelACS omega · 2020Article
- Spatiotemporal control of phosphatidic acid signaling with optogenetic, engineered phospholipase Ds.The Journal of cell biology · 2020Article
- IMPACT: Imaging phospholipase d activity with clickable alcohols via transphosphatidylation.Methods in enzymology · 2020Article
- Developing bioorthogonal probes to span a spectrum of reactivities.Nature reviews. Chemistry · 2020Article
- Fitness Factors for Bioorthogonal Chemical Probes.ACS chemical biology · 2019Article
Corrections and comments
- Erratum issued
Authors and funding
9 authors at 3 institutions in 2 countries.
Funding
Abstract
The use of organic chemistry principles and prediction techniques has enabled the development of new bioorthogonal reactions. As this "toolbox" expands to include new reaction manifolds and orthogonal reaction pairings, the continued development of existing reactions remains an important objective. This is particularly important in cellular imaging, where non-specific background fluorescence has been linked to the hydrophobicity of the bioorthogonal moiety. Here we report that trans-5-oxocene (oxoTCO) displays enhanced reactivity and hydrophilicity compared to trans-cyclooctene (TCO) in the tetrazine ligation reaction. Aided by ab initio calculations we show that the insertion of a single oxygen atom into the trans-cyclooctene (TCO) ring system is sufficient to impart aqueous solubility and also results in significant rate acceleration by increasing angle strain. We demonstrate the rapid and quantitative cycloaddition of oxoTCO using a water-soluble tetrazine derivative and a protein substrate containing a site-specific genetically encoded tetrazine moiety both in vitro and in vivo. We anticipate that oxoTCO will find use in studies where hydrophilicity and fast bioconjugation kinetics are paramount.
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.