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Selective Labeling of Living Cells by a Photo-Triggered Click Reaction
Open accessAbstract
Phototriggering of the metal-free azide to acetylene cycloaddition reaction was achieved by masking the triple bond of dibenzocyclooctynes as cyclopropenone. Such masked cyclooctynes do not react with azides in the dark. Irradiation of cyclopropenones results in the efficient (Phi(355) = 0.33) and clean regeneration of the corresponding dibenzocyclooctynes, which then undergo facile catalyst-free cycloadditions with azides to give corresponding triazoles under ambient conditions. In situ light activation of a cyclopropenone linked to biotin made it possible to label living cells expressing glycoproteins containing N-azidoacetyl-sialic acid. The cyclopropenone-based phototriggered click chemistry offers exciting opportunities to label living organisms in a temporally and spatially controlled manner and may facilitate the preparation of microarrays.
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Citations
Cited by
Cellular Incorporation of Unnatural Amino Acids and Bioorthogonal Labeling of Proteins
Lang, K., & Chin, J. W. (2014) · Chemical Reviews · doi:10.1021/cr400355w · Cited by 1,035
Photoinduced Electron Transfer Reactions for Macromolecular Syntheses
Dadashi-Silab, S., Doran, S., & Yagci, Y. (2016) · Chemical Reviews · doi:10.1021/acs.chemrev.5b00586 · Cited by 846
Rapid Cu-free click chemistry with readily synthesized biarylazacyclooctynones
Jewett, J. C., Sletten, E. M., & Bertozzi, C. R. (2010) · Journal of the American Chemical Society · doi:10.1021/ja100014q · Cited by 697
Click Chemistry in Materials Science
Xi, W., Scott, T. F., Kloxin, C. J., & Bowman, C. N. (2014) · Advanced Functional Materials · doi:10.1002/adfm.201302847 · Cited by 677
Copper-free click chemistry in living animals
Chang, P. V., Prescher, J. A., Sletten, E. M., Baskin, J. M., Miller, I. A., Agard, N. J., Lo, A., & Bertozzi, C. R. (2010) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.0911116107 · Cited by 655
Metadata
- Authors
- Poloukhtine, A. A., Mbua, N. E., Wolfert, M. A., Boons, G.-J., & Popik, V. V.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2009-10-08
- Volume
- 131
- Issue
- 43
- Pages
- 15769-15776
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W1987334051
- Cited by
- 410
- References
- 0
- FWCI
- 12.93
- Type
- journal article
- Language
- en
- Open access
- green
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- Poloukhtine, A. A., Mbua, N. E., Wolfert, M. A., Boons, G.-J., & Popik, V. V. (2009). Selective Labeling of Living Cells by a Photo-Triggered Click Reaction. Journal of the American Chemical Society. https://doi.org/10.1021/ja9054096
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Contains information from the Semantic Scholar Academic Graph Datasets, made available under the ODC Attribution License (ODC-BY 1.0).
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