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Second-Generation Difluorinated Cyclooctynes for Copper-Free Click Chemistry
Open accessAbstract
The 1,3-dipolar cycloaddition of azides and activated alkynes has been used for site-selective labeling of biomolecules in vitro and in vivo. While copper catalysis has been widely employed to activate terminal alkynes for [3 + 2] cycloaddition, this method, often termed "click chemistry", is currently incompatible with living systems because of the toxicity of the metal. We recently reported a difluorinated cyclooctyne (DIFO) reagent that rapidly reacts with azides in living cells without the need for copper catalysis. Here we report a novel class of DIFO reagents for copper-free click chemistry that are considerably more synthetically tractable. The new analogues maintained the same elevated rates of [3 + 2] cycloaddition as the parent compound and were used for imaging glycans on live cells. These second-generation DIFO reagents should expand the use of copper-free click chemistry in the hands of biologists.
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Tornøe, C. W., Christensen, C., & Meldal, M. (2002) · The Journal of Organic Chemistry · doi:10.1021/jo011148j · Cited by 8,696
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Self-citationCu-free click cycloaddition reactions in chemical biology
Jewett, J. C., & Bertozzi, C. R. (2010) · Chemical Society Reviews · doi:10.1039/b901970g · Cited by 1,684
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Kharkar, P. M., Kiick, K. L., & Kloxin, A. M. (2013) · Chem. Soc. Rev. · doi:10.1039/c3cs60040h · Cited by 717
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
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Metadata
- Authors
- Codelli, J. A., Baskin, J. M., Agard, N. J., & Bertozzi, C. R.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2008-08-05
- Volume
- 130
- Issue
- 34
- Pages
- 11486-11493
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2037796752
- Cited by
- 552
- References
- 1
- FWCI
- 26.41
- Type
- journal article
- Language
- en
- Open access
- hybrid
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- Codelli, J. A., Baskin, J. M., Agard, N. J., & Bertozzi, C. R. (2008). Second-Generation Difluorinated Cyclooctynes for Copper-Free Click Chemistry. Journal of the American Chemical Society. https://doi.org/10.1021/ja803086r
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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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