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Tetrazine Ligation: Fast Bioconjugation Based on Inverse-Electron-Demand Diels−Alder Reactivity
Open accessAbstract
Described is a bioorthogonal reaction that proceeds with unusually fast reaction rates without need for catalysis: the cycloaddition of s-tetrazine and trans-cyclooctene derivatives. The reactions tolerate a broad range of functionality and proceed in high yield in organic solvents, water, cell media, or cell lysate. The rate of the ligation between trans-cyclooctene and 3,6-di-(2-pyridyl)-s-tetrazine is very rapid (k2 2000 M-1 s-1). This fast reactivity enables protein modification at low concentration.
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Cited by
Bioorthogonal Chemistry: Fishing for Selectivity in a Sea of Functionality
Sletten, E. M., & Bertozzi, C. R. (2009) · Angewandte Chemie International Edition · doi:10.1002/anie.200900942 · Cited by 3,165
Cu-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
Designing degradable hydrogels for orthogonal control of cell microenvironments
Kharkar, P. M., Kiick, K. L., & Kloxin, A. M. (2013) · Chem. Soc. Rev. · doi:10.1039/c3cs60040h · Cited by 717
Tassa, C., Shaw, S. Y., & Weissleder, R. (2011) · Accounts of Chemical Research · doi:10.1021/ar200084x · Cited by 653
Bioorthogonal Reactions for Labeling Proteins
Lang, K., & Chin, J. W. (2014) · ACS Chemical Biology · doi:10.1021/cb4009292 · Cited by 555
Metadata
- Authors
- Blackman, M. L., Royzen, M., & Fox, J. M.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2008-09-18
- Volume
- 130
- Issue
- 41
- Pages
- 13518-13519
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2062524026
- Cited by
- 1,679
- References
- 0
- FWCI
- 18.82
- Type
- journal article
- Language
- en
- Open access
- green
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- CoChat. (2026). Citation check: Tetrazine Ligation: Fast Bioconjugation Based on Inverse-Electron-Demand Diels−Alder Reactivity. https://app.cochat.ai/papers/10.1021/ja8053805
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- Blackman, M. L., Royzen, M., & Fox, J. M. (2008). Tetrazine Ligation: Fast Bioconjugation Based on Inverse-Electron-Demand Diels−Alder Reactivity. Journal of the American Chemical Society. https://doi.org/10.1021/ja8053805
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Semantic Scholar’s data is described in: Kinney, R., et al. (2023). The Semantic Scholar Open Data Platform. arXiv:2301.10140.
