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Diels–Alder Cycloaddition for Fluorophore Targeting to Specific Proteins inside Living Cells
Open accessAbstract
The inverse-electron-demand Diels-Alder cycloaddition between trans-cyclooctenes and tetrazines is biocompatible and exceptionally fast. We utilized this chemistry for site-specific fluorescence labeling of proteins on the cell surface and inside living mammalian cells by a two-step protocol. Escherichia coli lipoic acid ligase site-specifically ligates a trans-cyclooctene derivative onto a protein of interest in the first step, followed by chemoselective derivatization with a tetrazine-fluorophore conjugate in the second step. On the cell surface, this labeling was fluorogenic and highly sensitive. Inside the cell, we achieved specific labeling of cytoskeletal proteins with green and red fluorophores. By incorporating the Diels-Alder cycloaddition, we have broadened the panel of fluorophores that can be targeted by lipoic acid ligase.
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Cited by
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
Bioorthogonal Reactions for Labeling Proteins
Lang, K., & Chin, J. W. (2014) · ACS Chemical Biology · doi:10.1021/cb4009292 · Cited by 555
Metadata
- Authors
- Liu, D. S., Tangpeerachaikul, A., Selvaraj, R., Taylor, M. T., Fox, J. M., & Ting, A. Y.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2012-01-05
- Volume
- 134
- Issue
- 2
- Pages
- 792-795
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2034337267
- Cited by
- 254
- References
- 0
- FWCI
- 13.32
- Type
- journal article
- Language
- en
- Open access
- green
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- CoChat. (2026). Citation check: Diels–Alder Cycloaddition for Fluorophore Targeting to Specific Proteins inside Living Cells. https://app.cochat.ai/papers/10.1021/ja209325n
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- Liu, D. S., Tangpeerachaikul, A., Selvaraj, R., Taylor, M. T., Fox, J. M., & Ting, A. Y. (2012). Diels–Alder Cycloaddition for Fluorophore Targeting to Specific Proteins inside Living Cells. Journal of the American Chemical Society. https://doi.org/10.1021/ja209325n
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