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A Comparative Study of Bioorthogonal Reactions with Azides
Abstract
Detection of metabolites and post-translational modifications can be achieved using the azide as a bioorthogonal chemical reporter. Once introduced into target biomolecules, either metabolically or through chemical modification, the azide can be tagged with probes using one of three highly selective reactions: the Staudinger ligation, the Cu(I)-catalyzed azide-alkyne cycloaddition, or the strain-promoted [3 + 2] cycloaddition. Here, we compared these chemistries in the context of various biological applications, including labeling of biomolecules in complex lysates and on live cell surfaces. The Cu(I)-catalyzed reaction was found to be most efficient for detecting azides in protein samples but was not compatible with live cells due to the toxicity of the reagents. Both the Staudinger ligation and the strain-promoted [3 + 2] cycloaddition using optimized cyclooctynes were effective for tagging azides on live cells. The best reagent for this application was dependent upon the specific structure of the azide. These results provide a guide for biologists in choosing a suitable ligation chemistry.
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Cites
Non-canonical amino acids in protein engineering
Link, A. J., Mock, M. L., & Tirrell, D. A. (2003) · Current Opinion in Biotechnology · doi:10.1016/j.copbio.2003.10.011 · Cited by 393
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
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
Self-citationBioorthogonal Reactions for Labeling Proteins
Lang, K., & Chin, J. W. (2014) · ACS Chemical Biology · doi:10.1021/cb4009292 · Cited by 555
Rapid Oxime and Hydrazone Ligations with Aromatic Aldehydes for Biomolecular Labeling
Dirksen, A., & Dawson, P. E. (2008) · Bioconjugate Chemistry · doi:10.1021/bc800310p · Cited by 373
Laughlin, S. T., & Bertozzi, C. R. (2007) · Nature Protocols · doi:10.1038/nprot.2007.422 · Cited by 337
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Metadata
- Authors
- Agard, N. J., Baskin, J. M., Prescher, J. A., Lo, A., & Bertozzi, C. R.
- Venue
- ACS Chemical Biology
- Publisher
- American Chemical Society (ACS)
- Published
- 2006-10-20
- Volume
- 1
- Issue
- 10
- Pages
- 644-648
- ISSN
- 1554-8929 (ISSN-L)
- 1554-8937
- OpenAlex
- W2009304941
- Cited by
- 744
- References
- 1
- FWCI
- 23.53
- Type
- journal article
- Language
- en
- Open access
- closed
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- Agard, N. J., Baskin, J. M., Prescher, J. A., Lo, A., & Bertozzi, C. R. (2006). A Comparative Study of Bioorthogonal Reactions with Azides. ACS Chemical Biology. https://doi.org/10.1021/cb6003228
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