The DOI matches its Crossref record; 4 of the 4 references it cites were found in a registry or an index.
Copper-Free Sonogashira Cross-Coupling for Functionalization of Alkyne-Encoded Proteins in Aqueous Medium and in Bacterial Cells
Open accessAbstract
Bioorthogonal reactions suitable for functionalization of genetically or metabolically encoded alkynes, for example, copper-catalyzed azide-alkyne cycloaddition reaction ("click chemistry"), have provided chemical tools to study biomolecular dynamics and function in living systems. Despite its prominence in organic synthesis, copper-free Sonogashira cross-coupling reaction suitable for biological applications has not been reported. In this work, we report the discovery of a robust aminopyrimidine-palladium(II) complex for copper-free Sonogashira cross-coupling that enables selective functionalization of a homopropargylglycine (HPG)-encoded ubiquitin protein in aqueous medium. A wide range of aromatic groups including fluorophores and fluorinated aromatic compounds can be readily introduced into the HPG-containing ubiquitin under mild conditions with good to excellent yields. The suitability of this reaction for functionalization of HPG-encoded ubiquitin in Escherichia coli was also demonstrated. The high efficiency of this new catalytic system should greatly enhance the utility of Sonogashira cross-coupling in bioorthogonal chemistry.
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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
Metalloproteins and metal sensing
Waldron, K. J., Rutherford, J. C., Ford, D., & Robinson, N. J. (2009) · Nature · doi:10.1038/nature08300 · Cited by 1,269
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Cited by
Sapsford, K. E., Algar, W. R., Berti, L., Gemmill, K. B., Casey, B. J., Oh, E., Stewart, M. H., & Medintz, I. L. (2013) · Chemical Reviews · doi:10.1021/cr300143v · Cited by 1,423
Herzberger, J., Niederer, K., Pohlit, H., Seiwert, J., Worm, M., Wurm, F. R., & Frey, H. (2016) · Chemical Reviews · doi:10.1021/acs.chemrev.5b00441 · Cited by 865
Artificial Metalloenzymes: Reaction Scope and Optimization Strategies
Schwizer, F., Okamoto, Y., Heinisch, T., Gu, Y., Pellizzoni, M. M., Lebrun, V., Reuter, R., Köhler, V., Lewis, J. C., & Ward, T. R. (2018) · Chemical Reviews · doi:10.1021/acs.chemrev.7b00014 · Cited by 831
Click Chemistry in Complex Mixtures: Bioorthogonal Bioconjugation
McKay, C. S., & Finn, M. G. (2014) · Chemistry & Biology · doi:10.1016/j.chembiol.2014.09.002 · Cited by 768
Scinto, S. L., Bilodeau, D. A., Hincapie, R., Lee, W., Nguyen, S. S., Xu, M., am Ende, C. W., Finn, M. G., Lang, K., Lin, Q., et al. (2021) · Nature Reviews Methods Primers · doi:10.1038/s43586-021-00028-z · Cited by 592
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Metadata
- Authors
- Li, N., Lim, R. K. V., Edwardraja, S., & Lin, Q.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2011-09-13
- Volume
- 133
- Issue
- 39
- Pages
- 15316-15319
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2051171377
- Cited by
- 266
- References
- 4
- FWCI
- 9.73
- Type
- journal article
- Language
- en
- Open access
- green
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- Li, N., Lim, R. K. V., Edwardraja, S., & Lin, Q. (2011). Copper-Free Sonogashira Cross-Coupling for Functionalization of Alkyne-Encoded Proteins in Aqueous Medium and in Bacterial Cells. Journal of the American Chemical Society. https://doi.org/10.1021/ja2066913
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