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Facile Conversion of Cysteine and Alkyl Cysteines to Dehydroalanine on Protein Surfaces: Versatile and Switchable Access to Functionalized Proteins
Abstract
An efficient and robust oxidative elimination of cysteine to dehydroalanine has been discovered. The reaction is induced by O-mesitylenesulfonylhydroxylamine (MSH) and is compatible with methionine. The key elimination has been executed on protein surfaces and allows ready access to different post-translationally modified proteins through conjugate addition of sulfur nucleophiles to dehydroalanine. Treatment of the resulting thioether with MSH results in regeneration of dehydroalanine, allowing a "functional switch" by subsequent addition of a different thiol.
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Citations
Cited by
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Sletten, E. M., & Bertozzi, C. R. (2009) · Angewandte Chemie International Edition · doi:10.1002/anie.200900942 · Cited by 3,165
Adding New Chemistries to the Genetic Code
Liu, C. C., & Schultz, P. G. (2010) · Annual Review of Biochemistry · doi:10.1146/annurev.biochem.052308.105824 · Cited by 1,725
Chemical Modification of Proteins at Cysteine: Opportunities in Chemistry and Biology
Chalker, J. M., Bernardes, G. J. L., Lin, Y. A., & Davis, B. G. (2009) · Chemistry – An Asian Journal · doi:10.1002/asia.200800427 · Cited by 649
Self-citationResidue-Specific Peptide Modification: A Chemist’s Guide
deGruyter, J. N., Malins, L. R., & Baran, P. S. (2017) · Biochemistry · doi:10.1021/acs.biochem.7b00536 · Cited by 573
Algar, W. R., Prasuhn, D. E., Stewart, M. H., Jennings, T. L., Blanco-Canosa, J. B., Dawson, P. E., & Medintz, I. L. (2011) · Bioconjugate Chemistry · doi:10.1021/bc200065z · Cited by 502
Metadata
- Authors
- Bernardes, G. J. L., Chalker, J. M., Errey, J. C., & Davis, B. G.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2008-03-22
- Volume
- 130
- Issue
- 15
- Pages
- 5052-5053
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2166771133
- Cited by
- 354
- References
- 0
- FWCI
- 12.05
- Type
- journal article
- Language
- en
- Open access
- closed
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- Bernardes, G. J. L., Chalker, J. M., Errey, J. C., & Davis, B. G. (2008). Facile Conversion of Cysteine and Alkyl Cysteines to Dehydroalanine on Protein Surfaces: Versatile and Switchable Access to Functionalized Proteins. Journal of the American Chemical Society. https://doi.org/10.1021/ja800800p
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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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