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Rapid, Stable, Chemoselective Labeling of Thiols with Julia–Kocieński‐like Reagents: A Serum‐Stable Alternative to Maleimide‐Based Protein Conjugation
Open accessAbstract
Exquisite chemoselectivity for cysteine has been found for methylsulfonylphenyloxadiazole compounds under various buffer conditions. Furthermore, the resulting protein conjugates have superior stability to cysteine–maleimide conjugates in human plasma (HSA=human serum albumin, MBP-C-HA=maltose-binding protein). This new thiol-click reaction offers a new approach to generate stable protein conjugates and Pegylated proteins.
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Citations
Cites
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
Cited by
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
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
Agarwal, P., & Bertozzi, C. R. (2015) · Bioconjugate Chemistry · doi:10.1021/bc5004982 · Cited by 605
Site-selective protein-modification chemistry for basic biology and drug development
Krall, N., da Cruz, F. P., Boutureira, O., & Bernardes, G. J. L. (2016) · Nature Chemistry · doi:10.1038/nchem.2393 · Cited by 583
Residue-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
Metadata
- Authors
- Toda, N., Asano, S., & Barbas, C. F.
- Venue
- Angewandte Chemie International Edition
- Publisher
- Wiley
- Published
- 2013-10-02
- Volume
- 52
- Issue
- 48
- Pages
- 12592-12596
- ISSN
- 1433-7851 (ISSN-L)
- 1521-3773
- OpenAlex
- W2145493440
- Cited by
- 200
- References
- 1
- FWCI
- 9.04
- Type
- journal article
- Language
- en
- Open access
- green
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- Toda, N., Asano, S., & Barbas, C. F. (2013). Rapid, Stable, Chemoselective Labeling of Thiols with Julia–Kocieński‐like Reagents: A Serum‐Stable Alternative to Maleimide‐Based Protein Conjugation. Angewandte Chemie International Edition. https://doi.org/10.1002/anie.201306241
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