Covalent protein conjugation facilitates the study of biological processes and the synthesis of therapeutic biomacromolecules. A method that uses vinyl thianthrenium reagents for the site-selective formation of highly reactive episulfonium species on proteins is demonstrated. These in situ-formed intermediates react with diverse nucleophiles, providing access to protein conjugates in one step without purification.
This is a preview of subscription content, log in via an institution to check access.
References
Stephanopoulos, N. & Francis, M. B. Choosing an effective protein bioconjugation strategy. Nat. Chem. Biol. 7, 876–884 (2011). This paper provides advice for selecting the right bioconjugation strategy for a specific purpose.
Ravasco, J. M. J. M., Faustino, H., Trindade, A. & Gois, P. M. P. Bioconjugation with maleimides: a useful tool for chemical biology. Chem. Eur. J. 25, 43–59 (2019). This paper summarizes the development for maleimide reagents as bioconjugation tools.
Bernardes, G. J. L., Chalker, J. M., Errey, J. C. & Davis, B. G. Facile conversion of cysteine and alkyl cysteines to dehydroalanine on protein surfaces: versatile and switchable access to functionalized proteins. J. Am. Chem. Soc. 130, 5052–5053 (2008). This paper reports a method for easy access to dehydroalanine as a versatile chemical linchpin on proteins for bioconjugation.
Juliá, F., Yan, J., Paulus, F. & Ritter, T. Vinyl thianthrenium tetrafluoroborate: a practical and versatile vinylating reagent made from ethylene. J. Am. Chem. Soc. 143, 12992–12998 (2021). This paper introduces vinyl thianthrenium reagents as versatile vinyl electrophiles.
Berger, F. et al. Site-selective and versatile aromatic C−H functionalization by thianthrenation. Nature 567, 223–228 (2019). This paper introduces thianthrenation as a site-selective C–H functionalization method.
Additional information
Publisher’s note Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
This is a summary of: Hartmann, P. et al. Chemoselective umpolung of thiols to episulfoniums for cysteine bioconjugation. Nat. Chem. https://doi.org/10.1038/s41557-023-01388-7 (2023).
Rights and permissions
About this article
Cite this article
Site-selective episulfonium formation on protein surfaces. Nat. Chem. 16, 312–313 (2024). https://doi.org/10.1038/s41557-024-01445-9
Published:
Issue Date:
DOI: https://doi.org/10.1038/s41557-024-01445-9
- Springer Nature Limited