Liu, F., Wang, H., Li, S., Bare, G. A. L., Chen, X., Wang, C., Moses, J. E., Wu, P., Sharpless, K. B. (June 2019) Biocompatible SuFEx Click Chemistry: Thionyl Tetrafluoride (SOF(4) )-Derived Connective Hubs for Bioconjugation to DNA and Proteins. Angew Chem Int Ed Engl, 58 (24). pp. 8029-8033. ISSN 1433-7851 (Print)1433-7851
Abstract
We report here the development of a suite of biocompatible SuFEx transformations from the SOF(4) -derived iminosulfur oxydifluoride hub in aqueous buffer conditions. These biocompatible SuFEx reactions of iminosulfur oxydifluorides (R-N=SOF(2) ) with primary amines give sulfamides (8 examples, up to 98�%), while the reaction with secondary amines furnish sulfuramidimidoyl fluoride products (8 examples, up to 97�%). Likewise, under mild buffered conditions, phenols react with the iminosulfur oxydifluorides (Ar-N=SOF(2) ) to produce sulfurofluoridoimidates (13 examples, up to 99�%), which can themselves be further modified by nucleophiles. These transformations open the potential for asymmetric and trisubstituted linkages projecting from the sulfur(VI) center, including versatile S-N and S-O connectivity (9 examples, up to 94�%). Finally, the SuFEx bioconjugation of iminosulfur oxydifluorides to amine-tagged single-stranded DNA and to BSA protein demonstrate the potential of SOF(4) -derived SuFEx click chemistry in biological applications.
| Item Type: | Paper |
|---|---|
| Additional Information: | Angewandte Chemie (International ed. in English) |
| Uncontrolled Keywords: | *DNA encoded libraries *SuFEx *bioconjugation *click chemistry *protein modification |
| Subjects: | chemistry chemistry > techniques > click chemistry chemistry > techniques |
| CSHL Authors: | |
| Communities: | CSHL labs > Moses lab |
| Depositing User: | Matthew Dunn |
| Date: | 11 June 2019 |
| Date Deposited: | 08 Jan 2021 17:15 |
| Last Modified: | 02 Feb 2024 17:05 |
| PMCID: | PMC6546515 |
| Related URLs: | |
| URI: | https://repository.cshl.edu/id/eprint/39585 |
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