Biocompatible SuFEx Click Chemistry: Thionyl Tetrafluoride (SOF(4) )-Derived Connective Hubs for Bioconjugation to DNA and Proteins

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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