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- Title
Biocompatible SuFEx Click Chemistry: Thionyl Tetrafluoride (SOF<sub>4</sub>)‐Derived Connective Hubs for Bioconjugation to DNA and Proteins.
- Authors
Liu, Feng; Wang, Hua; Li, Suhua; Bare, Grant A. L.; Chen, Xuemin; Wang, Chu; Moses, John E.; Wu, Peng; Sharpless, K. Barry
- Abstract
We report here the development of a suite of biocompatible SuFEx transformations from the SOF4‐derived iminosulfur oxydifluoride hub in aqueous buffer conditions. These biocompatible SuFEx reactions of iminosulfur oxydifluorides (R‐N=SOF2) 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=SOF2) 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 SOF4‐derived SuFEx click chemistry in biological applications.
- Subjects
FLUORIDES; CLICK chemistry; BIOCOMPATIBILITY; BIOCONJUGATES; CHEMICAL amplification
- Publication
Angewandte Chemie, 2019, Vol 131, Issue 24, p8113
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201902489