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Biocompatible SuFEx Click Chemistry: Thionyl Tetrafluoride (SOF 4 )‐Derived Connective Hubs for Bioconjugation to DNA and Proteins
Author(s) -
Liu Feng,
Wang Hua,
Li Suhua,
Bare Grant A. L.,
Chen Xuemin,
Wang Chu,
Moses John E.,
Wu Peng,
Sharpless K. Barry
Publication year - 2019
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201902489
Subject(s) - bioconjugation , chemistry , biocompatible material , click chemistry , combinatorial chemistry , amine gas treating , nucleophile , organic chemistry , catalysis , medicine , biomedical engineering
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.