Biocompatible SuFEx Click Chemistry: Thionyl Tetrafluoride (SOF₄ )-Derived Connective Hubs for Bioconjugation to DNA and Proteins.

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, incl

SUBMITTER: Liu F 

PROVIDER: S-EPMC6546515 | biostudies-literature | 2019 Jun

REPOSITORIES: biostudies-literature