Introducing SuFNucs: Sulfamoyl-Fluoride-Functionalized Nucleosides That Undergo Sulfur Fluoride Exchange Reaction
2022
Chrominski, Mikołaj | Ziemkiewicz, Kamil | Kowalska, Joanna | Jemielity, Jacek
The reaction between ribonucleosides and ex situ generated sulfonyl fluoride has been developed. The reaction takes place at the −NH₂ groups of nucleobases, and the resulting nucleosides are equipped with a sulfamoyl fluoride moiety, dubbed SuFNucs. These species undergo a selective sulfur fluoride exchange (SuFEx) reaction with various amines, leading to sulfamide-functionalized derivatives of adenosine, guanosine, and cytidine (SulfamNucs). The scope and examples of further SuFNucs fuctionalization leading to nucleotides, oligonucleotides, and peptide–nucleoside conjugates are presented.
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