Introducing SuFNucs: Sulfamoyl-Fluoride-Functionalized Nucleosides That Undergo Sulfur Fluoride Exchange Reaction

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.

Automated summary

A reaction between ribonucleosides and ex situ generated sulfonyl fluoride has been developed, leading to nucleosides equipped with a sulfamoyl fluoride moiety. These nucleosides undergo a selective sulfur fluoride exchange (SuFEx) reaction with various amines to form sulfamide-functionalized derivatives. The study also demonstrates the scope and examples of further functionalization to nucleotides, oligonucleotides, and peptide-nucleoside conjugates.