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

Mikołaj Chromiński | Zendy; Kamil Ziemkiewicz | Zendy; Joanna Kowalska | Zendy; Jacek Jemielity | Zendy

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

Author(s) -

Mikołaj Chromiński,

Kamil Ziemkiewicz,

Joanna Kowalska,

Jacek Jemielity

Publication year - 2022

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.2c02034

Subject(s) - chemistry , fluoride , sulfur , combinatorial chemistry , medicinal chemistry , organic chemistry , inorganic chemistry

The reaction between ribonucleosides and ex situ generated sulfonyl fluoride has been developed. The reaction takes place at the -NH 2 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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