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

被引:14
作者
Chrominski, Mikolaj [1 ]
Ziemkiewicz, Kamil [1 ]
Kowalska, Joanna [2 ]
Jemielity, Jacek [1 ]
机构
[1] Univ Warsaw, Ctr New Technol, PL-02097 Warsaw, Poland
[2] Univ Warsaw, Inst Expt Phys, Fac Phys, Div Biophys, PL-02093 Warsaw, Poland
关键词
SUFEX CLICK CHEMISTRY; EX-SITU GENERATION;
D O I
10.1021/acs.orglett.2c02034
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
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.
引用
收藏
页码:4977 / 4981
页数:5
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