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Introducing SuFNucs: Sulfamoyl-Fluoride-Functionalized Nucleosides That Undergo Sulfur Fluoride Exchange Reaction
[Image: see text] 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 select...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American Chemical Society
2022
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9295159/ https://www.ncbi.nlm.nih.gov/pubmed/35771144 http://dx.doi.org/10.1021/acs.orglett.2c02034 |
Sumario: | [Image: see text] 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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