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...

Descripción completa

Detalles Bibliográficos
Autores principales: Chrominski, Mikołaj, Ziemkiewicz, Kamil, Kowalska, Joanna, Jemielity, Jacek
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
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
_version_ 1784750002376015872
author Chrominski, Mikołaj
Ziemkiewicz, Kamil
Kowalska, Joanna
Jemielity, Jacek
author_facet Chrominski, Mikołaj
Ziemkiewicz, Kamil
Kowalska, Joanna
Jemielity, Jacek
author_sort Chrominski, Mikołaj
collection PubMed
description [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.
format Online
Article
Text
id pubmed-9295159
institution National Center for Biotechnology Information
language English
publishDate 2022
publisher American Chemical Society
record_format MEDLINE/PubMed
spelling pubmed-92951592022-07-20 Introducing SuFNucs: Sulfamoyl-Fluoride-Functionalized Nucleosides That Undergo Sulfur Fluoride Exchange Reaction Chrominski, Mikołaj Ziemkiewicz, Kamil Kowalska, Joanna Jemielity, Jacek Org Lett [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. American Chemical Society 2022-06-30 2022-07-15 /pmc/articles/PMC9295159/ /pubmed/35771144 http://dx.doi.org/10.1021/acs.orglett.2c02034 Text en © 2022 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Chrominski, Mikołaj
Ziemkiewicz, Kamil
Kowalska, Joanna
Jemielity, Jacek
Introducing SuFNucs: Sulfamoyl-Fluoride-Functionalized Nucleosides That Undergo Sulfur Fluoride Exchange Reaction
title Introducing SuFNucs: Sulfamoyl-Fluoride-Functionalized Nucleosides That Undergo Sulfur Fluoride Exchange Reaction
title_full Introducing SuFNucs: Sulfamoyl-Fluoride-Functionalized Nucleosides That Undergo Sulfur Fluoride Exchange Reaction
title_fullStr Introducing SuFNucs: Sulfamoyl-Fluoride-Functionalized Nucleosides That Undergo Sulfur Fluoride Exchange Reaction
title_full_unstemmed Introducing SuFNucs: Sulfamoyl-Fluoride-Functionalized Nucleosides That Undergo Sulfur Fluoride Exchange Reaction
title_short Introducing SuFNucs: Sulfamoyl-Fluoride-Functionalized Nucleosides That Undergo Sulfur Fluoride Exchange Reaction
title_sort introducing sufnucs: sulfamoyl-fluoride-functionalized nucleosides that undergo sulfur fluoride exchange reaction
url 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
work_keys_str_mv AT chrominskimikołaj introducingsufnucssulfamoylfluoridefunctionalizednucleosidesthatundergosulfurfluorideexchangereaction
AT ziemkiewiczkamil introducingsufnucssulfamoylfluoridefunctionalizednucleosidesthatundergosulfurfluorideexchangereaction
AT kowalskajoanna introducingsufnucssulfamoylfluoridefunctionalizednucleosidesthatundergosulfurfluorideexchangereaction
AT jemielityjacek introducingsufnucssulfamoylfluoridefunctionalizednucleosidesthatundergosulfurfluorideexchangereaction

Ejemplares similares