Synthesis of nucleoside oligophosphates by electrophilic activation of phosphorothioate.

Nucleosides Nucleotides Phosphates RNA, Messenger

Journal

Organic & biomolecular chemistry
ISSN: 1477-0539
Titre abrégé: Org Biomol Chem
Pays: England
ID NLM: 101154995

Informations de publication

Date de publication:
17 05 2023
Historique:
medline: 19 5 2023
pubmed: 15 5 2023
entrez: 15 5 2023
Statut: epublish

Résumé

We herein report a new synthetic method for nucleoside oligophosphates based on electrophilic activation of 5'-phosphorothioate nucleotides. The treatment of phosphorothioate with 2,4-dinitrochlorobenzene (DNCB) efficiently afforded the key activated species, electrophilic thioester nucleotides (EPT-Ns), which were coupled with various phosphate reagents to afford the target nucleoside oligophosphates, including an mRNA cap analog.

Identifiants

DOI: 10.1039/d2ob02260e PMID: 37186249
pubmed: 37186249
doi: 10.1039/d2ob02260e
doi:

Substances chimiques

Nucleosides 0
Nucleotides 0
thiophosphoric acid TYM4M7EWCW
Phosphates 0
RNA, Messenger 0

Types de publication

Journal Article Research Support, Non-U.S. Gov't

Langues

eng

Sous-ensembles de citation

IM

Pagination

3997-4001

Auteurs

Shogo Hasegawa (S)

Graduate School of Science, Nagoya University, Japan. h-abe@chem.nagoya-u.ac.jp.

Masahito Inagaki (M)

Graduate School of Science, Nagoya University, Japan. h-abe@chem.nagoya-u.ac.jp.
ORCID: 0000-0001-9556-4586

Shunichi Kato (S)

Graduate School of Science, Nagoya University, Japan. h-abe@chem.nagoya-u.ac.jp.

Zhenmin Li (Z)

Graduate School of Science, Nagoya University, Japan. h-abe@chem.nagoya-u.ac.jp.

Yasuaki Kimura (Y)

Graduate School of Science, Nagoya University, Japan. h-abe@chem.nagoya-u.ac.jp.
ORCID: 0000-0002-3609-602X

Hiroshi Abe (H)

Graduate School of Science, Nagoya University, Japan. h-abe@chem.nagoya-u.ac.jp.
CREST, Japan Science and Technology Agency, Japan.
Institute for Glyco-core Research (iGCORE), Japan.
ORCID: 0000-0003-0048-3789

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Classifications MeSH

questionsmedicales.fr › Acides nucléiques, nucléotides et nucléosides › Nucléosides › Synthesis of nucleoside oligophosphates by...
questionsmedicales.fr › Acides nucléiques, nucléotides et nucléosides › Nucléotides › Synthesis of nucleoside oligophosphates by...
questionsmedicales.fr › Produits chimiques inorganiques › Composés du phosphore › Acides du phosphore › Acides phosphoriques › Phosphates › Synthesis of nucleoside oligophosphates by...
questionsmedicales.fr › Acides nucléiques, nucléotides et nucléosides › Acides nucléiques › ARN › ARN messager › Synthesis of nucleoside oligophosphates by...