Issue 19, 2023

Synthesis of nucleoside oligophosphates by electrophilic activation of phosphorothioate

Abstract

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.

Graphical abstract: Synthesis of nucleoside oligophosphates by electrophilic activation of phosphorothioate

Supplementary files

Article information

Article type
Communication
Submitted
14 Dec 2022
Accepted
03 Apr 2023
First published
26 Apr 2023

Org. Biomol. Chem., 2023,21, 3997-4001

Author version available

Synthesis of nucleoside oligophosphates by electrophilic activation of phosphorothioate

S. Hasegawa, M. Inagaki, S. Kato, Z. Li, Y. Kimura and H. Abe, Org. Biomol. Chem., 2023, 21, 3997 DOI: 10.1039/D2OB02260E

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