Synthesis of nucleoside oligophosphates by electrophilic activation of phosphorothioate,Organic & Biomolecular Chemistry

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Synthesis of nucleoside oligophosphates by electrophilic activation of phosphorothioate
Organic & Biomolecular Chemistry ( IF 2.9 ) Pub Date : 2023-04-26 , DOI: 10.1039/d2ob02260e
Shogo Hasegawa ₁ , Masahito Inagaki ₁ , Shunichi Kato ₁ , Zhenmin Li ₁ , Yasuaki Kimura ₁ , Hiroshi Abe _{1,

2,

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Affiliation

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.

中文翻译：

硫代磷酸酯亲电活化合成低聚核苷

我们在此报告了一种基于 5'-硫代磷酸酯核苷酸亲电激活的核苷寡磷酸酯的新合成方法。用 2,4-二硝基氯苯 (DNCB) 处理硫代磷酸酯有效地提供了关键的活化物质，亲电子硫酯核苷酸 (EPT-Ns)，它与各种磷酸盐试剂偶联以提供目标核苷低聚磷酸盐，包括 mRNA 帽类似物。

更新日期：2023-04-27

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