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通过三甲基氯硅烷介导的核苷三磷酸与胺的反应合成新型核苷5'-氨基磷酸酯。

Novel synthesis of nucleoside 5'-phosphoramidates through reaction of nucleoside triphosphates with amines mediated by trimethylsilyl chloride.

作者信息

Zhu Jigang, Han Bo, Fu Hua, Jiang Yuyang, Zhao Yufen

机构信息

Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology, Ministry of Education, Department of Chemistry, Tsinghua University, Beijing 100084, P. R. China.

出版信息

J Org Chem. 2005 Aug 19;70(17):6676-9. doi: 10.1021/jo050716i.

Abstract

Reaction of nucleoside triphosphates (NTPs) with amines in pyridine mediated by trimethylsilyl chloride produced nucleoside 5'-phosphoramidates in moderate yields without any preprotection of nucleosides and amino acid methyl esters. The reaction pathway is very similar to the mechanism of the RNA capping reaction, DNA or RNA ligation reaction, and catalysis of hydrolases and nucleases involving the formation of covalent enzyme-NMP (nucleoside 5'-monophosphate) intermediates in biological systems, which could provide a valuable clue for the enzymatic reactions.

摘要

在三甲基氯硅烷介导下,核苷三磷酸(NTPs)与吡啶中的胺反应,无需对核苷和氨基酸甲酯进行任何预先保护,就能以中等产率生成核苷5'-磷酰胺酸盐。该反应途径与RNA加帽反应、DNA或RNA连接反应以及水解酶和核酸酶的催化机制非常相似,这些生物系统中的反应涉及共价酶-NMP(核苷5'-单磷酸)中间体的形成,这可能为酶促反应提供有价值的线索。

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