Literature DB >> 16095286

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

Jigang Zhu1, Bo Han, Hua Fu, Yuyang Jiang, Yufen Zhao.   

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.

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Year:  2005        PMID: 16095286     DOI: 10.1021/jo050716i

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  2 in total

Review 1.  Synthesis of nucleoside phosphate and phosphonate prodrugs.

Authors:  Ugo Pradere; Ethel C Garnier-Amblard; Steven J Coats; Franck Amblard; Raymond F Schinazi
Journal:  Chem Rev       Date:  2014-08-21       Impact factor: 60.622

2.  Synthesis of nucleoside mono-, di-, and triphosphoramidates from solid-phase cyclosaligenyl phosphitylating reagents.

Authors:  Yousef Ahmadibeni; Rakesh K Tiwari; Gongqin Sun; Keykavous Parang
Journal:  Org Lett       Date:  2009-05-21       Impact factor: 6.005

  2 in total

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