Water‐Medium Synthesis of Nucleoside 5′‐Polyphosphates. Issue 1 (19th June 2017)

• Record Type: Journal Article
• Authors: Depaix, Anaïs; Peyrottes, Suzanne; Roy, Béatrice
• Editors: Egli, Martin; Herdewijn, Piet; Matusda, Akira; Sanghvi, Yogesh S.
• Is Part Of: Current protocols in nucleic acid chemistry. Volume 69:Issue 1(2017)
• Page Start: 13.16.1
• Page End: 13.16.11
• Publication Date: 2017-06-19
• Subjects: nucleosides -- nucleotides -- phosphorylation -- synthetic methods -- water chemistry; Nucleic acids -- Laboratory manuals; Nucleic Acids -- chemical synthesis; Nucleic acids; Laboratory Manuals; Electronic books; Laboratory manuals; 572.8028
• DOI: 10.1002/cpnc.30
• Languages: English
• ISSNs: 1934-9270

Abstract

Abstract: This unit describes a one‐pot, two step synthesis of ribonucleoside 5′‐di‐ and 5′‐triphosphates, as well as their purification. The first step of the synthesis involves the activation of an unprotected ribonucleoside 5′‐monophosphate with 2‐chloro‐1, 3‐dimethylimidazolinium hexafluorophosphate and imidazole, in a mixture of water/acetonitrile. The resulting phosphorimidazolate intermediate is then treated with inorganic phosphate or pyrophosphate to afford the corresponding nucleoside 5′‐di‐ or 5′‐triphosphates. The attractive features of this strategy include the absence of protecting groups on the starting material and convenient set up (i.e., use of water, non‐dry solvents and reagents, commercially available sodium salts). © 2017 by John Wiley & Sons, Inc.