Water-Medium Synthesis of Nucleoside 5'-Polyphosphates

Curr Protoc Nucleic Acid Chem. 2017 Jun 19:69:13.16.1-13.16.11. doi: 10.1002/cpnc.30.

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.

Keywords: nucleosides; nucleotides; phosphorylation; synthetic methods; water chemistry.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Imidazoles / chemistry
  • Nucleosides / chemical synthesis*
  • Nucleosides / chemistry
  • Polyphosphates / chemistry*

Substances

  • Imidazoles
  • Nucleosides
  • Polyphosphates