Synthesis of nucleoside Di- and triphosphates and dinucleoside polyphosphates with cycloSal-nucleotides

J Org Chem. 2009 Apr 17;74(8):3024-30. doi: 10.1021/jo802348h.

Abstract

A new and efficient method for the synthesis of nucleoside di- and triphosphates as well as dinucleoside polyphosphates (Np(n)N') is described. 5-Acceptor-substituted (5-nitro and 5-chloro) cycloSal-nucleotides are used as starting material that were reacted with a variety of phosphate nucleophiles as pyrophosphate or nucleotides to the corresponding products in short times and very good yields. After consumption of the starting cycloSal-phosphate triester, first the protecting groups were cleaved and finally the products were isolated after RP-column chromatography. Examples are shown for all five pyrimidine and purine bases found in natural nucleosides as well as one non-natural pyrimidine base to prove that the method can be applied generally.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Chromatography, High Pressure Liquid
  • Dinucleoside Phosphates / chemical synthesis*
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Nucleosides / chemical synthesis*
  • Nucleotides / chemical synthesis*
  • Ribonucleotides / chemistry*

Substances

  • Dinucleoside Phosphates
  • Nucleosides
  • Nucleotides
  • Ribonucleotides