An efficient oxidizing reagent for the synthesis of mixed backbone oligonucleotides via the H-phosphonate approach

Bioorg Med Chem. 2003 Apr 3;11(7):1419-31. doi: 10.1016/s0968-0896(02)00615-6.

Abstract

The mixture of carbon tetrachloride, N-methyl morpholine (NMM), pyridine and water in acetonitrile has been exploited for the oxidation of dinucleoside H-phosphonate diesters to the corresponding phosphates. The system is found to be inert to the phosphoramidate (P-N) and the phosphorothioate (P-S) linkages and has successfully been applied to the solid phase synthesis of mixed-backbone oligonucleotides (MBOs).

MeSH terms

  • Chromatography, High Pressure Liquid
  • Indicators and Reagents
  • Magnetic Resonance Spectroscopy
  • Oligonucleotides / chemical synthesis*
  • Organophosphonates / chemistry*
  • Oxidants / chemistry*
  • Oxidation-Reduction
  • Spectrometry, Mass, Electrospray Ionization

Substances

  • Indicators and Reagents
  • Oligonucleotides
  • Organophosphonates
  • Oxidants