Synthesis of isotopically labeled D-[1'-13C]ribonucleoside phosphoramidites

Carbohydr Res. 2001 Mar 9;331(1):83-90. doi: 10.1016/s0008-6215(00)00327-x.

Abstract

The preparation of fully protected labeled diisopropylamino-beta-cyanoethyl-[1'-13C]ribonucleoside phosphoramidites with regioisomeric purity is described. We demonstrated in this paper that a regioselective 2'-O-silylation, through a 3',5'-O-di-tert-butylsilanediyl protection, has been applied for the synthesis of [1'-13C]ribonucleoside phosphoramidite units. This method allowed us to obtain only the desired 2'-O-silyl-3'-O-phosphoramidites avoiding the undesired 3'-O-silyl-2'-O-phosphoramidite nucleosides isolated by standard procedures. This is a suitable procedure to RNA precursors with respect to the isotope-containing precursors.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carbon Isotopes
  • Indicators and Reagents
  • Isotope Labeling / methods
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Oligoribonucleotides / chemical synthesis
  • Organophosphorus Compounds / chemical synthesis*
  • Organophosphorus Compounds / chemistry
  • RNA / chemical synthesis
  • Ribonucleosides / chemical synthesis*
  • Ribonucleosides / chemistry

Substances

  • Carbon Isotopes
  • Indicators and Reagents
  • Oligoribonucleotides
  • Organophosphorus Compounds
  • Ribonucleosides
  • RNA