A short path synthesis of [13C/15N] multilabeled pyrimidine nucleosides starting from glucopyranose nucleosides

J Org Chem. 2003 Mar 7;68(5):1867-71. doi: 10.1021/jo0205098.

Abstract

The synthesis of fully [13C/15N] labeled pyrimidine nucleosides has been achieved from 13C-glucose and labeled nucleobases. The reaction scheme leads directly to the protected nucleosides without the need for the inversion of configuration of C-3 of 13C-glucose. This was achieved by an oxitative ring-opening reaction removing the carbon with the wrong configuration.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carbon Isotopes
  • Chemistry, Organic / methods
  • Chromatography, Thin Layer
  • Cyclization
  • Glucose / chemistry*
  • Indicators and Reagents
  • Molecular Structure
  • Nitrogen Isotopes
  • Nuclear Magnetic Resonance, Biomolecular
  • Pyrimidine Nucleosides / chemical synthesis*
  • Structure-Activity Relationship
  • Uracil / chemical synthesis

Substances

  • Carbon Isotopes
  • Indicators and Reagents
  • Nitrogen Isotopes
  • Pyrimidine Nucleosides
  • Uracil
  • Glucose