New synthesis of 5-carboxy-2'-deoxyuridine and its incorporation into synthetic oligonucleotides

Nucleosides Nucleotides Nucleic Acids. 2003 May-Aug;22(5-8):1073-5. doi: 10.1081/NCN-120022739.

Abstract

5-Carboxy-2'-deoxyuridine is a methyl oxidation product of thymidine. It can be formed by the menadione-mediated photosensitization of thymidine in aerated aqueous solution. Here in we present a new four-step synthesis of the 5-carboxy-2'-deoxyuridine phosphoramidite building block based on the alkaline hydrolysis of 5-trifluoromethyl-2'-deoxyuridine. The phosphoramidite derivative has been incorporated at defined sites into oligonucleotides using the solid phase synthesis approach.

MeSH terms

  • Amides
  • Deoxyuridine / analogs & derivatives*
  • Deoxyuridine / chemical synthesis*
  • Deoxyuridine / chemistry
  • Hydrolysis
  • Indicators and Reagents
  • Molecular Structure
  • Oligodeoxyribonucleotides / chemical synthesis*
  • Oligodeoxyribonucleotides / chemistry
  • Phosphoric Acids

Substances

  • Amides
  • Indicators and Reagents
  • Oligodeoxyribonucleotides
  • Phosphoric Acids
  • 5-carboxy-2'-deoxyuridine
  • phosphoramidic acid
  • Deoxyuridine