Nucleoside and nucleotide analogues by catalyst free Huisgen nitrile oxide-alkyne 1,3-dipolar cycloaddition

Org Biomol Chem. 2010 Jan 21;8(2):391-7. doi: 10.1039/b917450h. Epub 2009 Oct 28.

Abstract

An efficient, catalyst free, 1,3-dipolar cycloaddition strategy to conjugate nucleosides and nucleotides with isoxazoles under atmospheric conditions and in an aqueous environment is reported. The protocol involves chloramine-T as a practical reagent to induce in situ nitrile oxide formation and the alkyne partner is attached to the sugar residue or the nucleobase. The reactions are regiospecific, fast and high yielding.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkynes / chemistry*
  • Carbohydrates / chemistry
  • Catalysis
  • Isoxazoles / chemical synthesis
  • Isoxazoles / chemistry
  • Nitriles / chemistry*
  • Nucleosides / chemistry*
  • Nucleotides / chemistry*
  • Oxides / chemistry*
  • Solutions

Substances

  • Alkynes
  • Carbohydrates
  • Isoxazoles
  • Nitriles
  • Nucleosides
  • Nucleotides
  • Oxides
  • Solutions