Preparation of synthetically challenging nucleotides using cyanoethyl P-imidazolides and microwaves

Org Lett. 2012 Sep 21;14(18):4782-5. doi: 10.1021/ol302071f. Epub 2012 Sep 11.

Abstract

We describe a general method for the elongation of nucleoside oligophosphate chains by means of cyanoethyl (CE) phosphorimidazolides. Though the method requires a phosphorylation and subsequent deprotection reaction, both steps could be achieved in one pot without isolation/purification of the initial phosphorylation product. We have also found that pyrophosphate bond formation by this method is significantly accelerated by microwave irradiation.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Imidazoles / chemistry*
  • Indicators and Reagents
  • Microwaves*
  • Molecular Structure
  • Nitriles / chemistry*
  • Nucleotides / chemical synthesis*
  • Nucleotides / chemistry

Substances

  • Imidazoles
  • Indicators and Reagents
  • Nitriles
  • Nucleotides