Efficient synthesis of the tRNA nucleoside preQ0, 7-cyano-7-deazaguanosine, via microwave-assisted iodo→carbonitrile exchange

Chem Biodivers. 2010 Oct;7(10):2616-21. doi: 10.1002/cbdv.201000239.

Abstract

The naturally occurring tRNA nucleoside preQ(0), 7-cyano-7-deazaguanosine, which is a central intermediate for other natural occurring 7-deazapurine nucleosides was synthesized via a copper(I)-ion-mediated iodo→carbonitrile exchange. The reaction was performed on the easily accessible 7-iodo-7-deazaguanosine under microwave conditions. The overall reaction yield was 30% starting with the glycosylation reaction of the nucleobase. Corresponding 2'-deoxyribonucleosides were prepared following the same route.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Copper / chemistry
  • Glycosylation
  • Guanosine / analogs & derivatives*
  • Guanosine / chemical synthesis
  • Guanosine / chemistry
  • Magnetic Resonance Spectroscopy
  • Microwaves*
  • Molecular Structure
  • Nitriles / chemistry*
  • Nucleoside Q / chemical synthesis*
  • Nucleoside Q / chemistry
  • RNA, Transfer / chemical synthesis*
  • RNA, Transfer / chemistry

Substances

  • 7-cyano-7-deazaguanosine
  • 7-iodo-7-deazaguanosine
  • Nitriles
  • Guanosine
  • Nucleoside Q
  • Copper
  • RNA, Transfer