Regioselective syntheses of 7-nitro-7-deazapurine nucleosides and nucleotides for efficient PCR incorporation

Org Lett. 2005 Sep 1;7(18):3865-8. doi: 10.1021/ol051144r.

Abstract

Substitution at the C(7) position of purine nucleotides by a potent electron-withdrawing nitro group facilitates the cleavage of glycosidic bonds under alkaline conditions. This property is useful for sequence-specific cleavage of DNA containing these analogues. Here we describe the preparation of 7-deaza-7-NO(2)-dA and 7-deaza-7-NO(2)-dG using two different approaches, starting from 2'-deoxy-adenosine and 6-chloro-7-deaza-guanine, respectively. These modified nucleosides were converted to nucleotide triphosphates, each of which can replace the corresponding, naturally occurring triphosphate to support PCR amplification. [structure: see text]

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • DNA / chemistry
  • Deoxyadenine Nucleotides / chemical synthesis*
  • Deoxyguanine Nucleotides / chemical synthesis*
  • Molecular Structure
  • Purine Nucleosides / chemical synthesis
  • Purine Nucleosides / chemistry
  • Stereoisomerism
  • Structure-Activity Relationship

Substances

  • 7-deaza-7-nitro-dATP
  • 7-deaza-7-nitro-dGTP
  • Deoxyadenine Nucleotides
  • Deoxyguanine Nucleotides
  • Purine Nucleosides
  • DNA