7-deaza-2'-deoxyxanthosine: nucleobase protection and base pairing of oligonucleotides

Nucleosides Nucleotides Nucleic Acids. 2007;26(6-7):737-41. doi: 10.1080/15257770701490837.

Abstract

Oligonucleotides containing 7-deaza-2'-deoxyxanthosine (1) and 2'-deoxyxanthosine (2) were prepared. The 2-(4-nitrophenyl)ethyl group is applicable for 7-deazaxanthine protection that is removed with DBU by beta-elimination, while the deprotection of the allyl residue with Pd (0) catalyst failed. Contrarily, the allyl group was found to be an excellent protecting group for 2'-deoxyxanthosine (2). The base pairing of nucleosides 1 and 2 with the four canonical DNA constituents as well as with 3 within the 12-mer duplexes is studied.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Base Pairing*
  • Deoxyribonucleosides / chemistry*
  • Nucleosides / chemistry*
  • Oligonucleotides / chemistry*
  • Organophosphorus Compounds / chemical synthesis
  • Organophosphorus Compounds / chemistry
  • Transition Temperature

Substances

  • 7-deaza-2'-deoxyxanthosine
  • Deoxyribonucleosides
  • Nucleosides
  • Oligonucleotides
  • Organophosphorus Compounds