7-Deaza-2'-deoxy-7-propynylguanosine

Acta Crystallogr C. 2004 Jul;60(Pt 7):o489-91. doi: 10.1107/S0108270104011552. Epub 2004 Jun 22.

Abstract

The title compound, C14H16N4O4, adopts the anti conformation at the glycosylic bond [chi -117.1 (5) degrees]. The sugar pucker of the 2'-deoxyribofuranosyl moiety is C2'-endo-C3'-exo, 2T3 (S-type). The orientation of the exocyclic C4'-C5' bond is +sc (gauche). The propynyl group is linear and coplanar with the nucleobase moiety. The structure of the compound is stabilized by several hydrogen bonds (N-H...O and O-H...O), leading to the formation of a multi-layered network. The nucleobases, as well as the propynyl groups, are stacked. This stacking might cause the extraordinary stability of DNA duplexes containing this compound.

MeSH terms

  • Aza Compounds / chemistry*
  • Crystallography, X-Ray
  • Deoxyguanosine / analogs & derivatives*
  • Deoxyguanosine / chemistry
  • Hydrogen Bonding
  • Molecular Structure

Substances

  • Aza Compounds
  • Deoxyguanosine