A locked derivative of 8-aza-7-deazaadenosine

Acta Crystallogr C. 2008 Aug;64(Pt 8):o467-70. doi: 10.1107/S0108270108021628. Epub 2008 Jul 26.

Abstract

The title compound [systematic name: (1S,3S,4R,7S)-3-(4-amino-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-1-hydroxymethyl-2,5-dioxabicyclo[2.2.1]heptan-7-ol], C(11)H(13)N(5)O(4), belongs to a family of nucleosides with modifications in both the sugar and nucleobase moieties: these modifications are known to increase the thermodynamic stability of DNA and RNA duplexes. There are two symmetry-independent molecules in the asymmetric unit that differ significantly in conformation, and both exhibit a high-anti conformation about the N-glycosidic bond, with chi torsion angles of -85.4 (3) and -87.4 (3) degrees . The sugar C atom attached to the nucleobase N atom is -0.201 (4) and 0.209 (4) A from the 8-aza-7-deazaadenine skeleton plane in the two molecules. The molecules are assembled into layers via hydrogen bonds and pi-pi stacking interactions between the modified nucleobases.

MeSH terms

  • Crystallography, X-Ray
  • Deoxyadenosines / chemistry*
  • Hydrogen Bonding
  • Models, Molecular
  • Molecular Structure

Substances

  • Deoxyadenosines
  • 4-aminopyrazolopyrimidine-2'-deoxyribofuranoside