Theoretical study of 9-beta-D-erythrofuranosyladenine and corresponding carbocyclic analogues. Evidence for a base-activated conformational lock

Akdag A., Carver C., McKee M., Schneller S.

JOURNAL OF PHYSICAL CHEMISTRY A, vol.106, no.46, pp.11254-11261, 2002 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 106 Issue: 46
  • Publication Date: 2002
  • Doi Number: 10.1021/jp021563v
  • Journal Name: JOURNAL OF PHYSICAL CHEMISTRY A
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.11254-11261
  • Middle East Technical University Affiliated: Yes

Abstract

The conformational surfaces of three nucleoside analogues have been investigated computationally, where an adenine is attached to a diol of tetrahydrofuran, a diol of cyclopentane, and a diol of cyclopentene. In each system, the lowest-energy conformer displays a conformational lock into the south position by an internal hydrogen bond between O2'H of the five-membered ring and the N3 nitrogen of adenine. When aqueous. solvation is accounted for by the PCM method, the preference for the locked conformer is diminished. A pseudorotation angle of 9-(trans-2',trans-3'dihydroxycyclopentyl)adenine has been determined to be 176.8degrees by fitting the measured (3)J(HH) values using PSEUROT which is in good agreement with the calculated value of 169.3degrees.