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

Date

2002-11-01

Author

Akdağ, Akın
McKee, ML
Schneller, SW

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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.

Subject Keywords

S-Adenosylhomocysteine hydrolase, Pseudorotational equilibrium, Sugar ring, Nucleic-acids, Molecular-structure, Antiviral activity, L-homocysteine hydrolase, Density-functional calculations, Center-dot-n, Spin-coupling-constants

URI

https://hdl.handle.net/11511/56980

Journal

JOURNAL OF PHYSICAL CHEMISTRY A

DOI

https://doi.org/10.1021/jp021563v

Collections

Department of Chemistry, Article

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Citation Formats

A. Akdağ, M. McKee, and S. Schneller, “Theoretical study of 9-beta-D-erythrofuranosyladenine and corresponding carbocyclic analogues. Evidence for a base-activated conformational lock,” JOURNAL OF PHYSICAL CHEMISTRY A, pp. 11254–11261, 2002, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/56980.