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Article

Theoretical Study of 9-β-d-Erythrofuranosyladenine and Corresponding Carbocyclic Analogues. Evidence for a Base-Activated Conformational Lock

Supporting Info

Akin Akda

, Cynthia M. Carver, Michael L. McKee,* and Stewart W. Schneller*

Department of Chemistry, Auburn University, Auburn, Alabama 36849

J. Phys. Chem. A, 2002, 106 (46), pp 11254–11261

DOI: 10.1021/jp021563v

Publication Date (Web): October 23, 2002

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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 176.8° by fitting the measured ³J_HH values using PSEUROT which is in good agreement with the calculated value of 169.3°.

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