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

2002-11-01
Akdağ, Akın
McKee, ML
Schneller, SW
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.
JOURNAL OF PHYSICAL CHEMISTRY A

Suggestions

Theoretical investigation of hydroxytyrosol and its radicals
Erkoc, F; Keskin, N; Erkoç, Şakir (Elsevier BV, 2003-05-05)
The structural and electronic properties of hydroxytyrosol, its three radical isomers, and its three analogues hydroxytyrosol-dihydroxyl isomers have been investigated theoretically by performing semi-empirical self-consistent field molecular orbital theory calculations. The geometry of the systems have been optimized and the electronic properties have been calculated at the level of AMI method.
Theoretical investigation of quercetin and its radical isomers
Erkoc, E; Erkoc, F; Keskin, N (Elsevier BV, 2003-08-01)
The structural and electronic properties of quercetin and its five radical isomers have been investigated theoretically by performing semi-empirical molecular orbital theory calculations. The geometry of the systems have been optimized and the electronic properties of the systems considered have been calculated by semi-empirical self-consistend-field molecular orbital theory at the level AM1 within UHF formalism in their ground state. Conclusions have been drawn by comparing with experimental results.
Theoretical investigation of melatonin and its hydroxy isomers
Erkoc, A; Erkoc, F; Keskin, N (Elsevier BV, 2002-07-05)
The structural and electronic properties of melatonin and its six hydroxy isomers have been investigated theoretically by performing semi-empirical and ab initio molecular orbital theory calculations. The geometry of the systems has been optimized considering the semi-empirical molecular orbital theory at the level of AM I, and the electronic properties of the systems have been calculated by ab initio RHF including full MP2 correlation correction in their ground state. Conclusions were drawn by comparing wi...
Quantum chemical treatment of cyanogen azide and its univalent and divalent ionic forms
Türker, Burhan Lemi; Atalar, Taner (Elsevier BV, 2008-05-30)
An explosive material, cyanogen azide (CN4) and its univalent and divalent anionic and cationic forms have been studied quantum chemically by using different theoretical approaches. In this study, the structures considered have been screened for their relative stabilities. Also, they have been investigated whether the charged forms play a role in the usual explosion process or any electrical charging during storage cause explosion. Various quantum chemical properties are obtained and discussed. It has been ...
STRUCTURAL STABILITY AND ENERGETICS OF SI4 ISOMERS - TOTAL ELECTRONIC-ENERGY CALCULATION
Katırcıoğlu, Şenay (Elsevier BV, 1991-09-20)
The structural stability and energetics of Si4 isomers have been investigated by using an empirical tight-binding (ETB) method. It has been found that the most stable Si4 microcluster is an exact tetrahedron with T(d) symmetry.
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.