Conformation of 3-Substituted Purine Nucleoside Studied By X-Ray Crystallography and Theoretical Calculations
- 1 July 1994
- journal article
- research article
- Published by Taylor & Francis in Nucleosides and Nucleotides
- Vol. 13 (6-7) , 1327-1335
- https://doi.org/10.1080/15257779408012155
Abstract
The molecular conformation of 3-methyl-3-deazainosine has been investigated by X-ray crystallographic and theoretical studies. In the crystal state the molecule has the high anti conformation about the glycosidic bond with the torsion angle of −79°. The sugar ring is puckered with C(1′)-exo, C(2′)-endo, and the conformation about the C(4′)-C(5′) bond is gauche-trans. The quantum chemical calculations show that the lowest energy conformation about the glycosidic bond of 3-methyl-3-deazainosine is anti shifted to high anti, whereas in inosine the syn conformation is stable as well as the anti conformation.Keywords
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