Molecular orbital studies on nucleoside antibiotics X. Conformation of nebularine and isoguanosine

Abstract

Conformational properties of two nucleoside analogs, namely nebularine and isoguanosine have been investigated by using PCILO (Perturbative Configuration Interaction using Localized Orbitals) method. Nebularine (9-β-ribofurnosyl purine) is a naturally occurring purine nucleoside which is structurally similar to adenosine and it inhibits the growth of tumor cells and influenza B virus. Isoguanosine is one of the two naturally occurring analogs of guanosine. Both C2′-endo and C3′-endo sugar puckerings have been considered for both the molecules with preselected values of torsion angles around C2′–O2′ and C5′–O5′ bonds. The results indicate that nebularine has conformational preferences very similar to those of its parent nucleoside, adenosine; whereas the conformational properties of isoguanosine are very different from those of guanosine as well as adenosine. The important implications of these results have been discussed in terms of the biological activity of these molecules.