An ab initio study on ribo and deoxy-ribo models for nucleosides and nucleotides

An exploratory set of ab initio molecular orbital computations were carried out on various conformations of ribose and deoxy-ribose model compounds to establish the nature of possible interactions between the 5'-hydroxyl and the oxygen of the ribose ring. Moreover, the investigation was extended to the hydrogen bonding between the two adjacent hydroxyls 2'- and 3'- to expl ore their effect on the stabilization of the whole system. The consistent p resence of a rather unusual weak hydrogen bond between the proton of C-2'-H and the O-5' Of the hydroxy methyl group for the g(-)g(-) conformation of the-CH2-OH functional group has been studied by using Bader's atoms in mole cules (AIM) method. (C) 1999 Elsevier Science B.V. All rights reserved.