Solid State and Solution Structure and Conformation of The Antiviral Acyclonucleoside 9-[4-Hydroxy-2-(hydroxymethyl)-butyl]guanine

Abstract

The title compound, 9-[4-hydroxy-2-(hydroxymethyl)-butyl]guanine (2HM-HBG), crystallizes in the triclinic space group P1 with two independent molecules and one water molecule in the asymmetric unit. The acyclic chain of one molecule is in the fully extended form, and the other partially folded. The orientation of this chain with respect to the base corresponds to the conformation syn in natural nucleosides. The conformations of the two molecules were compared with the solution conformation from an analysis of the ¹H-¹H vicinal coupling constants. The comportment of some acyclonucleosides in several enzyme systems is examined in relation to their existence in folded or extended forms.