The Crystal and Molecular Structure of 3′-Fluoro-3′-Deoxythymidine, a Potent Anti-HIV-1 Nucleoside

Abstract

The crystal structure of 3′-fluoro-3′-deoxythymidine (FDT), a nucleoside analogue with high potency against human immunodeficiency virus type 1 (HIV-1) in cell culture, has been determined as part of studies aimed at determining correlations between the molecular conformations of anti-HIV nucleosides and their potency. FDT crystallizes with four molecules in the asymmetric unit. The largest differences between the four molecules are in the conformations about the glycosidic bond, but they are otherwise surprisingly similar in conformation. All four molecules have C3′- exo/C2′- endo dideoxyribose ring conformations, very similar to that of one of the two molecules of 3′-azido-3′-deoxythymidine (AZT) in its crystal structure. Revised