Structure and conformational analysis of the anti-HIV AZT 5′-aminocarbonylphosphonate prodrug using DFT methods

► The phosphonate prodrug studied offers an excellent potential as alternative to AZT. ► The 84 most energetically favourable conformers were identified by DFT methods. ► The increment in the ring puckering produces a higher flexibility than in AZT. ► The high charge on the oxygen's chain could explain the high activity of this prodrug. ► The phosphonate chain has little influence in the charge distribution on the rings.