Syntheses and conformational studies on AZT and its deuterated analogues

Article abstract of DOI:10.1016/S0040-4020(01)85754-9

The NMR spectrum of 3′-azido-3′-deoxythymidine (AZT) in aqueous solution provides sum of some of the proton-proton coupling constants. This limitation precludes the determination of the pseudorotational parameters of the sugar ring. Selective deuteration alleviates this problem. The synthesis of 2′-deutero and 3′-deutero- AZT have been described for the first time starting from D-xylose and β-thymidine respectively. NMR study of these analogues in aqueous solutions shows that almost equal amount of C-2′-endo and C-3′-endo species exist in equilibrium.