SYNTHESES AND CONFORMATIONAL STUDIES ON AZT AND ITS DEUTERATED ANALOGS

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 beta-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.