Tetrahedron p. 4373 - 4382 (1993)
Update date:2022-08-02
Topics:
Gurjar
Kunwar
Reddy
Islam
Lalitha
Jagannadh
Rama Rao
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.
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(2011)