Gurjar, M. K. ; Kunwar, A. C. ; Reddy, D. V. ; Islam, A. ; Lalitha, S. V. S. ; Jagannadh, B. ; Rama Rao, A. V. (1993) Syntheses and conformational studies on AZT and its deuterated analogues Tetrahedron, 49 (20). pp. 4373-4382. ISSN 0040-4020
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Official URL: http://linkinghub.elsevier.com/retrieve/pii/S00404...
Related URL: http://dx.doi.org/10.1016/S0040-4020(01)85754-9
Abstract
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.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to Elsevier Science. |
| Keywords: | 3'-azido-3'-deutero-thymidine; (2'R)-3'-azido-3'-deoxy-2'-deuterothymidine; Nuclear Magentic Resonance; Synthesis; Conformation |
| ID Code: | 38847 |
| Deposited On: | 05 May 2011 06:18 |
| Last Modified: | 05 May 2011 06:18 |
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