Effect of change in nucleoside structure on the activation and antiviral activity of phosphoramidate derivatives

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Abstract

Changing the nucleoside group of a series of phosphoramidate derivatives affects the enzyme mediated hydrolysis rate of the compounds. d4T and AZT-substituted analogs were activated by enzymes such as lipases, esterases, and proteases. On the other hand, 3dT-substituted derivatives were comparatively less prone to hydrolysis under similar experimental conditions. From the experimental results, we propose that the most preferable nucleoside group for enzyme activation is d4T rather than AZT or 3dT. Additionally, we also observed that depending on the enzymes used the chiral selectivity of the enzymes for the phosphorus center of these phosphoramidate derivatives differed, demonstrating the importance of the nucleoside structure for this class of compounds. © 2005 Elsevier Ltd. All rights reserved.

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Venkatachalam, T. K., Samuel, P., Qazi, S., & Uckun, F. M. (2005). Effect of change in nucleoside structure on the activation and antiviral activity of phosphoramidate derivatives. Bioorganic and Medicinal Chemistry, 13(18), 5408–5423. https://doi.org/10.1016/j.bmc.2005.04.083

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