Lessons from the Pseudorotational Cycle: Conformationally Rigid AZT Carbocyclic Nucleosides and Their Interaction with Reverse Transcriptase

Victor E. Marquez Laboratory of Medicinal Chemistry, Division of Basic Sciences, Washington, DC, 20375

Abdallah Ezzitouni Laboratory of Medicinal Chemistry, Division of Basic Sciences, Washington, DC, 20375

Pamela Russ Laboratory of Medicinal Chemistry, Division of Basic Sciences, Washington, DC, 20375

Maqbool A. Siddiqui Laboratory of Medicinal Chemistry, Division of Basic Sciences, Washington, DC, 20375

Harry Ford Jr Laboratory of Medicinal Chemistry, Division of Basic Sciences, Washington, DC, 20375

Ron J. Feldman Experimental Retrovirology Section, Medicine Branch Division of Clinical Sciences National Cancer Institute, National Institutes of Health, Bethesda, MD, 20892

Hiroaki Mitsuya Experimental Retrovirology Section, Medicine Branch Division of Clinical Sciences National Cancer Institute, National Institutes of Health, Bethesda, MD, 20892

Clifford George Laboratory for the Structure of Matter, Naval Research Laboratory, Washington, DC, 20375

Joseph J. Barchi Jr Laboratory of Medicinal Chemistry, Division of Basic Sciences, Washington, DC, 20375

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Abstract

Two conformationally locked carba-AZT nucleoside 5′-triphosphates built on a rigid bicyclo[3.1.0]hexane template showed exclusive Northern (₂E) and Southern (₃E) conformations, respectively. Inhibition of reverse transcriptase (RT) occurred selectively with the Northern carba-AZX triphosphate.

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Lessons from the Pseudorotational Cycle: Conformationally Rigid AZT Carbocyclic Nucleosides and Their Interaction with Reverse Transcriptase

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Lessons from the Pseudorotational Cycle: Conformationally Rigid AZT Carbocyclic Nucleosides and Their Interaction with Reverse Transcriptase

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