Effective Synthesis of 3′-Deoxy-3′-Azido Nucleosides for Antiviral and Antisense Ribonucleic Guanidine (RNG) Applications

Abstract

Two synthetic routes to 3′-deoxy-3′-azido nucleosides are described, one toward the synthesis of 3′-deoxy-3′-azidouridine and a second toward 3′-deoxy-3′-azidocytidine. The target compounds may serve as precursors to provide building blocks for use in automated synthesis of guanidine-linked RNA analogs (RNG) or oligonucleotide N3′→P5′ phosphoramidates. Moreover, the synthetic approaches are adaptable to the general synthesis of 3′-substituted 3′-deoxynucleosides for development of new antiviral drugs.

Keywords:

• Antisense
• RNA
• ribonucleic guanidine
• solid-phase synthesis
• nucleoside-3′-azido

Acknowledgments

Funding was provided by the Chemistry Program and Biology/Biotechnology Program at CSU Channel Islands. We thank Scott Duffer and the University of California Santa Barbara for assistance in obtaining spectral data. We also thank Tobin Streamland for assistance with experimentation.