Synthesis of Nucleoside 5′-O-α,β-methylene-β-triphosphates and Evaluation of Their Potency Towards Inhibition of HIV-1 Reverse Transcriptase

Authors

Yousef Ahmadibeni, University of Rhode IslandFollow
Chandravanu Dash, Meharry Medical CollegeFollow
M. J. Hanley, Millennium Pharmaceut Inc
S. F. J. Le Grice, National Cancer Institute, Bethesda, MDFollow
Hitesh K. Agarwal, Ohio State UniversityFollow
Keykavous Parang, Chapman UniversityFollow

Document Type

Article

Publication Date

2010

Abstract

A polymer-bound α,β-methylene-β-triphosphitylating reagent was synthesized and subjected to reactions with unprotected nucleosides, followed by oxidation, deprotection of cyanoethoxy groups, and acidic cleavage to afford nucleoside 5′-O-α,β-methylene-β-triphosphates. Among all the compounds, cytidine 5′-O-α,β-methylene-β-triphosphate inhibited RNase H activity of HIV-1 reverse transcriptase with a Ki value of 225 μM.

Comments

This is a pre-copy-editing, author-produced PDF of an article accepted for publication in Organic & Biomolecular Chemistry, volume 8, issue 6, 2010following peer review. The definitive publisher-authenticated version is available online at DOI: 10.1039/b922846b.

Recommended Citation

Ahmadibeni, Y., C. Dash, M. J. Hanley, S. F. J. Le Grice, H. K. Agarwal, and K. Parang. "Synthesis of nucleoside 5′-O-α, β-methylene-β-triphosphates and evaluation of their potency towards inhibition of HIV-1 reverse transcriptase." Organic & biomolecular chemistry 8, no. 6 (2010): 1271-1274.
doi: 10.1039/b922846b

Copyright

Royal Society of Chemistry