Synthesis of nucleoside 5′-O-α,β-methylene-β- triphosphates and evaluation of their potency towards inhibition of HIV-1 reverse transcriptase

Y. Ahmadibeni, C. Dash, M. J. Hanley, S. F J Le Grice, H. K. Agarwal, K. Parang

Research output: Contribution to journalArticle

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.

Original languageEnglish (US)
Pages (from-to)1271-1274
Number of pages4
JournalOrganic and Biomolecular Chemistry
Volume8
Issue number6
DOIs
StatePublished - 2010
Externally publishedYes

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Biochemistry

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