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Issue 6, 2010
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Synthesis of nucleoside 5′-O-α,β-methylene-β-triphosphates and evaluation of their potency towards inhibition of HIV-1 reverse transcriptase

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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.

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

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Publication details

The article was received on 02 Nov 2009, accepted on 21 Dec 2009 and first published on 13 Jan 2010


Article type: Communication
DOI: 10.1039/B922846B
Citation: Org. Biomol. Chem., 2010,8, 1271-1274
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    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 and K. Parang, Org. Biomol. Chem., 2010, 8, 1271
    DOI: 10.1039/B922846B

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