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

Yousef Ahmadibeni | Zendy; Chandravanu Dash | Zendy; Michael J. Hanley | Zendy; Stuart F.J. Le Grice | Zendy; Hitesh K. Agarwal | Zendy; Keykavous Parang | Zendy

Open Access

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

Author(s) -

Yousef Ahmadibeni,

Chandravanu Dash,

Michael J. Hanley,

Stuart F.J. Le Grice,

Hitesh K. Agarwal,

Keykavous Parang

Publication year - 2010

Publication title -

organic and biomolecular chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.923

H-Index - 146

eISSN - 1477-0539

pISSN - 1477-0520

DOI - 10.1039/b922846b

Subject(s) - methylene , chemistry , reverse transcriptase , nucleoside , cytidine , reagent , nucleotide , potency , rnase h , zidovudine , nucleoside analogue , nucleoside triphosphate , nucleoside reverse transcriptase inhibitor , human immunodeficiency virus (hiv) , stereochemistry , enzyme , biochemistry , medicinal chemistry , organic chemistry , rna , virology , biology , in vitro , gene , viral disease

A polymer-bound alpha,beta-methylene-beta-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-alpha,beta-methylene-beta-triphosphates. Among all the compounds, cytidine 5'-O-alpha,beta-methylene-beta-triphosphate inhibited RNase H activity of HIV-1 reverse transcriptase with a K(i) value of 225 microM.

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