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

doi:10.1039/b922846b

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 journal › Article › peer-review

7 Scopus citations

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 K_i value of 225 μM.

Original language	English (US)
Pages (from-to)	1271-1274
Number of pages	4
Journal	Organic and Biomolecular Chemistry
Volume	8
Issue number	6
DOIs	https://doi.org/10.1039/b922846b
State	Published - 2010
Externally published	Yes

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Organic Chemistry
Biochemistry

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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.",

author = "Y. Ahmadibeni and C. Dash and Hanley, {M. J.} and {Le Grice}, {S. F J} and Agarwal, {H. K.} and K. Parang",

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T1 - Synthesis of nucleoside 5′-O-α,β-methylene-β- triphosphates and evaluation of their potency towards inhibition of HIV-1 reverse transcriptase

AU - Ahmadibeni, Y.

AU - Dash, C.

AU - Hanley, M. J.

AU - Le Grice, S. F J

AU - Agarwal, H. K.

AU - Parang, K.

PY - 2010

Y1 - 2010

N2 - 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.

AB - 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.

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DO - 10.1039/b922846b

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SN - 1477-0520

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EP - 1274

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 6

ER -

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

Abstract

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