Structural effects on the phosphorylation of 3-substituted 1-β-d-ribofuranosyl-1,2,4-triazoles by human adenosine kinase

Sidath C. Kumarapperuma; Yanjie Sun; Marjan Jeselnik; Kiwon Chung; William B. Parker; Colleen B. Jonsson; Jeffrey B. Arterburn

doi:10.1016/j.bmcl.2007.03.018

Structural effects on the phosphorylation of 3-substituted 1-β-d-ribofuranosyl-1,2,4-triazoles by human adenosine kinase

Sidath C. Kumarapperuma, Yanjie Sun, Marjan Jeselnik, Kiwon Chung, William B. Parker, Colleen B. Jonsson, Jeffrey B. Arterburn

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Abstract

The conversion of ribavirin to the monophosphate by adenosine kinase is the rate-limiting step in activation of this broad spectrum antiviral drug. Variation of the 3-substituents in a series of bioisosteric and homologated 1-β-d-ribofuranosyl-1,2,4-triazoles has marked effects on activity with the human adenosine kinase, and analysis of computational descriptors and binding models offers insight for the design of novel substrates.

Original language	English (US)
Pages (from-to)	3203-3207
Number of pages	5
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	17
Issue number	11
DOIs	https://doi.org/10.1016/j.bmcl.2007.03.018
State	Published - Jun 1 2007
Externally published	Yes

Bibliographical note

Funding Information:
This work was supported by Department of Defense USAMRC Grant No. W81XWH-04-C-0055 (C.J.), and NIH INBRE RR016480 (J.A.).

Keywords

Adenosine kinase
Antiviral
Bioisostere
Ribavirin
Triazole

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title = "Structural effects on the phosphorylation of 3-substituted 1-β-d-ribofuranosyl-1,2,4-triazoles by human adenosine kinase",

abstract = "The conversion of ribavirin to the monophosphate by adenosine kinase is the rate-limiting step in activation of this broad spectrum antiviral drug. Variation of the 3-substituents in a series of bioisosteric and homologated 1-β-d-ribofuranosyl-1,2,4-triazoles has marked effects on activity with the human adenosine kinase, and analysis of computational descriptors and binding models offers insight for the design of novel substrates.",

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note = "Funding Information: This work was supported by Department of Defense USAMRC Grant No. W81XWH-04-C-0055 (C.J.), and NIH INBRE RR016480 (J.A.).",

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AU - Kumarapperuma, Sidath C.

AU - Sun, Yanjie

AU - Jeselnik, Marjan

AU - Chung, Kiwon

AU - Parker, William B.

AU - Jonsson, Colleen B.

AU - Arterburn, Jeffrey B.

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KW - Antiviral

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KW - Triazole

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Structural effects on the phosphorylation of 3-substituted 1-β-d-ribofuranosyl-1,2,4-triazoles by human adenosine kinase

Abstract

Bibliographical note

Keywords

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