Stereoselective synthesis of 4′-selenonucleosides via seleno-Michael reaction as potent antiviral agents

Pramod K. Sahu; Gyudong Kim; Jinha Yu; Ji Yoon Ahn; Jayoung Song; Yoojin Choi; Xing Jin; Jin Hee Kim; Sang Kook Lee; Sunghyouk Park; Lak Shin Jeong

doi:10.1021/ol502899b

Stereoselective synthesis of 4′-selenonucleosides via seleno-Michael reaction as potent antiviral agents

Pramod K. Sahu, Gyudong Kim, Jinha Yu, Ji Yoon Ahn, Jayoung Song, Yoojin Choi, Xing Jin, Jin Hee Kim, Sang Kook Lee, Sunghyouk Park, Lak Shin Jeong

Department of Pharmaceutical Sciences

Research output: Contribution to journal › Article › peer-review

42 Scopus citations

Abstract

Based on the hypothesis that the bulky selenium atom, with 4p orbitals, can sterically hinder the approach of a cellular kinase to 5′-OH for phosphorylation, 4′-selenonucleosides with one-carbon homologation were designed and synthesized via a novel seleno-Michael reaction, with the stereoselectivity controlled by steric effects. 5′-Homo-4′-selenonucleosides (n = 2) demonstrated potent antiherpes simplex virus (HSV-1) activity, indicating that the bulky selenium atom might play a key role in preventing phosphorylation by cellular kinases, resulting in no antiviral activity.

Original language	English
Pages (from-to)	5796-5799
Number of pages	4
Journal	Organic Letters
Volume	16
Issue number	21
DOIs	https://doi.org/10.1021/ol502899b
State	Published - 7 Nov 2014

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© 2014 American Chemical Society.

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title = "Stereoselective synthesis of 4′-selenonucleosides via seleno-Michael reaction as potent antiviral agents",

abstract = "Based on the hypothesis that the bulky selenium atom, with 4p orbitals, can sterically hinder the approach of a cellular kinase to 5′-OH for phosphorylation, 4′-selenonucleosides with one-carbon homologation were designed and synthesized via a novel seleno-Michael reaction, with the stereoselectivity controlled by steric effects. 5′-Homo-4′-selenonucleosides (n = 2) demonstrated potent antiherpes simplex virus (HSV-1) activity, indicating that the bulky selenium atom might play a key role in preventing phosphorylation by cellular kinases, resulting in no antiviral activity.",

author = "Sahu, {Pramod K.} and Gyudong Kim and Jinha Yu and Ahn, {Ji Yoon} and Jayoung Song and Yoojin Choi and Xing Jin and Kim, {Jin Hee} and Lee, {Sang Kook} and Sunghyouk Park and Jeong, {Lak Shin}",

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year = "2014",

month = nov,

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doi = "10.1021/ol502899b",

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T1 - Stereoselective synthesis of 4′-selenonucleosides via seleno-Michael reaction as potent antiviral agents

AU - Sahu, Pramod K.

AU - Kim, Gyudong

AU - Yu, Jinha

AU - Ahn, Ji Yoon

AU - Song, Jayoung

AU - Choi, Yoojin

AU - Jin, Xing

AU - Kim, Jin Hee

AU - Lee, Sang Kook

AU - Park, Sunghyouk

AU - Jeong, Lak Shin

PY - 2014/11/7

Y1 - 2014/11/7

N2 - Based on the hypothesis that the bulky selenium atom, with 4p orbitals, can sterically hinder the approach of a cellular kinase to 5′-OH for phosphorylation, 4′-selenonucleosides with one-carbon homologation were designed and synthesized via a novel seleno-Michael reaction, with the stereoselectivity controlled by steric effects. 5′-Homo-4′-selenonucleosides (n = 2) demonstrated potent antiherpes simplex virus (HSV-1) activity, indicating that the bulky selenium atom might play a key role in preventing phosphorylation by cellular kinases, resulting in no antiviral activity.

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JO - Organic Letters

JF - Organic Letters

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ER -

Stereoselective synthesis of 4′-selenonucleosides via seleno-Michael reaction as potent antiviral agents

Abstract

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