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

Research output: Contribution to journalArticlepeer-review

38 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 languageEnglish
Pages (from-to)5796-5799
Number of pages4
JournalOrganic Letters
Volume16
Issue number21
DOIs
StatePublished - 7 Nov 2014

Bibliographical note

Publisher Copyright:
© 2014 American Chemical Society.

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