Journal
ORGANIC LETTERS
Volume 16, Issue 21, Pages 5796-5799Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol502899b
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- Seoul National University
- Next Generation Leaders Training for the new faculty
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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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