Design, Synthesis and Cellular Metabolism Study of 4′-Selenonucleosides

4′-Seleno-homonucleosides were synthesized as next generation nucleosides, and their cellular phosphorylation was studied to confirm the hypothesis that bulky selenium atom can sterically hinder the approach of cellular nucleoside kinase to the 5′-OH for phosphorylation.

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4´-Seleno-homo-pyrimidine and purine nucleosides with one-carbon homologation, were synthesized through a tandem seleno-Michael addition-SN2 ring cyclization. The cellular metabolism study via LC-MS analysis demonstrated that they were phosphorylated by cellular nucleoside kinases, resulting in anticancer activity. The bulky selenium atom played a key role in deciding the phosphorylation by cellular nucleoside kinases.

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Lak Shin Jeong

Professor, Seoul National University

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