Synthesis of 2′-Deoxyuridine and 2′-Deoxycytidine Nucleosides Bearing Bipyridine and Terpyridine Ligands at Position 5

Abstract

A methodology for the syntheses of pyrimidine (C or U) 2-deoxyribonucleosides bearing bipyridine or terpyridine ligands attached via acetylene or phenylene linkers was developed based on single step cross-coupling reactions of unprotected 5-iodopyrimidine nucleosides with bipyridine or terpyridine acetylenes of phenyl boronates. The Sonogashira reactions with acetylenes were performed in DMF, while the Suzuki reactions with boronates in water­-acetonitrile mixtures. Photophysical properties of the title modified nucleosides have been studied and (2,2′-bipyridin-5-yl)ethynyl or (2,2′-bipyridin-5-yl)phenyl derivatives exerting absorption at >300 nm and bright emission at 421-451 nm were selected as the best candidates for luminescent DNA labeling.

Key words

nucleosides - pyrimidines - bipyridines - N-ligands - cross-coupling reactions

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Vrábel M., Horáková P., Pivoňková H., Kalachova L., Černocká H., Cahová H., Pohl R., Šebest P., Havran L., Hocek M., Fojta M.; Chem. Eur. J.; 2008, in press