Synthesis 2009(1): 105-112  
DOI: 10.1055/s-0028-1083266
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

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

Lubica Kalachova, Radek Pohl, Michal Hocek*
Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Gilead & IOCB Research Center, Flemingovo nám. 2, 16610 Prague 6, Czech Republic
Fax: +420(2)20183559; e-Mail: hocek@uochb.cas.cz;
Further Information

Publication History

Received 3 November 2008
Publication Date:
12 December 2008 (online)

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.

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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