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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