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Synthesis and photophysical study of 2-fluorenyl-1,2,3-triazole-labeled 2’-deoxyuridine and its oligonucleotide

Seung Woo Hong and Gil Tae Hwang*
Department of Chemistry, Kyungpook National University, Daegu 702-701, South Korea
Fluorene is regarded as an important fluorophores. Because it has a good quantum yield and is less bulky than other commonly used fluorophores. We attached fluorene to 2’-deoxyuridine through ethynyl linker (UFL)) and observed good solvent dependent photophysical properties. In this study, we synthesize another fluorene labeled 2’-deoxyuridine linked by triazole group via copper catalyzed azide-alkyne cycloaddition (CuAAC). Here we prepared 2-fluorenyl-1,2,3-triazol-4-yl-2’-deoxyuridine (UFT) and inserted it at the central position of an oligonucleotide (ODN). UFT displays different fluorescence intensities and emission maxima in different solvents, indicating its potential for application as an environmentally sensitive probe. However ODN containing UFT did not exhibit selective thermal stability and fluorescence changes upon duplex formation with matched and single-base mismatched targets. This highlighted the importance of selecting the appropriate linker to connect the fluorophore to the nucleobase when developing such DNA probe.

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