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Nucleic Acids Symposium Series 2004 48(1):75-76; doi:10.1093/nass/48.1.75
© 2004 by Oxford University Press
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Synthesis and properties of fluorescent-labeled oligonucleotides containing amide-linked dinucleoside with pyrene

Reiko Iwase1,2, Yuji Namie1, Tetsuji Yamaoka1 and Akira Murakami1

1 Department of Polymer Science and Engineering, Kyoto Institute of Technology, Matsugasaki, Sakyoku, Kyoto 606-8585, Japan, 2 Department of Biosciences, Teikyo University of Science and Technology, Yatsusawa 2525, Uenohara-machi, Kitatsuru-gun, Yamanashi 409-0193, Japan

Oligonucleotides containing 2'-pyrene modified uridine (Upy) exhibit the increase of the pyrene monomer emission when hybridize with the complementary RNA. In order to examine the effect of restricted C3'-endoconformation of the Upy residue for the enhancement of the pyrene monomer emission, an oligodeoxyribonucleotide containing amide-linked dinucleoside with a pyrene group at the sugar residue (UapyODN) was synthesized by use of 3'-carboxymethyl-5'-O-dimethoxytrityl-2'-O-(1-pyrenylmethyl)-3' -deoxyuridine. NMR analysis indicated that the furanose ring of the uridine derivative was fixed to C3'-endo conformation. The UapyODN showed increase of fluorescence intensity to 7-fold at 375nm when hybridized with complementary oligoribonucleotide. This result suggests that the UapyODN can detect the target RNA.


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