Synthesis and properties of fluorescent-labeled oligonucleotides containing amide-linked dinucleoside with pyrene.
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 375 nm when hybridized with complementary oligoribonucleotide. This result suggests that the UapyODN can detect the target RNA.
Iwase
Reiko
R
Department of Polymer Science and Engineering, Kyoto Institute of Technology, Matsugasaki, Sakyoku, Kyoto 606-8585, Japan.
Namie
Yuji
Y
Yamaoka
Tetsuji
T
Murakami
Akira
A
D000577:Amides / Q000737:chemistry*; D015226:Dinucleoside Phosphates / Q000737:chemistry*; D005456:Fluorescent Dyes / Q000737:chemistry*; D009841:Oligonucleotides / Q000138:chemical synthesis* / Q000737:chemistry*; D011721:Pyrenes / Q000138:chemical synthesis / Q000737:chemistry*; D014529:Uridine / Q000138:chemical synthesis / Q000737:chemistry
D000577:Amides; D015226:Dinucleoside Phosphates; D005456:Fluorescent Dyes; D009841:Oligonucleotides; D011721:Pyrenes; C030984:pyrene; D014529:Uridine