Synthesis of fluorescent cyclic cytosine nucleosides and their fluorescent properties upon incorporation into oligonucleotides

Synthesis of fluorescent cyclic cytosine nucleosides and their fluorescent properties upon incorporation into oligonucleotides
2006
Masahiro Mizuta3, Kenichi Miyata1,3, Kohji Seio2,3, Tomofumi Santa4 and Mitsuo Sekine1,3
1 Department of Life Science, Tokyo Institute of Technology, Nagatsuta, Midoriku, Yokohama 226-8501, Japan, 2 Division of Collaborative Research for Bioscience and Biotechnology, Frontier Collaborative Research Center, Tokyo Institute of Technology, Nagatsuta, Midoriku, Yokohama 226-8503, Japan, 3 CREST, JST (Japan Science and Technology Agency), The University of Tokyo, Bunkyo-ku, Tokyo, Japan, 4 Graduate School of Pharmaceutical Sciences, The University of Tokyo, Bunkyo-ku, Tokyo, Japan
Nucleic Acids Symposium Series 2006
We report here the synthesis and spectroscopic characterization of a new fluorescent pyrimidopyrimidoindole nucleoside derivative (dCPPI) modified at the cytosine base. The photophysical properties of dCPPI were examined by fluorescent spectroscopy and quantum chemical calculations. It was found that dCPPI-labeled oligonucleotides gave almost the same thermal stability as that of the corresponding unmodified sequences. In addition, the quantum yield of dCPPI in the double-stranded state was significantly higher than that in the single-stranded state.
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