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Nucleic Acids Symposium Series 2006 50(1):57-58; doi:10.1093/nass/nrl028
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© 2006 Oxford University Press

Synthesis of deoxycytidine derivatives and their use for the selective photo crosslinking with 5-methylcytosine

Haruhiko Taguchi1,3, Akihiro Ohkubo1,3, Kohji Seio2,3 and Mitsuo Sekine1,3

1 Department of Life Science, Tokyo Institute of Technology, Nagatsuta, Midoriku, Yokohama 226-8501, Japan, 2 Frontier Collaborative Research Center, Tokyo Institute of Technology, Nagatsuta, Midoriku, Yokohama 226-8503, Japan, 3 CREST, JST (Japan Science and Technology Agency)

New photoactivatable nucleosides, 4-N-[3-(trifluoromethyl)diazirinyl]benzoyldeoxycytidine derivatives and these corresponding phosphoramidite derivatives were synthesized for the use as photo crosslinking probes. The carbene species was generated by UV irradiation so that it could react with the benzylic C-H of toluene to give a cross-linking product. The diazirine modified DNA 12mer was successfully synthesized by our N-unprotected phosphoramidite method. We studied its hybridization and photo crosslinking abilities. When a 5-methyl deoxycytidine containing complementary DNA oligomer was irradiated in the presence of the DNA 12 mer, crosslinking products were observed.


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