Synthesis of deoxycytidine derivatives and their use for the selective photo crosslinking with 5-methylcytosine.
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.
Taguchi
Haruhiko
H
Department of Life Science, Tokyo Institute of Technology, Nagatsuta, Midoriku, Yokohama 226-8501, Japan.
Ohkubo
Akihiro
A
Seio
Kohji
K
Sekine
Mitsuo
M
D044503:5-Methylcytosine / Q000737:chemistry*; D003432:Cross-Linking Reagents / Q000138:chemical synthesis / Q000737:chemistry*; D003562:Cytidine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D003978:Diazomethane / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D009838:Oligodeoxyribonucleotides / Q000138:chemical synthesis / Q000737:chemistry / Q000528:radiation effects; D009943:Organophosphorus Compounds / Q000737:chemistry; D014466:Ultraviolet Rays
D003432:Cross-Linking Reagents; D009838:Oligodeoxyribonucleotides; D009943:Organophosphorus Compounds; C434331:phosphoramidite; D003562:Cytidine; D003978:Diazomethane; D044503:5-Methylcytosine