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

Abstract

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.