ol060659v_si_001.pdf (435.31 kB)
Facile Photocyclization Chemistry of 5-Phenylthio-2‘-deoxyuridine in Duplex DNA
journal contribution
posted on 2006-06-08, 00:00 authored by Yu Zeng, Huachuan Cao, Yinsheng WangWe report here the synthesis of 5-phenylthio-2‘-deoxyuridine (dPhSU), its incorporation into oligodeoxynucleotides (ODNs), and its photocyclization
chemistry. Irradiation of dinucleoside monophosphate d(PhSUG) and dPhSU-bearing duplex ODNs with 254 nm light results in the facile formation
of a cyclic product where the C6 of uracil is covalently bonded to the C2 of the phenyl ring. The chemistry reported here may serve as the
basis for the efficient preparation of a new class of duplex DNA with an extended π system.