Synthesis and Properties of 2'-Deoxyuridine Analogues Bearing Various Azobenzene Derivatives at the C5 Position

Shohei Mori, Kunihiko Morihiro, Yuuya Kasahara, Shin-ichi Tsunoda, Satoshi Obika
2015 Chemosensors  
Nucleic acids that change their properties upon photo-irradiation could be powerful materials for molecular sensing with high spatiotemporal resolution. Recently, we reported a photo-isomeric nucleoside bearing azobenzene at the C5 position of 2'-deoxyuridine (dU Az ), whose hybridization ability could be reversibly controlled by the appropriate wavelength of light. In this paper, we synthesized and evaluated dU Az analogues that have various para-substitutions on the azobenzene moiety.
more » ... ene moiety. Spectroscopic measurements and HPLC analyses revealed that the para-substitutions of the azobenzene moiety strongly affect the photo-isomerization ability and thermal stability of the cis-form. The results suggest that proper substitution of the azobenzene moiety can improve the properties of dU Az as a light-responsive nucleic acid probe.
doi:10.3390/chemosensors3020036 fatcat:zyn34jnyxnbkljuxk6usokori4