Photoaddition of 5-bromouracil to uracil in oligonucleotides leading to 5,5'-bipyrimidine-type adducts: mechanism of the photoreaction.

Jolanta Lepczyńska, Krzysztof Komodziński, Jan Milecki, Ryszard Kierzek, Zofia Gdaniec, Stefan Franzen, Bohdan Skalski

Faculty of Chemistry, Adam Mickiewicz University, Grunwaldzka 6, 60-780 Poznań, Poland.

The Journal of organic chemistry 2012 Dec 21

filter terms:

5-Bromouracil ((Br)U) modified di- and hexanucleotides having (Br)U flanked on the 5' or the 3' side by uracil (U) have been synthesized, and their photochemical reactivity was examined under the conditions of irradiation with near UV light. The results indicate that the primary photochemical process in all of these compounds involves the formation of an intermediate cyclobutane phodoadduct composed of (Br)U and U, which undergoes further photochemically and thermally induced transformations to 5,5'-bipyrimidine type adducts.

Citation

Jolanta Lepczyńska, Krzysztof Komodziński, Jan Milecki, Ryszard Kierzek, Zofia Gdaniec, Stefan Franzen, Bohdan Skalski. Photoaddition of 5-bromouracil to uracil in oligonucleotides leading to 5,5'-bipyrimidine-type adducts: mechanism of the photoreaction. The Journal of organic chemistry. 2012 Dec 21;77(24):11362-7