Stereoselectivity in the [2+2] photodimerization of derivatives of orotic acid

ORGN 265

Juliet M. Hahn1, Brandi Greene2, Karen Brawner2, and Madhvi Patel2. (1) Department of Chemistry and Biochemistry, University of Oklahoma, 620 Parrington Oval, Norman, OK 73019, (2) Department of Chemistry and Physics, Arkansas State University, P.O. Box 419, State University, AR 72467
The [2+2] photodimerization of orotic acid, a derivative of thymine, is used to simulate the primary mode of DNA damage believed to cause sunlight induced cancer. The unmodified orotic acid as well as various esterified derivatives is used to investigate stereoselectivity in the photodimerizaton as well as to study the efficiency of the photodimerization reaction. Various orotic acid esters were synthesized and investigated.