Free radicals are key intermediates in the damage of biological molecules such as proteins. These altered proteins can then damage DNA molecules, which can cause mutations and possibly cancer. Mutated DNA can also lead to cell death, which can ironically be beneficial to a cancer patient by targeting his or her tumor cells. In our research, we are synthesizing a-amino acid derivatives that include a carbon-selenium bond. This bond can be homolytically cleaved by ultra violet (UV) light to produce specific amino acid radicals. Because proteins are merely a combination of many amino acids, a single amino acid radical can serve as a model for the larger, damaged biomolecule. Work is currently underway toward the synthesis of selenium-containing derivatives of the amino acids phenylalanine and valine. These compounds are being prepared from reductive amination of the corresponding selenium-containing a-oxoesters.

Synthesis of phenylalanine and valine radical precursors

245th National Meeting (2013)

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