Jaden Webb
Computational Modelling of Nature’s First Step in Rotenone Biosynthesis: Understanding How L-Phenylalanine is Transformed into trans-Cinnamic Acid
Home Institution: Missouri State University
Advisor: Matthew R. Siebert
Abstract
Nature provides many lessons on the biological impacts of chemical agents. Rotenone, a naturally occurring substance in the rotenoid family, was once used as a pesticide and piscicide. Its use was banned in the US due to an alarming realization: geographical areas where rotenone was used showed an increased rate of Parkinson’s disease. The cause of Parkinson’s is not yet understood but understanding how Nature produces rotenone may help lead us toward an answer. Rotenone is naturally synthesized (called biosynthesis) in plants from the amino acid L-phenylalanine. There is some controversy as to whether this first step (conversion of L-phenylalanine to trans-cinnamic acid) proceeds via an E1cb, E1, or E2 elimination pathway. We (among others) hypothesize that L-phenylalanine is converted to trans-cinnamic acid through an E1cb elimination reaction.