Singlet oxygen (1O2) can be easily generated by a sensitizer, solar radiation and molecular oxygen. 1O2 is important in a wide variety of biological and environmental systems. The products, mechanisms, and kinetics of the 1O2 reactions are well studied in organic solvents. However, very limited research has been reported on 1O2 chemistry in aqueous media. The main goal of the present work is to study the 1O2 reactions with Domoic Acid (DA) in aqueous solutions. Domoic Acid (DA) is a natural toxin produced during the harmful algal bloom of the diatom Pseudonitzchia. DA contaminated water and food have severe impacts on human health, wildlife and the environment. DA contains an electron rich trisubstituted Z, E diene functionality which has a critical role in the toxicity of the molecule and is very appealing for 1O2 attack. Herein, we report the major products of these reactions identified NMR and LC-UV-HRMS and the mechanistic implications of the product distribution. In addition, the kinetics of the reaction and the biological activity of the product mixtures are described. The reactions of 1O2 with DA likely represent an important pathway for the photochemical transformation of DA in the environment and could provide an alternative detoxification strategy for DA contaminated water and/or food.

Studies of the singlet oxygenation of Domoic acid: Mechanisms, kinetics and biological significance.

2019 Spring National Meeting

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