Atrazine is one of the most prolific herbicides used in the United States and Australia. It has been shown to negatively affect sexual development in frog populations due to its estrogen mimicking effect. Atrazine is recalcitrant to environmental degradation due to the presence of a C-Cl bond. However, a bacterial enzymatic remediation pathway has evolved since atrazine’s introduction to the environment. The first step of the enzymatic pathway utilizes atrazine chlorohydrolase (AtzA), found in Pseudomonas aeruginosa, to cleave the C-Cl bond in atrazine. AtzA employs iron(II) in the active site to facilitate the hydrolysis of atrazine with specificity for halogenated substrates. In this study, a trispyrazolylborate (Tp) ligand was synthesized and complexed with iron to form a small molecule mimic of the AtzA active site. The Tp-Fe complex was reacted with halogenated pyridines, which are structurally analogous to atrazine. These complexes were characterized via NMR spectroscopy to provide insight into substrate binding orientation in the enzymatic system and the role of the metal center.

Investigation of substrate specificity of atrazine chlorohydrolase (AtzA) using trispyrazolylborate (Tp) iron halogenated pyridine complexes

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.