Summer is a chemistry graduate student in the Narayan lab at the University of Michigan. Her research is focused on identifying enzymes from secondary metabolite pathways with potential synthetic utility and developing methods based on these biocatalysts to enable access to biologically active target molecules. She received a B. A. in Chemistry from Bryn Mawr College in 2015, where she worked on development of new palladium-catalyzed cross-coupling methodology.
Enzymatic Oxidative Dearomatization
Oxidative dearomatization allows for rapid increase in molecular complexity from arenes to highly-functionalized chiral products. Typical chemical methods require toxic or hazardous oxidizing reagents and few asymmetric methods are available. In nature, these transformations can be mediated by flavin monooxygenases (FMOs), which use one atom from dioxygen to oxidize densely functionalized aromatic substrates with exquisite site and stereospecificity. Our goal is to generate FMOs to enable the chemoenzymatic synthesis of complex molecules. Our initial studies have identified several wild type FMOs which demonstrate substrate flexibility, excellent catalytic activity and the potential for scalability in the oxidative dearomatization of densely functionalized phenols. Currently we are generating a library of FMO mutants using directed evolution techniques to test for improved substrate scope and activity. In our efforts to improve the scalability of this biotransformation we have employed a cofactor recycling system and used whole cell catalysis to isolate synthetically useful quantities of the dearomatized products.