Soluble methane monooxygenase (sMMO) from methanotrophic bacteria is capable of oxidizing C–H to C–OH bonds using O2. This enzyme is of potential technological significance for diverse applications, including the functionalization of petrochemical hydrocarbons and bioremediation of oil spills. Our laboratory previously developed a phenol-imine macrocyclic ligand framework, (H2PIM), which mimics the structural arrangement of the sMMOH active site with the addition of two bulky external carboxylate ligands. We have now designed and synthesized a phenol-imine macrocyclic ligand functionalized with an internal, dangling carboxylate (H3PIMIC). The covalently tethered small carboxylic acid side chain provides not only sufficient preorganization, but also conformational flexibility, allowing for the entry of guest molecules to the diiron center. The activation of C–H bonds with these diiron complexes will be discussed. This work was supported by a grant from the National Institute of General Medical Sciences.

Synthetic modeling of the sMMO diiron active site with a preorganized macrocyclic ligand framework

250th National Meeting (2015)

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