Synthesis of tridentate ligands based on theroretical design to mimic HPCD enzyme

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2018

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Gökçe, Muzaffer

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There is an increasing interest on the aromatic oxidative ring opening reactions due to their challenging features. Among these reactions, the ones using molecular oxygen attract even more attention. In one of these aromatic ring opening reactions, homoprotocatechuate dioxygenase (HPCD) enzyme is used as a catalyst. The active site of this enzyme consists of either iron or manganese ions. In this work, two tridentate ligands have been designed theoretically in order to mimic the active site of this enzyme to perform the same reaction using smaller organic molecules instead of enzyme. These ligands are composed of adenine, imidazole and carboxylic acid moieties. Based on calculations, -NH2 group on adenine would be acting as a base which is involved in the hydrogen transfer from –OH group of catechol to dioxygen on the metal center. This transfer is found to be lowering the activation barrier of one intermediate. These designed ligands are attempted to be synthesized using different strategies. Tremendous efforts have been spent however, the synthesis of these designed ligands could not be succeeded so far. There is still ongoing work to complete the synthesis of these ligands.

Subject Keywords

Enzymes., Ligands., Adenine., Imidazoles., Molecular structure., Chemistry

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http://etd.lib.metu.edu.tr/upload/12621785/index.pdf
https://hdl.handle.net/11511/27026

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Graduate School of Natural and Applied Sciences, Thesis

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Citation Formats

M. Gökçe, “Synthesis of tridentate ligands based on theroretical design to mimic HPCD enzyme,” M.S. - Master of Science, Middle East Technical University, 2018.