“Inhibition” of the Enzyme Model Tp^Ph,MeZn–OH by Diketo Compounds

Abstract

Abstract In order to gain a structural understanding of zinc enzyme inhibition, the model complex Tp Ph,Me Zn–OH was treated with various diketo compounds. α‐Keto carboxylic acids were attached to the zinc ion as anionic O,O‐chelate ligands, of which benzoylformate was oxidatively decarboxylated in air to form the benzoate complex. Two functionalized β‐diketones did not use their functionality in forming the β‐diketonate complexes. Of the α‐diketones, 2,3‐pentanedione formed the α‐keto enolate complex, while 1‐phenyl‐1,2‐propanedione underwent oxidative C–C coupling resulting in a red dinuclear bis(α‐keto enolato) complex. Of the diaryl‐α‐diketones, benzil did not react, but pyridil underwent hydrolytic cleavage to pyridine‐2‐carbaldehyde and picolinate, of which the latter was bound to the zinc ion as an N,O‐chelate ligand.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)