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Communication | Special issue | Vol 70, No. 1, 2006, pp.147-152
Published online, 24th October, 2006
DOI: 10.3987/COM-06-S(W)46
Cytochrome c Oxidase Active Site Mimics: New Ligands for Copper and an Unexpected Oxidative C-C Bond Formation

Yakira R. Landaverry, Kimberly N. White, Marilyn M. Olmstead, Ólöf Einarsdóttir, and Joseph P. Konopelski*

*Department of Chemistry, University of California, Santa Cruz, CA 95064, U.S.A.

Abstract

Ligands that mimic the unusual active site polypeptide of cytochrome c oxidase have been prepared in overall good yield; structures of the corresponding Cu(II) complexes are secured by single crystal x-ray analysis. The key step in the synthesis of the ligands is the coupling of a suitable organolead(IV) phenol derivative with the ε-N of the histidine imidazole ring. In the process of preparing crystals of a tridentate ester ligand an unusual oxidative C-C bond-forming reaction occurs that affords the imidazotetrahydropyridine ring system.