title: Synthesis of a cyclic pentapeptide mimic of the active site His-Tyr cofactor of cytochrome c oxidase.
abstract: Arylboronic acid based technology provides a mild, regioselective, and nontoxic N-arylation procedure for accessing the unusual N-arylated side chain histidine found in the active site of cytochrome c oxidase (CcO). The N-arylated histidine is elaborated to the complete cytochrome c oxidase cyclic pentapeptide cofactor. Molecular modeling of the cofactor provides insight into the dynamic character of the N-aryl bond.
authors.affiliation: Department of Chemistry and Biochemistry, University of California, Santa Cruz, California 95064, USA.
authors.forename: Maximillian E
authors.initials: ME
authors.lastname: Mahoney
authors.forename: Allen
authors.initials: A
authors.lastname: Oliver
authors.forename: Olöf
authors.initials: O
authors.lastname: Einarsdóttir
authors.forename: Joseph P
authors.initials: JP
authors.lastname: Konopelski
mesh_terms: D020134:Catalytic Domain; D018360:Crystallography, X-Ray; D003576:Electron Transport Complex IV / Q000737:chemistry / Q000378:metabolism*; D006639:Histidine / Q000737:chemistry*; D008239:Lysine / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008958:Models, Molecular; D018716:Molecular Mimicry; D009842:Oligopeptides / Q000138:chemical synthesis* / Q000737:chemistry; D011487:Protein Conformation; D013055:Spectrophotometry, Infrared
chemical_list: D009842:Oligopeptides; D006639:Histidine; D003576:Electron Transport Complex IV; D008239:Lysine