Synthesis of a Cyclic Pentapeptide Mimic of the Active Site His-Tyr Cofactor of Cytochrome c Oxidase

Synthesis of a Cyclic Pentapeptide Mimic of the Active Site His-Tyr Cofactor of Cytochrome c Oxidase

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 p...

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Veröffentlicht in:Journal of organic chemistry 2009-11, Vol.74 (21), p.8212-8218
Hauptverfasser: Mahoney, Maximillian E, Oliver, Allen, Einarsdóttir, Ólöf, Konopelski, Joseph P
Format: Artikel
Sprache:eng
Schlagworte:
Catalytic Domain
Chemistry
Crystallography, X-Ray
Electron Transport Complex IV - chemistry
Electron Transport Complex IV - metabolism
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Histidine - chemistry
Lysine - chemistry
Magnetic Resonance Spectroscopy
Mass Spectrometry
Models, Molecular
Molecular Mimicry
Oligopeptides - chemical synthesis
Oligopeptides - chemistry
Organic chemistry
Peptides
Preparations and properties
Protein Conformation
Spectrophotometry, Infrared
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Zusammenfassung: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo901744y