Complete N-1 regiocontrol in the formation of N-arylimidazoles. Synthesis of the active site His-Tyr side chain coupled dipeptide of cytochrome c oxidase.
Under catalysis by copper(II) acetate, complete regiocontrol (N-1 versus N-3) was obtained in the arylation of substituted imidazoles with aryllead(IV) reagents. The mildness of the reaction conditions (rt, no added base) allows for the first synthesis of the histidine-tyrosine side chain coupled dipeptide found in the active site of cytochrome c oxidase.
Elliott
G I
GI
Department of Chemistry and Biochemistry, University of California, Santa Cruz, California 95064, USA.
Konopelski
J P
JP
D001665:Binding Sites; D002384:Catalysis; D003300:Copper; D004151:Dipeptides / Q000138:chemical synthesis* / Q000737:chemistry; D003576:Electron Transport Complex IV / Q000737:chemistry*; D006639:Histidine / Q000737:chemistry; D007093:Imidazoles / Q000138:chemical synthesis* / Q000737:chemistry; D007202:Indicators and Reagents; D014443:Tyrosine / Q000737:chemistry
D004151:Dipeptides; D007093:Imidazoles; D007202:Indicators and Reagents; D014443:Tyrosine; D006639:Histidine; D003300:Copper; D003576:Electron Transport Complex IV