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

Org Lett. 2000 Oct 5;2(20):3055-7. doi: 10.1021/ol006271w.

Abstract

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.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Binding Sites
  • Catalysis
  • Copper
  • Dipeptides / chemical synthesis*
  • Dipeptides / chemistry
  • Electron Transport Complex IV / chemistry*
  • Histidine / chemistry
  • Imidazoles / chemical synthesis*
  • Imidazoles / chemistry
  • Indicators and Reagents
  • Tyrosine / chemistry

Substances

  • Dipeptides
  • Imidazoles
  • Indicators and Reagents
  • Tyrosine
  • Histidine
  • Copper
  • Electron Transport Complex IV