Properties of the indole ring in metal complexes. A comparison with the phenol ring

J Inorg Biochem. 2015 Jul:148:105-15. doi: 10.1016/j.jinorgbio.2015.03.001. Epub 2015 Mar 11.

Abstract

Tryptophan (Trp), an essential amino acid, has an indole ring with a high electron density and is frequently seen at the proximal position of the metal site in metalloproteins. For example, the indole ring of Trp has been reported to interact weakly with Cu(I) in a Cu chaperone CusF. Another aromatic amino acid, tyrosine (Tyr), has a phenol ring, which is an important metal binding site in various metalloproteins. Although the structures of the aromatic rings are different, they both have a weakly acidic moiety and perform some similar roles in biological systems, such as radical formation and electron transfer. In this review, we focus on these and other properties of the indole and phenol rings in metal-containing systems.

Keywords: Metal complexes; Radical formation; Tryptophan; Tyrosine; σ- and π-bondings.

Publication types

  • Comparative Study
  • Research Support, Non-U.S. Gov't
  • Review

MeSH terms

  • Binding Sites
  • Coordination Complexes / chemistry*
  • Indoles / chemistry*
  • Metalloproteins / chemistry
  • Metals / chemistry*
  • Models, Chemical
  • Molecular Structure
  • Phenol / chemistry*
  • Tryptophan / chemistry
  • Tyrosine / chemistry

Substances

  • Coordination Complexes
  • Indoles
  • Metalloproteins
  • Metals
  • Phenol
  • Tyrosine
  • indole
  • Tryptophan