Simple synthesis of ruthenium pi complexes of aromatic amino acids and small peptides

Chemistry. 2010 Jul 26;16(28):8466-70. doi: 10.1002/chem.201000520.

Abstract

The interaction of [Ru(eta(6)-C(10)H(8))(Cp)](+) (Cp=C(5)H(5)) with aromatic amino acids (L-phenylalanine, L-tyrosine, L-tryptophane, D-phenylglycine, and L-threo-3-phenylserine) under visible-light irradiation gives the corresponding [Ru(eta(6)-amino acid)(Cp)](+) complexes in near-quantitative yield. The reaction proceeds in air at room temperature in water and tolerates the presence of non-aromatic amino acids (except those which are sulfur containing), monosaccharides, and nucleotides. The complex [Ru(eta(6)-C(10)H(8))(Cp)](+) was also used for selective labeling of Tyr and Phe residues of small peptides, namely, angiotensin I and II derivatives.

MeSH terms

  • Amino Acids, Aromatic / chemical synthesis*
  • Amino Acids, Aromatic / chemistry*
  • Light
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Organometallic Compounds / chemical synthesis*
  • Organometallic Compounds / chemistry*
  • Peptides / chemical synthesis*
  • Peptides / chemistry*
  • Ruthenium / chemistry*
  • Stereoisomerism

Substances

  • Amino Acids, Aromatic
  • Organometallic Compounds
  • Peptides
  • Ruthenium