Simple Synthesis of Ruthenium π Complexes of Aromatic Amino Acids and Small Peptides

• Published in: Chemistry : a European journal Vol. 16; no. 28; pp. 8466 - 8470
• Main Authors: Perekalin, Dmitry S., Karslyan, Eduard E., Petrovskii, Pavel V., Nelyubina, Yulia V., Lyssenko, Konstantin A., Kononikhin, Alexey S., Nikolaev, Eugene N., Kudinov, Alexander R.
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 26.07.2010; WILEY‐VCH Verlag
• Subjects: amino acids; Amino Acids, Aromatic - chemical synthesis; Amino Acids, Aromatic - chemistry; bioorganometallic chemistry; compound labeling; Light; Magnetic Resonance Spectroscopy; Molecular Structure; Organometallic Compounds - chemical synthesis; Organometallic Compounds - chemistry; Peptides - chemical synthesis; Peptides - chemistry; ruthenium; Ruthenium - chemistry; sandwich complexes; Stereoisomerism
• ISSN: 0947-6539; 1521-3765
• DOI: 10.1002/chem.201000520

The interaction of [Ru(η6‐C10H8)(Cp)]+ (Cp=C5H5) 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(η6‐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(η6‐C10H8)(Cp)]+ was also used for selective labeling of Tyr and Phe residues of small peptides, namely, angiotensin I and II derivatives. Simple labeling of amino acids and peptides: Ruthenium π complexes with aromatic amino acids and small peptides have been synthesized in water at room temperature (see scheme) in the presence of oxygen and concomitant biological substances (non‐aromatic amino acids, sugars, and nucleotides).