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Simple Synthesis of Ruthenium π Complexes of Aromatic Amino Acids and Small Peptides
Author(s) -
Perekalin Dmitry S.,
Karslyan Eduard E.,
Petrovskii Pavel V.,
Nelyubina Yulia V.,
Lyssenko Konstantin A.,
Koikhin Alexey S.,
Nikolaev Eugene N.,
Kudinov Alexander R.
Publication year - 2010
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201000520
Subject(s) - chemistry , amino acid , phenylalanine , aromatic amino acids , yield (engineering) , ruthenium , tyrosine , monosaccharide , peptide , stereochemistry , organic chemistry , catalysis , biochemistry , materials science , metallurgy
The interaction of [Ru(η 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(η 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(η 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.