Simple synthesis of ruthenium pi complexes of aromatic amino acids and small peptides.
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.
Perekalin
Dmitry S
DS
A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 119991 Moscow, Russian Federation.
Karslyan
Eduard E
EE
Petrovskii
Pavel V
PV
Nelyubina
Yulia V
YV
Lyssenko
Konstantin A
KA
Kononikhin
Alexey S
AS
Nikolaev
Eugene N
EN
Kudinov
Alexander R
AR
D024322:Amino Acids, Aromatic / Q000138:chemical synthesis* / Q000737:chemistry*; D008027:Light; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry*; D012428:Ruthenium / Q000737:chemistry*; D013237:Stereoisomerism
D024322:Amino Acids, Aromatic; D009942:Organometallic Compounds; D010455:Peptides; D012428:Ruthenium