title: Phenylalanine--a biogenic ligand with flexible η6- and η6:κ1-coordination at ruthenium(II) centres.
abstract: The reaction of (S)-2,5-dihydrophenylalanine 1 with ruthenium(III) chloride yields the μ-chloro-bridged dimeric η(6)-phenylalanine ethyl ester complex 3, which can be converted into the monomeric analogue, η(6):κ(1)-phenylalanine ethyl ester complex 12, under basic conditions. Studies were carried out to determine the stability and reactivity of complexes bearing η(6)- and η(6):κ(1)-chelating phenylalanine ligands under various conditions. Reaction of 3 with ethylenediamine derivatives N-p-tosylethylenediamine or 1,4-di-N-p-tosylethylenediamine results in the formation of monomeric η(6):κ(1)-phenylalanine ethyl ester complexes 14 and 15, which could be saponified yielding complexes 16 and 17 without changing the inner coordination sphere of the metal centre. The structure of η(6):κ(1)-phenylalanine complex 17 and an N-κ(1)-phenylalanine complex 13 resulting from the reaction of 3 with an excess of pyridine were confirmed by X-ray crystallography.
authors: Technische Universität München, Department Chemie, Lichtenbergstr. 4, D-85747 Garching, Germany.
authors: Thomas
authors: T
authors: Reiner
authors: Dominik
authors: D
authors: Jantke
authors: Xiao-He
authors: XH
authors: Miao
authors: Alexander N
authors: AN
authors: Marziale
authors: Florian J
authors: FJ
authors: Kiefer
authors: Jörg
authors: J
authors: Eppinger
mesh_terms: D002621:Chemistry / Q000379:methods; D002626:Chemistry, Pharmaceutical / Q000379:methods; D002712:Chlorides / Q000737:chemistry; D018360:Crystallography, X-Ray / Q000379:methods; D053138:Cyclohexenes / Q000737:chemistry*; D004121:Dimethyl Sulfoxide / Q000737:chemistry; D015195:Drug Design; D004952:Esters; D008024:Ligands; D009682:Magnetic Resonance Spectroscopy / Q000379:methods; D008670:Metals / Q000737:chemistry; D008968:Molecular Conformation; D010649:Phenylalanine / Q000031:analogs & derivatives* / Q000737:chemistry*; D012428:Ruthenium / Q000737:chemistry*; D012997:Solvents / Q000737:chemistry
chemical_list: D002712:Chlorides; D053138:Cyclohexenes; D004952:Esters; D008024:Ligands; D008670:Metals; D012997:Solvents; C004174:2,5-dihydrophenylalanine; D010649:Phenylalanine; D012428:Ruthenium; D004121:Dimethyl Sulfoxide