BIOMAT Database Logo BIOMAT Database Logo

Pi-pi stacking assisted binding of aromatic amino acids by copper(II)-aromatic diimine complexes. Effects of ring substituents on ternary complex stability. 2007

Tatsuo Yajima, and Reiko Takamido, and Yuichi Shimazaki, and Akira Odani, and Yasuo Nakabayashi, and Osamu Yamauchi
Unit of Chemistry, Faculty of Engineering, Kansai University, Suita, Osaka 564-8680, Japan.

Ternary Cu(ii) complexes containing an aromatic diimine (DA = di(2-pyridylmethyl)amine (dpa), 4,4'-disubstituted 2,2'-bipyridine (Y(2)bpy; Y = H (bpy), Me, Cl, N(Et)(2), CONH(2) or COOEt) or 2,2'-bipyrimidine) and an aromatic amino acid (AA = l-phenylalanine (Phe), p-substituted phenylalanine (XPhe; X = NH(2), NO(2), F, Cl or Br), l-tyrosine (Tyr), l-tryptophan (Trp) or l-alanine (Ala)) were characterized by X-ray diffraction, spectroscopic and potentiometric measurements. The structures of [Cu(dpa)(Trp)]ClO(4).2H(2)O and [Cu((CONH(2))(2)bpy)(Phe)]ClO(4).H(2)O in the solid state were revealed to have intramolecular pi-pi interactions between the Cu(ii)-coordinated aromatic ring moiety, Cu(DA) (Mpi), and the side chain aromatic ring of the AA (Lpi). The intensities of Mpi-Lpi interactions were evaluated by the stability constants of the ternary Cu(ii) complexes determined at 25 degrees C and I = 0.1 M (KNO(3)), which revealed that the stability enhancement of the Cu(DA)(AA) systems due to the interactions is in the order (CONH(2))(2)bpy < bpy < Me(2)bpy < (Et(2)N)(2)bpy with respect to DA. The results indicate that the electron density of coordinated aromatic diimines influences the intensities of the stacking interactions in the Cu(DA)(AA) systems. The Mpi-Lpi interactions are also influenced by the substituents, X, of Lpi and are in linear relationship with their Hammett sigma(p) values with the exception of X = Cl and Br.

UI MeSH Term Description Entries
D007097 Imines Organic compounds containing a carbon-nitrogen double bond where a NITROGEN atom can be attached to HYDROGEN or an alkyl or aryl group. Imine
D008958 Models, Molecular Models used experimentally or theoretically to study molecular shape, electronic properties, or interactions; includes analogous molecules, computer-generated graphics, and mechanical structures. Molecular Models,Model, Molecular,Molecular Model
D003300 Copper A heavy metal trace element with the atomic symbol Cu, atomic number 29, and atomic weight 63.55. Copper-63,Copper 63
D013056 Spectrophotometry, Ultraviolet Determination of the spectra of ultraviolet absorption by specific molecules in gases or liquids, for example Cl2, SO2, NO2, CS2, ozone, mercury vapor, and various unsaturated compounds. (McGraw-Hill Dictionary of Scientific and Technical Terms, 4th ed) Ultraviolet Spectrophotometry
D014961 X-Ray Diffraction The scattering of x-rays by matter, especially crystals, with accompanying variation in intensity due to interference effects. Analysis of the crystal structure of materials is performed by passing x-rays through them and registering the diffraction image of the rays (CRYSTALLOGRAPHY, X-RAY). (From McGraw-Hill Dictionary of Scientific and Technical Terms, 4th ed) Xray Diffraction,Diffraction, X-Ray,Diffraction, Xray,Diffractions, X-Ray,Diffractions, Xray,X Ray Diffraction,X-Ray Diffractions,Xray Diffractions
D015394 Molecular Structure The location of the atoms, groups or ions relative to one another in a molecule, as well as the number, type and location of covalent bonds. Structure, Molecular,Molecular Structures,Structures, Molecular
D024322 Amino Acids, Aromatic Amino acids containing an aromatic side chain. Aromatic Amino Acids,Amino Acid, Aromatic,Aromatic Amino Acid

Related Publications

Tatsuo Yajima, and Reiko Takamido, and Yuichi Shimazaki, and Akira Odani, and Yasuo Nakabayashi, and Osamu Yamauchi
Nucleobase Stacking Evidenced on Ternary Metal (Palladium(II), Copper(II)) Complexes with Nucleobase Amino Acids and Aromatic Diimines.
February 1999, Inorganic chemistry,
Tatsuo Yajima, and Reiko Takamido, and Yuichi Shimazaki, and Akira Odani, and Yasuo Nakabayashi, and Osamu Yamauchi
Stacking interactions between aromatic amino acids and adenine ring of ATP in zinc mediated ternary complexes.
April 1978, Bioinorganic chemistry,
Tatsuo Yajima, and Reiko Takamido, and Yuichi Shimazaki, and Akira Odani, and Yasuo Nakabayashi, and Osamu Yamauchi
Characterization of an NH-pi interaction in Co(III) ternary complexes with aromatic amino acids.
July 2001, Inorganic chemistry,
Tatsuo Yajima, and Reiko Takamido, and Yuichi Shimazaki, and Akira Odani, and Yasuo Nakabayashi, and Osamu Yamauchi
Hydration of copper(II) amino acids complexes.
May 2018, Journal of computational chemistry,
Tatsuo Yajima, and Reiko Takamido, and Yuichi Shimazaki, and Akira Odani, and Yasuo Nakabayashi, and Osamu Yamauchi
Stability of binary and ternary copper(II) complexes with 1,10-phenanthroline, 2,2'-bipyridyl and some alpha-amino acids in aqueous medium.
July 2009, Chemical & pharmaceutical bulletin,
Tatsuo Yajima, and Reiko Takamido, and Yuichi Shimazaki, and Akira Odani, and Yasuo Nakabayashi, and Osamu Yamauchi
Flavin-Protein Complexes: Aromatic Stacking Assisted by a Hydrogen Bond.
July 2015, Biochemistry,
Tatsuo Yajima, and Reiko Takamido, and Yuichi Shimazaki, and Akira Odani, and Yasuo Nakabayashi, and Osamu Yamauchi
Simple synthesis of ruthenium pi complexes of aromatic amino acids and small peptides.
July 2010, Chemistry (Weinheim an der Bergstrasse, Germany),
Tatsuo Yajima, and Reiko Takamido, and Yuichi Shimazaki, and Akira Odani, and Yasuo Nakabayashi, and Osamu Yamauchi
Ternary complexes of palladium (II) with levamisole and L-amino acids.
January 1999, Journal of inorganic biochemistry,
Tatsuo Yajima, and Reiko Takamido, and Yuichi Shimazaki, and Akira Odani, and Yasuo Nakabayashi, and Osamu Yamauchi
Enhancement of aromatic amino acid-nucleic acid base stacking interaction by metal coordination to base: fluorescence study on a tryptophan-Pt(II)-guanine ternary complex.
August 1995, FEBS letters,
Tatsuo Yajima, and Reiko Takamido, and Yuichi Shimazaki, and Akira Odani, and Yasuo Nakabayashi, and Osamu Yamauchi
Stacking efficiency and flexibility analysis of aromatic amino acids in cap-binding proteins.
June 2008, Proteins,
Copied contents to your clipboard!