Proton, copper(II) and nickel(II) complexes of some amadori rearrangement products of D-glucose and amino acids

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Abstract

The formation of the copper(II) and nickel(II) complexes of six Amadori rearrangement products of D-glucose with amino acids ('fructose-amino acids') was investigated by potentiometry, CD and EPR spectroscopy. The -I effect of the fructose residue in the ligands was reflected by the protonation constants of their amino groups. In the complexes ML formed with the copper(II) ion, besides the amino acid-type coordination a weak interaction with non-deprotonated alcoholic hydroxy groups was demonstrated by CD studies. Increase of the pH may lead to transformation of the species ML to give complexes ML2 and/or MLH-1. The former contains two nitrogen donor atoms in the copper(II) coordination sphere, while in MLH-1 the ligands are coordinated through their carboxyl, amino and deprotonated alcoholic OH groups, as revealed by equilibrium, CD and EPR studies. Above pH ∼7, a redox reaction takes place between copper(II) and the ligand. The nickel(II) ion forms amino acid- type parent complexes ML and ML2, while deprotonated species predominate in solution above pH ∼9.

Original languageEnglish
Pages (from-to)57-66
Number of pages10
JournalInorganica Chimica Acta
Volume214
Issue number1-2
DOIs
Publication statusPublished - 1993

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Nickel
glucose
Glucose
amino acids
Protons
Amino acids
Copper
nickel
Amino Acids
copper
Fructose
acids
protons
Ligands
products
ligands
Paramagnetic resonance
Potentiometry
Ions
potentiometric analysis

ASJC Scopus subject areas

  • Biochemistry
  • Inorganic Chemistry
  • Physical and Theoretical Chemistry
  • Materials Chemistry

Cite this

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title = "Proton, copper(II) and nickel(II) complexes of some amadori rearrangement products of D-glucose and amino acids",
abstract = "The formation of the copper(II) and nickel(II) complexes of six Amadori rearrangement products of D-glucose with amino acids ('fructose-amino acids') was investigated by potentiometry, CD and EPR spectroscopy. The -I effect of the fructose residue in the ligands was reflected by the protonation constants of their amino groups. In the complexes ML formed with the copper(II) ion, besides the amino acid-type coordination a weak interaction with non-deprotonated alcoholic hydroxy groups was demonstrated by CD studies. Increase of the pH may lead to transformation of the species ML to give complexes ML2 and/or MLH-1. The former contains two nitrogen donor atoms in the copper(II) coordination sphere, while in MLH-1 the ligands are coordinated through their carboxyl, amino and deprotonated alcoholic OH groups, as revealed by equilibrium, CD and EPR studies. Above pH ∼7, a redox reaction takes place between copper(II) and the ligand. The nickel(II) ion forms amino acid- type parent complexes ML and ML2, while deprotonated species predominate in solution above pH ∼9.",
author = "B. Gyurcsik and T. Gajda and L. Nagyb and K. Burger and A. Rockenbauer and L. Korecz",
year = "1993",
doi = "10.1016/S0020-1693(00)87526-X",
language = "English",
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TY - JOUR

T1 - Proton, copper(II) and nickel(II) complexes of some amadori rearrangement products of D-glucose and amino acids

AU - Gyurcsik, B.

AU - Gajda, T.

AU - Nagyb, L.

AU - Burger, K.

AU - Rockenbauer, A.

AU - Korecz, L.

PY - 1993

Y1 - 1993

N2 - The formation of the copper(II) and nickel(II) complexes of six Amadori rearrangement products of D-glucose with amino acids ('fructose-amino acids') was investigated by potentiometry, CD and EPR spectroscopy. The -I effect of the fructose residue in the ligands was reflected by the protonation constants of their amino groups. In the complexes ML formed with the copper(II) ion, besides the amino acid-type coordination a weak interaction with non-deprotonated alcoholic hydroxy groups was demonstrated by CD studies. Increase of the pH may lead to transformation of the species ML to give complexes ML2 and/or MLH-1. The former contains two nitrogen donor atoms in the copper(II) coordination sphere, while in MLH-1 the ligands are coordinated through their carboxyl, amino and deprotonated alcoholic OH groups, as revealed by equilibrium, CD and EPR studies. Above pH ∼7, a redox reaction takes place between copper(II) and the ligand. The nickel(II) ion forms amino acid- type parent complexes ML and ML2, while deprotonated species predominate in solution above pH ∼9.

AB - The formation of the copper(II) and nickel(II) complexes of six Amadori rearrangement products of D-glucose with amino acids ('fructose-amino acids') was investigated by potentiometry, CD and EPR spectroscopy. The -I effect of the fructose residue in the ligands was reflected by the protonation constants of their amino groups. In the complexes ML formed with the copper(II) ion, besides the amino acid-type coordination a weak interaction with non-deprotonated alcoholic hydroxy groups was demonstrated by CD studies. Increase of the pH may lead to transformation of the species ML to give complexes ML2 and/or MLH-1. The former contains two nitrogen donor atoms in the copper(II) coordination sphere, while in MLH-1 the ligands are coordinated through their carboxyl, amino and deprotonated alcoholic OH groups, as revealed by equilibrium, CD and EPR studies. Above pH ∼7, a redox reaction takes place between copper(II) and the ligand. The nickel(II) ion forms amino acid- type parent complexes ML and ML2, while deprotonated species predominate in solution above pH ∼9.

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