Copper catalyzed oxidation of amino acids

Szabina Góger, J. Pap, Dóra Bogáth, A. Jalila Simaan, G. Speier, Michel Giorgi, J. Kaizer

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

Copper(II) chloride and novel bis(1-amino(cyclo)alkane-1-carboxylato- κ2N,O)copper(II) complexes as catalysts were studied in relation with enzymatic oxidation of amino acids. The oxidation of aminophosphonate derivative: (1-amino-1-methyl)ethylphosphonic acid was also investigated. Two bis(1-aminocycloalkane-1-carboxylato-κ2N,O) copper(II) complexes were structurally characterized. Surprisingly, while the 1-aminocyclobutane-1-carboxylate complex has square planar (SP-4) copper(II) center with trans-orientated ligands, the 1-aminocyclohexane-1-carboxylate complex has μ-carboxylato dimeric structure with square pyramidal (SPY-5) sites, one with cis- and one with trans-orientated ligands. Redox behavior of the bis(1-amino(cyclo)alkane-1-carboxylato-κ2N,O)copper(II) complexes was also investigated. Catalytic oxidations were carried out in alkaline DMF-water mixtures using H2O2 as oxidant and the complexes as catalysts. The observed potentials for the irreversible current peaks associated with the Cu(II) to Cu(I) reduction and the rates of the amino acid oxidations show inverse trend. This suggests that the Cu(II)/Cu(I) redox cycling due to the presence of H2O2 plays important role in the peroxide/copper activation that in turn provides the observed products.

Original languageEnglish
Pages (from-to)37-44
Number of pages8
JournalPolyhedron
Volume73
DOIs
Publication statusPublished - May 8 2014

Fingerprint

amino acids
Amino acids
Copper
Amino Acids
copper
Oxidation
oxidation
Alkanes
Paraffins
carboxylates
alkanes
Ligands
Catalysts
Catalytic oxidation
Peroxides
catalysts
ligands
Oxidants
peroxides
Chemical activation

Keywords

  • Amino acids
  • Biomimetic oxidation
  • Copper(II)
  • Kinetic studies
  • Oxidase activity

ASJC Scopus subject areas

  • Inorganic Chemistry
  • Materials Chemistry
  • Physical and Theoretical Chemistry

Cite this

Copper catalyzed oxidation of amino acids. / Góger, Szabina; Pap, J.; Bogáth, Dóra; Simaan, A. Jalila; Speier, G.; Giorgi, Michel; Kaizer, J.

In: Polyhedron, Vol. 73, 08.05.2014, p. 37-44.

Research output: Contribution to journalArticle

Góger, Szabina ; Pap, J. ; Bogáth, Dóra ; Simaan, A. Jalila ; Speier, G. ; Giorgi, Michel ; Kaizer, J. / Copper catalyzed oxidation of amino acids. In: Polyhedron. 2014 ; Vol. 73. pp. 37-44.
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