Bio-inspired amino acid oxidation by a non-heme iron catalyst

Szabina Góger, Dóra Bogáth, Gábor Baráth, A. Jalila Simaan, G. Speier, J. Kaizer

Research output: Contribution to journalArticle

12 Citations (Scopus)

Abstract

This study reports the kinetics and mechanism of Fe(III)-catalyzed oxidative decarboxylation and deamination of a series of acyclic (α-aminoisobutyric acid, α-(methylamino)isobutyric acid, alanine, norvaline, and 2-aminobutyric acid) and cyclic (1-aminocyclopropane-1-carboxylic acid, 1-amino-1-cyclobutanecarboxylic acid, 1-aminocyclopentanecarboxylic acid, and 1-aminocyclohexanecarboxylicacid) amino acids using hydrogen peroxide, t-butyl hydroperoxide, iodosylbenzene, m-chloroperbenzoic acid, and peroxomonosulphate as oxidant in 75% DMF-25% water solvent mixture. Model complex [FeIVO(SALEN)]•+ (SALENH2: N,N′-bis(salicylidene)ethylenediamine) was generated by the reaction of FeIII(SALEN)Cl and H2O2 in CH3CN at 278 K as reported earlier. This method provided us high-valent oxoiron species, stable enough to ensure the direct observation of the reaction with amino acids.

Original languageEnglish
Pages (from-to)46-52
Number of pages7
JournalJournal of Inorganic Biochemistry
Volume123
DOIs
Publication statusPublished - Jun 2013

Fingerprint

ethylenediamine
Acyclic Acids
Cycloleucine
Iron
Aminoisobutyric Acids
tert-Butylhydroperoxide
Amino Acids
Oxidation
Deamination
Catalysts
Decarboxylation
Oxidants
Alanine
Hydrogen Peroxide
Observation
Kinetics
Acids
Water
1-aminocyclopropane-1-carboxylic acid
norvaline

Keywords

  • ACC oxidase
  • Amino acids
  • Catalysis
  • Iron
  • Oxidation
  • Salen

ASJC Scopus subject areas

  • Biochemistry
  • Inorganic Chemistry

Cite this

Bio-inspired amino acid oxidation by a non-heme iron catalyst. / Góger, Szabina; Bogáth, Dóra; Baráth, Gábor; Simaan, A. Jalila; Speier, G.; Kaizer, J.

In: Journal of Inorganic Biochemistry, Vol. 123, 06.2013, p. 46-52.

Research output: Contribution to journalArticle

Góger, Szabina ; Bogáth, Dóra ; Baráth, Gábor ; Simaan, A. Jalila ; Speier, G. ; Kaizer, J. / Bio-inspired amino acid oxidation by a non-heme iron catalyst. In: Journal of Inorganic Biochemistry. 2013 ; Vol. 123. pp. 46-52.
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