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

Szabina Góger , Dóra Bogáth , Gábor Baráth , A. Jalila Simaan (1) , Gabor Speier , Jozsef Kaizer

1 ISM2 - Institut des Sciences Moléculaires de Marseille

This study reports the kinetics and mechanism of Fe(III)-catalyzed oxidative decarboxylation and deamina-tion 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 [Fe IV O(SALEN)] •+ (SALENH 2 : N,N′-bis(salicylidene) ethylenediamine) was generated by the reaction of Fe III (SALEN)Cl and H 2 O 2 in CH 3 CN 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.

Domaines: Chimie

Szabina Góger, Dóra Bogáth, Gábor Baráth, A. Jalila Simaan, Gabor Speier, et al.. Bio-inspired amino acid oxidation by a non-heme iron catalyst. Journal of Inorganic Biochemistry, 2013, 123, pp.46-52. ⟨10.1016/j.jinorgbio.2013.02.007⟩. ⟨hal-02091420⟩