Oxidation of Azo Dyes by Peroxidase: Additional Evidence of a One-Electron Mechanism of Oxidation of Dimethylaminoazobenzene and Sudan I (Solvent Yellow 14)

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Title:Oxidation of Azo Dyes by Peroxidase: Additional Evidence of a One-Electron Mechanism of Oxidation of Dimethylaminoazobenzene and Sudan I (Solvent Yellow 14)
Creators:
Stiborová, Marie
Asfaw, Befekadu
Frei, Eva
Schmeiser, Heinz H.
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 61, 6, pp. 962-972
Uncontrolled Keywords:Azo dyes, Peroxidase, Oxidation, Radicals

Abstract

In the presence of hydrogen peroxide, peroxidase oxidized aminoazo dyes, the non-aminoazo dye 1-phenylazo-2-hydroxynaphthalene (Sudan I, Solvent Yellow 14), and its <i>C</i>-hydroxy derivatives. The oxidation of azo dyes is a pH-dependent reaction; while slightly acidic conditions are optimal for the aminoazo dyes, a basic pH suits better for Sudan I and its hydroxy derivatives. The oxidation of the carcinogenic Sudan I and dimethylaminoazobenzene catalyzed by peroxidase was investigated in detail. Oxygen consumption was not observed in incubations of peroxidase, azo dyes and hydrogen peroxide. However, oxygen uptake was observed after the addition of glutathione, which indicates that free radical metabolites of these compounds are formed by peroxidase. The results suggest that peroxidase metabolizes Sudan I and dimethylaminoazobenzene through a one-electron oxidation mechanism, giving rise to free radicals. Three of the products of Sudan I oxidation by peroxidase with a hitherto unknown structure were characterized partly by UV/VIS and mass spectroscopy.

Title:Oxidation of Azo Dyes by Peroxidase: Additional Evidence of a One-Electron Mechanism of Oxidation of Dimethylaminoazobenzene and Sudan I (Solvent Yellow 14)
Creators:
Stiborová, Marie
Asfaw, Befekadu
Frei, Eva
Schmeiser, Heinz H.
Uncontrolled Keywords:Azo dyes, Peroxidase, Oxidation, Radicals
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:61
Number:6
Page Range:pp. 962-972
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19960962UNSPECIFIED
ID Code:999
Item Type:Article
Deposited On:06 Feb 2009 17:05
Last Modified:06 Feb 2009 16:05

Citation

Stiborová, Marie; Asfaw, Befekadu; Frei, Eva; Schmeiser, Heinz H. (1996) Oxidation of Azo Dyes by Peroxidase: Additional Evidence of a One-Electron Mechanism of Oxidation of Dimethylaminoazobenzene and Sudan I (Solvent Yellow 14). Collection of Czechoslovak Chemical Communications, 61 (6). pp. 962-972. ISSN 0010-0765

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