Phenyl pyrazolones--novel oxidoreductase redox-mediators for degradation of xenobiotics

An approach was developed to screening organic compounds for putative activity of redox mediators of oxidoreductases, including laccases and peroxidases, applicable for xenobiotic degradation. The study was carried out with a homogenous laccase preparation from the basidiomycete Trametes hirsuta and...

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Published inPrikladnaja biohimija i mikrobiologija Vol. 40; no. 2; p. 165
Main Authors Shleev, S V, Khan, I G, Morozova, O V, Mazhugo, Iu M, Khalunina, A S, Iaropolov, A I
Format Journal Article
LanguageRussian
Published Russia (Federation) 01.03.2004
Subjects
Basidiomycota - enzymology
Benzyl Alcohols - chemistry
Benzyl Alcohols - metabolism
Horseradish Peroxidase
Laccase - chemistry
Laccase - metabolism
Oxidation-Reduction
Pyrazoles - chemistry
Pyrazolones
Vanillic Acid - analogs & derivatives
Vanillic Acid - chemistry
Xenobiotics - chemistry
Xenobiotics - metabolism
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Summary:An approach was developed to screening organic compounds for putative activity of redox mediators of oxidoreductases, including laccases and peroxidases, applicable for xenobiotic degradation. The study was carried out with a homogenous laccase preparation from the basidiomycete Trametes hirsuta and horse-radish root peroxidase. Compounds belonging to 1-phenyl-3-methylpyrazolones were selected. Spectroscopic and electrochemical investigation of two of the compounds, sodium 1-phenyl-2,3-dimethyl-4-aminopyrazolon 5n(4)-methanesulfonate (PPNa) and 1-(3'-sulfophenyl)-3-methylpyrazolone (SPP), was performed. Electrochemical oxidation of both PPNa and SPP gave rise to high-potential intermediates capable of oxidizing veratryl alcohol; a lignin-modeling compound. Kinetic indices of these compounds were determined in enzymatic reactions with the presence of laccase. It was shown that enzymatic oxidation of SPP by laccase produced high-potential intermediates capable of oxidizing veratryl alcohol to veratric acid. Veratryl alcohol did not oxidize during enzymatic oxidation of SPP by peroxidase. This points to a difference between the mechanisms of enzymatic oxidation of PPNa and SPP by laccase and peroxidase.
ISSN:0555-1099