[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 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.
Shleev
S V
SV
Bach Institute of Biochemistry, Russian Academy of Sciences, Moscow, 119071 Russia.
Khan
I G
IG
Morozova
O V
OV
Mazhugo
Iu M
IuM
Khalunina
A S
AS
Iaropolov
A I
AI
D001487:Basidiomycota / Q000201:enzymology*; D001592:Benzyl Alcohols / Q000737:chemistry / Q000378:metabolism; D006735:Horseradish Peroxidase; D042845:Laccase / Q000737:chemistry / Q000378:metabolism; D010084:Oxidation-Reduction; D011720:Pyrazoles / Q000737:chemistry*; D047069:Pyrazolones; D014641:Vanillic Acid / Q000031:analogs & derivatives* / Q000737:chemistry; D015262:Xenobiotics / Q000737:chemistry / Q000378:metabolism*
D001592:Benzyl Alcohols; D011720:Pyrazoles; D047069:Pyrazolones; D015262:Xenobiotics; C009333:veratric acid; C038362:pyrazolone; D042845:Laccase; D006735:Horseradish Peroxidase; D014641:Vanillic Acid; C042197:veratryl alcohol