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Peroxidase-catalyzed oxidation of pentachlorophenol.

Abstract：

:Pentachlorophenol (PCP) was shown to function as a reducing substrate for horseradish peroxidase (HRP) and to stimulate the HRP-catalyzed reduction of 5-phenyl-4-penten-1-yl hydroperoxide (PPHP) to 5-phenyl-4-penten-1-ol. HRP catalyzed the hydroperoxide-dependent oxidation of PCP, using H2O2, PPHP, or ethyl hydroperoxide as substrates, as evidenced by UV spectroscopic and reverse phase HPLC analysis of reaction mixtures. The major oxidation product was tetrachloro-1,4-benzoquinone which was identified on the basis of electronic absorption spectroscopy, mass spectrometry, and cochromatography with authentic standard. HRP-catalyzed oxidation of PCP yielded relatively stable, ESR-detectable pentachlorophenoxyl radical intermediates whose ESR spectra consisted of a symmetrical single line without hyperfine structure. Substitution of natural abundance isotopically-labeled PCP with 13C-labeled PCP resulted in broadening of the ESR signal line width from 6.1 G to 13.5 G. ESR spin trapping studies, with alpha-(1-oxy-4-pyridyl)-N tert-butylnitrone (4-POBN) as the spin trap demonstrated identical spectra using natural abundance isotopically-labeled PCP versus 13C-labeled PCP, suggesting oxyl addition, rather than carbon-centered radical addition to 4-POBN. The computer simulation of the observed spectra is consistent with two distinct 4-POBN adducts, with relative abundances of approximately 3:1, and hyperfine coupling constants of alpha N = (14.61 G)/alpha H = 1.83 G and alpha N = (14.76 G)/alpha H = 5.21 G, respectively. Mechanisms for the hydroperoxide-dependent, HRP-catalyzed oxidation of PCP are presented that are consistent with these results.

journal_name

Chem Res Toxicol

journal_title

Chemical research in toxicology

authors

Samokyszyn VM,Freeman JP,Maddipati KR,Lloyd RV

doi

10.1021/tx00045a005

subject

Has Abstract

pub_date

1995-04-01 00:00:00

pages

349-55

issue

3

eissn

0893-228X

issn

1520-5010

journal_volume

8

pub_type

杂志文章

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