Evidence for a radical mechanism of halogenation of monochlorodimedone catalyzed by chloroperoxidase

Archives of Biochemistry and Biophysics
B W Griffin, P L Ashley

Abstract

A radical species of monochlorodimedone has been characterized by its high reactivity with molecular O2. Horseradish peroxidase greatly accelerated O2 uptake by acidic solutions of this substrate; the enzymatic reaction required exogenous H2O2 only with freshly prepared substrate solutions, and the total substrate oxidized was equal to the sum of H2O2 added and O2 consumed. However, with excess Br- and horseradish peroxidase, or high Br- or Cl- and chloroperoxidase, a 1:1 stoichiometry between H2O2 and substrate was observed. In the absence of halide, the stoichiometry of the chloroperoxidase-catalyzed oxidation of monochlorodimedone changed to two molecules of the organic donor per H2O2. Moreover, in the absence of halide, at substrate:H2O2 ratios greater than 2.0, chloroperoxidase catalyzed significant O2 uptake; this enzyme-dependent autoxidation of monochlorodimedone also occurred in the presence of Cl- or Br-, when H2O2 was limiting. These data, and recent evidence from this laboratory for free hypohalous acid as the first product of chloroperoxidase-catalyzed halide oxidation [B. W. Griffin (1983) Biochem. Biophys. Res. Commun. 116, 873-879], strongly support a mixed enzymatic/nonenzymatic radical chain process as the mec...Continue Reading

References

Aug 1, 1976·Archives of Biochemistry and Biophysics·G D NordblomM J Coon
Jan 1, 1976·Annual Review of Biochemistry·M Morrison, G R Schonbaum
Nov 15, 1983·Biochemical and Biophysical Research Communications·B W Griffin
Aug 1, 1981·Archives of Biochemistry and Biophysics·P L Ashley, B W Griffin
Nov 28, 1980·Biochemical and Biophysical Research Communications·P L AshleyB W Griffin

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Citations

Nov 23, 1988·Biochimica Et Biophysica Acta·A J Kettle, C C Winterbourn
Mar 4, 2005·Proceedings of the National Academy of Sciences of the United States of America·Ellen YehChristopher T Walsh
May 15, 1985·Archives of Biochemistry and Biophysics·B W Griffin, R Haddox
Mar 19, 2020·Biomolecular Concepts·Kelath Murali ManojKannan Pakshirajan
Jan 29, 2008·Biochemistry·Kelath Murali Manoj, Lowell P Hager
Jan 1, 1987·Archives of Biochemistry and Biophysics·H B DunfordM Pickard

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