Transformations of arylpropane lignin model compounds by a lignin peroxidase of the white-rot fungus Phanerochaete chrysosporium

Archives of Biochemistry and Biophysics
V B HuynhR Crawford

Abstract

Various lignin model compounds of the O-arylpropane type were oxidized with purified lignin peroxidase from the white-rot fungus Phanerochaete chrysosporium, and oxidation products were identified by gas-chromatography/mass-spectroscopy procedures. Our results are in accord with the theory that lignin peroxidase catalyzes one-electron oxidations of its substrates with formation of cation radicals, and that these radicals undergo degradative reactions that are predictable from a knowledge of cation radical and oxygen chemistry. Cation radicals formed from O-arylpropane model compounds appeared to undergo the following types of degradative transformations: addition of water to ring-centered radicals, followed by proton loss yielding quinones and alcohols; nucleophilic attack by hydroxy functions on propanoid moieties giving cyclic ketals as intermediates which decompose to yield side chain migration products; transfer of the charge of a radical from a ring to the associated alkyl moiety through an ether bond, with loss of a proton from the latter, forming a new carbon-centered radical. The new alkyl-centered radicals apparently were able to abduct dioxygen to form peroxyl radicals which decomposed giving a variety of oxidation pr...Continue Reading

References

Feb 1, 1986·Archives of Biochemistry and Biophysics·A PaszczyńskiR Crawford
Apr 1, 1986·Archives of Biochemistry and Biophysics·V RenganathanM H Gold
Apr 1, 1984·Proceedings of the National Academy of Sciences of the United States of America·M Tien, T K Kirk

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Citations

Dec 30, 1988·Biochemical and Biophysical Research Communications·I T ForresterG F Leatham
Feb 3, 2005·FEMS Microbiology Letters·Yong-Hak Kim, Karl-Heinrich Engesser
Jul 23, 1998·Critical Reviews in Biotechnology·S RajarathnamZ Bano
Jan 1, 1990·Critical Reviews in Biochemistry and Molecular Biology·F P Guengerich

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