Mechanism of aromatic ring cleavage of a. beta. -biphenylyl ether dimer catalyzed by lignin peroxidase of Phanerochaete chrysosporium

Miki, K; Kondo, R; Renganathan, V; Mayfield, M B; Gold, M H

doi:10.1021/bi00413a031

Title: Mechanism of aromatic ring cleavage of a. beta. -biphenylyl ether dimer catalyzed by lignin peroxidase of Phanerochaete chrysosporium

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Abstract

Homogeneous lignin peroxidase (LiP) oxidized 1-(4-methoxyphenyl)-2-)2,6-dimethoxy-4-phenylphenoxy)-1,3-propanediol (I) to yield 1-(4-methoxyphenyl)-1,2,3-propanetriol (II), ..cap alpha..-(4-methoxy-phenyl)-2-oxo-1,3-dioxolane-4-methanol (III), 5-(4-methoxyphenyl)-2-oxo-1,3-dioxolane-4-methanol (IV), 4-oxo-3-phenyl-2-butenoic acid methyl ester (V), 5-hydroxy-4-phenyl-2(5H)-furanone (VI), 4-oxo-3-phenyl-2-pentenedioic acid dimethyl ester (VII), and 5-carbomethoxy-5-hydroxy-4-phenyl-2(5H)-furanone (VIII). Products II-VIII are all derived from the opening of the B aromatic ring of the substrate. Oxidation of I in H/sub 2/ /sup 18/O resulted in 87% and 65% incorporation of /sup 18/O into the carbonyl oxygen of III and IV, respectively. Oxidation of I under /sup 18/O/sub 2/ resulted in the incorporation of two atoms of oxygen into the aldehyde (V). Oxidation of I under either /sup 18/O/sub 2/ or H/sub 2//sup 18/O resulted in the incorporation of three atoms of oxygen into the lactol VI. Finally, oxidation of I under either /sup 18/O/sub 2/ or H/sub 2//sup 18/O indicated that four atoms of oxygen were incorporated into the lactol VIII. These results are explained by a mechanism involving the one-electron oxidation of the B ring of the substrate to an aryl cation radical by the H/sub 2/O/sub 2/ oxidized enzyme. In these oxidative pathways, only the formation of the aryl cation radical is enzyme-catalyzed. Subsequent reactions appear to be nonenzymatic, accounting for the variety of ring-opened productsmore » formed.« less

Authors:: Miki, K; Kondo, R; Renganathan, V; Mayfield, M B; Gold, M H

Publication Date:: Tue Jun 28 00:00:00 EDT 1988

Research Org.:: Oregon Graduate Center, Beaverton (USA)

OSTI Identifier:: 6769179

DOE Contract Number:: FG06-86ER13550

Resource Type:: Journal Article

Journal Name:: Biochemistry; (United States)

Additional Journal Information:: Journal Volume: 27:13

Country of Publication:: United States

Language:: English

Subject:: 59 BASIC BIOLOGICAL SCIENCES; AROMATICS; MOLECULAR STRUCTURE; OXIDATION; PEROXIDASES; BIOCHEMISTRY; BIOLOGICAL PATHWAYS; DIMERS; LABELLED COMPOUNDS; LIGNIN; OXYGEN 18; PHANEROCHAETE; WATER; CARBOHYDRATES; CHEMICAL REACTIONS; CHEMISTRY; ENZYMES; EVEN-EVEN NUCLEI; FUNGI; HYDROGEN COMPOUNDS; ISOTOPES; LIGHT NUCLEI; NUCLEI; ORGANIC COMPOUNDS; OXIDOREDUCTASES; OXYGEN COMPOUNDS; OXYGEN ISOTOPES; PLANTS; POLYSACCHARIDES; SACCHARIDES; STABLE ISOTOPES; 550201* - Biochemistry- Tracer Techniques

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                    Miki, K, Kondo, R, Renganathan, V, Mayfield, M B, and Gold, M H. Mechanism of aromatic ring cleavage of a. beta. -biphenylyl ether dimer catalyzed by lignin peroxidase of Phanerochaete chrysosporium.  United States: N. p., 1988. 
        Web.  doi:10.1021/bi00413a031.

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                    Miki, K, Kondo, R, Renganathan, V, Mayfield, M B, & Gold, M H. Mechanism of aromatic ring cleavage of a. beta. -biphenylyl ether dimer catalyzed by lignin peroxidase of Phanerochaete chrysosporium.  United States.  https://doi.org/10.1021/bi00413a031

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                    Miki, K, Kondo, R, Renganathan, V, Mayfield, M B, and Gold, M H. 1988.  
        "Mechanism of aromatic ring cleavage of a. beta. -biphenylyl ether dimer catalyzed by lignin peroxidase of Phanerochaete chrysosporium".  United States.  https://doi.org/10.1021/bi00413a031.

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@article{osti_6769179,

  title        = {Mechanism of aromatic ring cleavage of a. beta. -biphenylyl ether dimer catalyzed by lignin peroxidase of Phanerochaete chrysosporium},

  author       = {Miki, K and Kondo, R and Renganathan, V and Mayfield, M B and Gold, M H},

  abstractNote = {Homogeneous lignin peroxidase (LiP) oxidized 1-(4-methoxyphenyl)-2-)2,6-dimethoxy-4-phenylphenoxy)-1,3-propanediol (I) to yield 1-(4-methoxyphenyl)-1,2,3-propanetriol (II), ..cap alpha..-(4-methoxy-phenyl)-2-oxo-1,3-dioxolane-4-methanol (III), 5-(4-methoxyphenyl)-2-oxo-1,3-dioxolane-4-methanol (IV), 4-oxo-3-phenyl-2-butenoic acid methyl ester (V), 5-hydroxy-4-phenyl-2(5H)-furanone (VI), 4-oxo-3-phenyl-2-pentenedioic acid dimethyl ester (VII), and 5-carbomethoxy-5-hydroxy-4-phenyl-2(5H)-furanone (VIII). Products II-VIII are all derived from the opening of the B aromatic ring of the substrate. Oxidation of I in H/sub 2/ /sup 18/O resulted in 87% and 65% incorporation of /sup 18/O into the carbonyl oxygen of III and IV, respectively. Oxidation of I under /sup 18/O/sub 2/ resulted in the incorporation of two atoms of oxygen into the aldehyde (V). Oxidation of I under either /sup 18/O/sub 2/ or H/sub 2//sup 18/O resulted in the incorporation of three atoms of oxygen into the lactol VI. Finally, oxidation of I under either /sup 18/O/sub 2/ or H/sub 2//sup 18/O indicated that four atoms of oxygen were incorporated into the lactol VIII. These results are explained by a mechanism involving the one-electron oxidation of the B ring of the substrate to an aryl cation radical by the H/sub 2/O/sub 2/ oxidized enzyme. In these oxidative pathways, only the formation of the aryl cation radical is enzyme-catalyzed. Subsequent reactions appear to be nonenzymatic, accounting for the variety of ring-opened products formed.},

  doi          = {10.1021/bi00413a031},

  url          = {https://www.osti.gov/biblio/6769179},
  journal      = {Biochemistry; (United States)},
number       = ,

  volume       = 27:13,

  place        = {United States},

  year         = {Tue Jun 28 00:00:00 EDT 1988},

  month        = {Tue Jun 28 00:00:00 EDT 1988}

}

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