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Oxidative cleavage of non-phenolic β-O-4 lignin model dimers by an extracellular aromatic peroxygenase
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| Zeitschriftentitel: | Holzforschung |
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| Personen und Körperschaften: | , , , , , , , |
| In: | Holzforschung, 65, 2011, 5 |
| Format: | E-Article |
| Sprache: | Unbestimmt |
| veröffentlicht: |
Walter de Gruyter GmbH
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| Schlagwörter: |
| author_facet |
Kinne, Matthias Poraj-Kobielska, Marzena Ullrich, René Nousiainen, Paula Sipilä, Jussi Scheibner, Katrin Hammel, Kenneth E. Hofrichter, Martin Kinne, Matthias Poraj-Kobielska, Marzena Ullrich, René Nousiainen, Paula Sipilä, Jussi Scheibner, Katrin Hammel, Kenneth E. Hofrichter, Martin |
|---|---|
| author |
Kinne, Matthias Poraj-Kobielska, Marzena Ullrich, René Nousiainen, Paula Sipilä, Jussi Scheibner, Katrin Hammel, Kenneth E. Hofrichter, Martin |
| spellingShingle |
Kinne, Matthias Poraj-Kobielska, Marzena Ullrich, René Nousiainen, Paula Sipilä, Jussi Scheibner, Katrin Hammel, Kenneth E. Hofrichter, Martin Holzforschung Oxidative cleavage of non-phenolic β-O-4 lignin model dimers by an extracellular aromatic peroxygenase Biomaterials |
| author_sort |
kinne, matthias |
| spelling |
Kinne, Matthias Poraj-Kobielska, Marzena Ullrich, René Nousiainen, Paula Sipilä, Jussi Scheibner, Katrin Hammel, Kenneth E. Hofrichter, Martin 1437-434X 0018-3830 Walter de Gruyter GmbH Biomaterials http://dx.doi.org/10.1515/hf.2011.057 <jats:title>Abstract</jats:title><jats:p>The extracellular aromatic peroxygenase of the agaric fungus<jats:italic>Agrocybe aegerita</jats:italic>catalyzed the H<jats:sub>2</jats:sub>O<jats:sub>2</jats:sub>-dependent cleavage of non-phenolic arylglycerol-<jats:italic>β</jats:italic>-aryl ethers (<jats:italic>β</jats:italic>-O-4 ethers). For instance 1-(3,4-dimethoxyphenyl)-2-(2-methoxy-phenoxy)propane-1,3-diol, a recalcitrant dimeric lignin model compound that represents the major non-phenolic substructure in lignin, was selectively<jats:italic>O</jats:italic>-demethylated at the<jats:italic>para</jats:italic>-methoxy group to give formaldehyde and 1-(4-hydroxy-3-methoxyphenyl)-2-(2-methoxyphenoxy)propane-1,3-diol. The phenol moiety of the latter compound was then enzymatically oxidized into phenoxy radicals and a quinoid cation, which initiated the autocatalytic cleavage of the dimer and the formation of monomers such as 2-methoxy-1,4-benzoquinone and phenoxyl-substituted propionic acid. The introduction of<jats:sup>18</jats:sup>O from H<jats:sub>2</jats:sub><jats:sup>18</jats:sup>O<jats:sub>2</jats:sub>and H<jats:sub>2</jats:sub><jats:sup>18</jats:sup>O at different positions into the pro-ducts provided information about the routes of ether cleavage. Studies with a<jats:sup>14</jats:sup>C-labeled lignin model dimer showed that more than 70% of the intermediates formed were further coupled to form polymers with molecular masses above 10 kDa. The results indicate that fungal aromatic peroxygenases may be involved in the bioconversion of methoxylated plant ingredients originating from lignin or other sources.</jats:p> Oxidative cleavage of non-phenolic β-O-4 lignin model dimers by an extracellular aromatic peroxygenase Holzforschung |
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10.1515/hf.2011.057 |
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Walter de Gruyter GmbH, 2011 |
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Walter de Gruyter GmbH, 2011 |
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1437-434X 0018-3830 |
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| title |
Oxidative cleavage of non-phenolic β-O-4 lignin model dimers by an extracellular aromatic peroxygenase |
| title_unstemmed |
Oxidative cleavage of non-phenolic β-O-4 lignin model dimers by an extracellular aromatic peroxygenase |
| title_full |
Oxidative cleavage of non-phenolic β-O-4 lignin model dimers by an extracellular aromatic peroxygenase |
| title_fullStr |
Oxidative cleavage of non-phenolic β-O-4 lignin model dimers by an extracellular aromatic peroxygenase |
| title_full_unstemmed |
Oxidative cleavage of non-phenolic β-O-4 lignin model dimers by an extracellular aromatic peroxygenase |
| title_short |
Oxidative cleavage of non-phenolic β-O-4 lignin model dimers by an extracellular aromatic peroxygenase |
| title_sort |
oxidative cleavage of non-phenolic β-o-4 lignin model dimers by an extracellular aromatic peroxygenase |
| topic |
Biomaterials |
| url |
http://dx.doi.org/10.1515/hf.2011.057 |
| publishDate |
2011 |
| physical |
|
| description |
<jats:title>Abstract</jats:title><jats:p>The extracellular aromatic peroxygenase of the agaric fungus<jats:italic>Agrocybe aegerita</jats:italic>catalyzed the H<jats:sub>2</jats:sub>O<jats:sub>2</jats:sub>-dependent cleavage of non-phenolic arylglycerol-<jats:italic>β</jats:italic>-aryl ethers (<jats:italic>β</jats:italic>-O-4 ethers). For instance 1-(3,4-dimethoxyphenyl)-2-(2-methoxy-phenoxy)propane-1,3-diol, a recalcitrant dimeric lignin model compound that represents the major non-phenolic substructure in lignin, was selectively<jats:italic>O</jats:italic>-demethylated at the<jats:italic>para</jats:italic>-methoxy group to give formaldehyde and 1-(4-hydroxy-3-methoxyphenyl)-2-(2-methoxyphenoxy)propane-1,3-diol. The phenol moiety of the latter compound was then enzymatically oxidized into phenoxy radicals and a quinoid cation, which initiated the autocatalytic cleavage of the dimer and the formation of monomers such as 2-methoxy-1,4-benzoquinone and phenoxyl-substituted propionic acid. The introduction of<jats:sup>18</jats:sup>O from H<jats:sub>2</jats:sub><jats:sup>18</jats:sup>O<jats:sub>2</jats:sub>and H<jats:sub>2</jats:sub><jats:sup>18</jats:sup>O at different positions into the pro-ducts provided information about the routes of ether cleavage. Studies with a<jats:sup>14</jats:sup>C-labeled lignin model dimer showed that more than 70% of the intermediates formed were further coupled to form polymers with molecular masses above 10 kDa. The results indicate that fungal aromatic peroxygenases may be involved in the bioconversion of methoxylated plant ingredients originating from lignin or other sources.</jats:p> |
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| author | Kinne, Matthias, Poraj-Kobielska, Marzena, Ullrich, René, Nousiainen, Paula, Sipilä, Jussi, Scheibner, Katrin, Hammel, Kenneth E., Hofrichter, Martin |
| author_facet | Kinne, Matthias, Poraj-Kobielska, Marzena, Ullrich, René, Nousiainen, Paula, Sipilä, Jussi, Scheibner, Katrin, Hammel, Kenneth E., Hofrichter, Martin, Kinne, Matthias, Poraj-Kobielska, Marzena, Ullrich, René, Nousiainen, Paula, Sipilä, Jussi, Scheibner, Katrin, Hammel, Kenneth E., Hofrichter, Martin |
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| description | <jats:title>Abstract</jats:title><jats:p>The extracellular aromatic peroxygenase of the agaric fungus<jats:italic>Agrocybe aegerita</jats:italic>catalyzed the H<jats:sub>2</jats:sub>O<jats:sub>2</jats:sub>-dependent cleavage of non-phenolic arylglycerol-<jats:italic>β</jats:italic>-aryl ethers (<jats:italic>β</jats:italic>-O-4 ethers). For instance 1-(3,4-dimethoxyphenyl)-2-(2-methoxy-phenoxy)propane-1,3-diol, a recalcitrant dimeric lignin model compound that represents the major non-phenolic substructure in lignin, was selectively<jats:italic>O</jats:italic>-demethylated at the<jats:italic>para</jats:italic>-methoxy group to give formaldehyde and 1-(4-hydroxy-3-methoxyphenyl)-2-(2-methoxyphenoxy)propane-1,3-diol. The phenol moiety of the latter compound was then enzymatically oxidized into phenoxy radicals and a quinoid cation, which initiated the autocatalytic cleavage of the dimer and the formation of monomers such as 2-methoxy-1,4-benzoquinone and phenoxyl-substituted propionic acid. The introduction of<jats:sup>18</jats:sup>O from H<jats:sub>2</jats:sub><jats:sup>18</jats:sup>O<jats:sub>2</jats:sub>and H<jats:sub>2</jats:sub><jats:sup>18</jats:sup>O at different positions into the pro-ducts provided information about the routes of ether cleavage. Studies with a<jats:sup>14</jats:sup>C-labeled lignin model dimer showed that more than 70% of the intermediates formed were further coupled to form polymers with molecular masses above 10 kDa. The results indicate that fungal aromatic peroxygenases may be involved in the bioconversion of methoxylated plant ingredients originating from lignin or other sources.</jats:p> |
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| institution | DE-D275, DE-Bn3, DE-Brt1, DE-D161, DE-Gla1, DE-Zi4, DE-15, DE-Pl11, DE-Rs1, DE-105, DE-14, DE-Ch1, DE-L229 |
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| spelling | Kinne, Matthias Poraj-Kobielska, Marzena Ullrich, René Nousiainen, Paula Sipilä, Jussi Scheibner, Katrin Hammel, Kenneth E. Hofrichter, Martin 1437-434X 0018-3830 Walter de Gruyter GmbH Biomaterials http://dx.doi.org/10.1515/hf.2011.057 <jats:title>Abstract</jats:title><jats:p>The extracellular aromatic peroxygenase of the agaric fungus<jats:italic>Agrocybe aegerita</jats:italic>catalyzed the H<jats:sub>2</jats:sub>O<jats:sub>2</jats:sub>-dependent cleavage of non-phenolic arylglycerol-<jats:italic>β</jats:italic>-aryl ethers (<jats:italic>β</jats:italic>-O-4 ethers). For instance 1-(3,4-dimethoxyphenyl)-2-(2-methoxy-phenoxy)propane-1,3-diol, a recalcitrant dimeric lignin model compound that represents the major non-phenolic substructure in lignin, was selectively<jats:italic>O</jats:italic>-demethylated at the<jats:italic>para</jats:italic>-methoxy group to give formaldehyde and 1-(4-hydroxy-3-methoxyphenyl)-2-(2-methoxyphenoxy)propane-1,3-diol. The phenol moiety of the latter compound was then enzymatically oxidized into phenoxy radicals and a quinoid cation, which initiated the autocatalytic cleavage of the dimer and the formation of monomers such as 2-methoxy-1,4-benzoquinone and phenoxyl-substituted propionic acid. The introduction of<jats:sup>18</jats:sup>O from H<jats:sub>2</jats:sub><jats:sup>18</jats:sup>O<jats:sub>2</jats:sub>and H<jats:sub>2</jats:sub><jats:sup>18</jats:sup>O at different positions into the pro-ducts provided information about the routes of ether cleavage. Studies with a<jats:sup>14</jats:sup>C-labeled lignin model dimer showed that more than 70% of the intermediates formed were further coupled to form polymers with molecular masses above 10 kDa. The results indicate that fungal aromatic peroxygenases may be involved in the bioconversion of methoxylated plant ingredients originating from lignin or other sources.</jats:p> Oxidative cleavage of non-phenolic β-O-4 lignin model dimers by an extracellular aromatic peroxygenase Holzforschung |
| spellingShingle | Kinne, Matthias, Poraj-Kobielska, Marzena, Ullrich, René, Nousiainen, Paula, Sipilä, Jussi, Scheibner, Katrin, Hammel, Kenneth E., Hofrichter, Martin, Holzforschung, Oxidative cleavage of non-phenolic β-O-4 lignin model dimers by an extracellular aromatic peroxygenase, Biomaterials |
| title | Oxidative cleavage of non-phenolic β-O-4 lignin model dimers by an extracellular aromatic peroxygenase |
| title_full | Oxidative cleavage of non-phenolic β-O-4 lignin model dimers by an extracellular aromatic peroxygenase |
| title_fullStr | Oxidative cleavage of non-phenolic β-O-4 lignin model dimers by an extracellular aromatic peroxygenase |
| title_full_unstemmed | Oxidative cleavage of non-phenolic β-O-4 lignin model dimers by an extracellular aromatic peroxygenase |
| title_short | Oxidative cleavage of non-phenolic β-O-4 lignin model dimers by an extracellular aromatic peroxygenase |
| title_sort | oxidative cleavage of non-phenolic β-o-4 lignin model dimers by an extracellular aromatic peroxygenase |
| title_unstemmed | Oxidative cleavage of non-phenolic β-O-4 lignin model dimers by an extracellular aromatic peroxygenase |
| topic | Biomaterials |
| url | http://dx.doi.org/10.1515/hf.2011.057 |