Catalytic carbon–carbon bond cleavage in lignin via manganese–zirconium-mediated autoxidation
Abstract Efforts to produce aromatic monomers through catalytic lignin depolymerization have historically focused on aryl–ether bond cleavage. A large fraction of aromatic monomers in lignin, however, are linked by various carbon–carbon (C–C) bonds that are more challenging to cleave and limit the y...
| Main Authors: | , , , , , , , , , , , , |
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| Format: | Article |
| Language: | English |
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Nature Portfolio
2024-01-01
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| Series: | Nature Communications |
| Online Access: | https://doi.org/10.1038/s41467-024-45038-z |
| _version_ | 1827326916282023936 |
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| author | Chad T. Palumbo Nina X. Gu Alissa C. Bleem Kevin P. Sullivan Rui Katahira Lisa M. Stanley Jacob K. Kenny Morgan A. Ingraham Kelsey J. Ramirez Stefan J. Haugen Caroline R. Amendola Shannon S. Stahl Gregg T. Beckham |
| author_facet | Chad T. Palumbo Nina X. Gu Alissa C. Bleem Kevin P. Sullivan Rui Katahira Lisa M. Stanley Jacob K. Kenny Morgan A. Ingraham Kelsey J. Ramirez Stefan J. Haugen Caroline R. Amendola Shannon S. Stahl Gregg T. Beckham |
| author_sort | Chad T. Palumbo |
| collection | DOAJ |
| description | Abstract Efforts to produce aromatic monomers through catalytic lignin depolymerization have historically focused on aryl–ether bond cleavage. A large fraction of aromatic monomers in lignin, however, are linked by various carbon–carbon (C–C) bonds that are more challenging to cleave and limit the yields of aromatic monomers from lignin depolymerization. Here, we report a catalytic autoxidation method to cleave C–C bonds in lignin-derived dimers and oligomers from pine and poplar. The method uses manganese and zirconium salts as catalysts in acetic acid and produces aromatic carboxylic acids as primary products. The mixtures of the oxygenated monomers are efficiently converted to cis,cis-muconic acid in an engineered strain of Pseudomonas putida KT2440 that conducts aromatic O-demethylation reactions at the 4-position. This work demonstrates that autoxidation of lignin with Mn and Zr offers a catalytic strategy to increase the yield of valuable aromatic monomers from lignin. |
| first_indexed | 2024-03-07T14:53:22Z |
| format | Article |
| id | doaj.art-4af11bcfb84a4cdd8637b29f91da4cef |
| institution | Directory Open Access Journal |
| issn | 2041-1723 |
| language | English |
| last_indexed | 2024-03-07T14:53:22Z |
| publishDate | 2024-01-01 |
| publisher | Nature Portfolio |
| record_format | Article |
| series | Nature Communications |
| spelling | doaj.art-4af11bcfb84a4cdd8637b29f91da4cef2024-03-05T19:34:51ZengNature PortfolioNature Communications2041-17232024-01-0115111210.1038/s41467-024-45038-zCatalytic carbon–carbon bond cleavage in lignin via manganese–zirconium-mediated autoxidationChad T. Palumbo0Nina X. Gu1Alissa C. Bleem2Kevin P. Sullivan3Rui Katahira4Lisa M. Stanley5Jacob K. Kenny6Morgan A. Ingraham7Kelsey J. Ramirez8Stefan J. Haugen9Caroline R. Amendola10Shannon S. Stahl11Gregg T. Beckham12Renewable Resources and Enabling Sciences Center, National Renewable Energy LaboratoryRenewable Resources and Enabling Sciences Center, National Renewable Energy LaboratoryRenewable Resources and Enabling Sciences Center, National Renewable Energy LaboratoryRenewable Resources and Enabling Sciences Center, National Renewable Energy LaboratoryRenewable Resources and Enabling Sciences Center, National Renewable Energy LaboratoryRenewable Resources and Enabling Sciences Center, National Renewable Energy LaboratoryRenewable Resources and Enabling Sciences Center, National Renewable Energy LaboratoryRenewable Resources and Enabling Sciences Center, National Renewable Energy LaboratoryRenewable Resources and Enabling Sciences Center, National Renewable Energy LaboratoryRenewable Resources and Enabling Sciences Center, National Renewable Energy LaboratoryRenewable Resources and Enabling Sciences Center, National Renewable Energy LaboratoryDepartment of Chemistry, University of Wisconsin-MadisonRenewable Resources and Enabling Sciences Center, National Renewable Energy LaboratoryAbstract Efforts to produce aromatic monomers through catalytic lignin depolymerization have historically focused on aryl–ether bond cleavage. A large fraction of aromatic monomers in lignin, however, are linked by various carbon–carbon (C–C) bonds that are more challenging to cleave and limit the yields of aromatic monomers from lignin depolymerization. Here, we report a catalytic autoxidation method to cleave C–C bonds in lignin-derived dimers and oligomers from pine and poplar. The method uses manganese and zirconium salts as catalysts in acetic acid and produces aromatic carboxylic acids as primary products. The mixtures of the oxygenated monomers are efficiently converted to cis,cis-muconic acid in an engineered strain of Pseudomonas putida KT2440 that conducts aromatic O-demethylation reactions at the 4-position. This work demonstrates that autoxidation of lignin with Mn and Zr offers a catalytic strategy to increase the yield of valuable aromatic monomers from lignin.https://doi.org/10.1038/s41467-024-45038-z |
| spellingShingle | Chad T. Palumbo Nina X. Gu Alissa C. Bleem Kevin P. Sullivan Rui Katahira Lisa M. Stanley Jacob K. Kenny Morgan A. Ingraham Kelsey J. Ramirez Stefan J. Haugen Caroline R. Amendola Shannon S. Stahl Gregg T. Beckham Catalytic carbon–carbon bond cleavage in lignin via manganese–zirconium-mediated autoxidation Nature Communications |
| title | Catalytic carbon–carbon bond cleavage in lignin via manganese–zirconium-mediated autoxidation |
| title_full | Catalytic carbon–carbon bond cleavage in lignin via manganese–zirconium-mediated autoxidation |
| title_fullStr | Catalytic carbon–carbon bond cleavage in lignin via manganese–zirconium-mediated autoxidation |
| title_full_unstemmed | Catalytic carbon–carbon bond cleavage in lignin via manganese–zirconium-mediated autoxidation |
| title_short | Catalytic carbon–carbon bond cleavage in lignin via manganese–zirconium-mediated autoxidation |
| title_sort | catalytic carbon carbon bond cleavage in lignin via manganese zirconium mediated autoxidation |
| url | https://doi.org/10.1038/s41467-024-45038-z |
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