Catalytic carbon–carbon bond cleavage in lignin via manganese–zirconium-mediated autoxidation

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 () and Gregg T. Beckham ()
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Chad T. Palumbo: National Renewable Energy Laboratory
Nina X. Gu: National Renewable Energy Laboratory
Alissa C. Bleem: National Renewable Energy Laboratory
Kevin P. Sullivan: National Renewable Energy Laboratory
Rui Katahira: National Renewable Energy Laboratory
Lisa M. Stanley: National Renewable Energy Laboratory
Jacob K. Kenny: National Renewable Energy Laboratory
Morgan A. Ingraham: National Renewable Energy Laboratory
Kelsey J. Ramirez: National Renewable Energy Laboratory
Stefan J. Haugen: National Renewable Energy Laboratory
Caroline R. Amendola: National Renewable Energy Laboratory
Shannon S. Stahl: University of Wisconsin-Madison
Gregg T. Beckham: National Renewable Energy Laboratory

Nature Communications, 2024, vol. 15, issue 1, 1-12

Abstract: 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.

Date: 2024
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DOI: 10.1038/s41467-024-45038-z

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