scholarly journals A Mechanistic Investigation of Acid-Catalyzed Cleavage of Aryl-Ether Linkages: Implications for Lignin Depolymerization in Acidic Environments

2013 ◽  
Vol 2 (3) ◽  
pp. 472-485 ◽  
Author(s):  
Matthew R. Sturgeon ◽  
Seonah Kim ◽  
Kelsey Lawrence ◽  
Robert S. Paton ◽  
Stephen C. Chmely ◽  
...  
Keyword(s):  
Aryl Ether ◽  
Mechanistic Investigation ◽  
Acid Catalyzed ◽  
Acidic Environments ◽  
Lignin Depolymerization

scholarly journals Aromatic dimer dehydrogenases from Novosphingobium aromaticivorans reduce monoaromatic diketones

2021 ◽  
Author(s):  
Alexandra M. Linz ◽  
Yanjun Ma ◽  
Jose M. Perez ◽  
Kevin S. Myers ◽  
Wayne S. Kontur ◽  
...  
Keyword(s):  
Potential Range ◽  
Industrial Chemicals ◽  
Multiple Substrates ◽  
Chemically Modified ◽  
Genome Wide ◽  
Wide Range ◽  
Acid Catalyzed ◽  
Plant Polymer ◽  
Lignin Depolymerization

Lignin is a potential source of valuable chemicals, but its chemical depolymerization results in a heterogeneous mixture of aromatics and other products. Microbes could valorize depolymerized lignin by converting multiple substrates into one or a small number of products. In this study, we describe the ability of Novosphingobium aromaticivorans to metabolize 1-(4-hydroxy-3-methoxyphenyl)propane-1,2-dione (G-diketone), an aromatic Hibbert diketone which is produced during formic acid-catalyzed lignin depolymerization. By assaying genome-wide transcript levels from N. aromaticivorans during growth on G-diketone and other chemically-related aromatics, we hypothesized that the Lig dehydrogenases, previously characterized as oxidizing β-O-4 linkages in aromatic dimers, were involved in G-diketone metabolism by N. aromaticivorans . Using purified N. aromaticivorans Lig dehydrogenases, we found that LigL, LigN, and LigD each reduced the Cα ketone of G-diketone in vitro but with different substrate specificities and rates. Furthermore, LigL, but not LigN or LigD, also reduced the Cα ketone of 2-hydroxy-1-(4-hydroxy-3-methoxyphenyl)propan-1-one (GP-1) in vitro , a derivative of G-diketone with the Cβ ketone reduced, when GP-1 was provided as a substrate. The newly identified activity of these Lig dehydrogenases expands the potential range of substrates utilized by N. aromaticivorans beyond what has been previously recognized. This is beneficial both for metabolizing a wide range of natural and non-native depolymerized lignin substrates and for engineering microbes and enzymes that are active with a broader range of aromatic compounds. Importance Lignin is a major plant polymer composed of aromatic units that have value as chemicals. However, the structure and composition of lignin has made it difficult to use this polymer as a renewable source of industrial chemicals. Bacteria like Novosphingobium aromaticivorans have the potential to make chemicals from lignin not only because of their natural ability to metabolize a variety of aromatics but also because there are established protocols to engineer N. aromaticivorans strains to funnel lignin-derived aromatics into valuable products. In this work, we report a newly discovered activity of previously characterized dehydrogenase enzymes with a chemically-modified byproduct of lignin depolymerization. We propose that the activity of N. aromaticivorans enzymes with both native lignin aromatics and those produced by chemical depolymerization will expand opportunities for producing industrial chemicals from the heterogenous components of this abundant plant polymer.

scholarly journals Advanced Model Compounds for Understanding Acid-Catalyzed Lignin Depolymerization: Identification of Renewable Aromatics and a Lignin-Derived Solvent

2016 ◽  
Vol 138 (28) ◽  
pp. 8900-8911 ◽  
Author(s):  
Ciaran W. Lahive ◽  
Peter J. Deuss ◽  
Christopher S. Lancefield ◽  
Zhuohua Sun ◽  
David B. Cordes ◽  
...  
Keyword(s):  
Model Compounds ◽  
Acid Catalyzed ◽  
Lignin Depolymerization ◽  
Advanced Model

Enhanced Acid-Catalyzed Lignin Depolymerization in a Continuous Reactor with Stable Activity

2020 ◽  
Vol 8 (10) ◽  
pp. 4096-4106
Author(s):  
Kakasaheb Y. Nandiwale ◽  
Andrew M. Danby ◽  
Anand Ramanathan ◽  
Raghunath V. Chaudhari ◽  
Ali Hussain Motagamwala ◽  
...  
Keyword(s):  
Continuous Reactor ◽  
Acid Catalyzed ◽  
Lignin Depolymerization

Mechanistic investigation inspired “on water” reaction for hydrobromic acid-catalyzed Friedel-Crafts-type reaction of β -naphthol and formaldehyde

2017 ◽  
Vol 38 (26) ◽  
pp. 2268-2275 ◽  
Author(s):  
Shanshan Cao ◽  
Haiyan Yuan ◽  
Yang Yang ◽  
Mang Wang ◽  
Xiaoying Zhang ◽  
...  
Keyword(s):  
Hydrobromic Acid ◽  
Type Reaction ◽  
Mechanistic Investigation ◽  
Acid Catalyzed

scholarly journals High-Efficient and Recyclable Magnetic Separable Catalyst for Catalytic Hydrogenolysis of β-O-4 Linkage in Lignin

Polymers ◽  
2018 ◽  
Vol 10 (10) ◽  
pp. 1077 ◽  
Author(s):  
Jingtao Huang ◽  
Chengke Zhao ◽  
Fachuang Lu
Keyword(s):  
Catalytic Performance ◽  
High Yield ◽  
Chemical Bonds ◽  
Aryl Ether ◽  
Structural Units ◽  
Great Abundance ◽  
High Efficient ◽  
Catalytic Hydrogenolysis ◽  
Potential Applications ◽  
Lignin Depolymerization

Lignin is recognized as a good sustainable material because of its great abundance and potential applications. At present, lignin hydrogenolysis is considered as a potential but challenging way to produce low-molecular-mass aromatic chemicals. The most common linkage between the structural units of lignin polymer is the β-O-4 aryl ether, which are primary or even only target chemical bonds for many degradation processes. Herein, a Pd-Fe3O4 composite was synthesized for catalytic hydrogenolysis of β-O-4 bond in lignin. The synthesized catalyst was characterized by XRD, XPS, and SEM and the lignin depolymerization products were analyzed by GC-MS. The catalyst showed good catalytic performance during the hydrogenolysis process, lignin dimer was degraded into monomers completely and a high yield of monomers was obtained by the hydrogenolysis of bagasse lignin. More importantly, the magnetic catalyst was separated conveniently by magnet after reaction and remained highly catalytically efficient after being reused for five times. This work has demonstrated an efficient & recyclable catalyst for the cleavage of the β-O-4 bond in lignin providing an alternative way to make better use of lignins.

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