The impact of lignin sulfonation on its reactivity with laccase and laccase/HBT

Hilgers, Roelant; Twentyman-Jones, Megan; Dam, Annemieke van; Gruppen, Harry; Zuilhof, Han; Kabel, Mirjam A.; Vincken, Jean‐Paul

doi:10.1039/c9cy00249a

Cited by 15 publications

(26 citation statements)

References 32 publications

(41 reference statements)

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“…HPV/S and DHPV/S resulted from cleavage of the β-O and O-4′ bonds of β-O-4′ linkages, respectively, and have been reported in studies on LMSinduced degradation of dimeric lignin model compounds. 19,23,25 To the best of our knowledge, our research is the first to show evidence for such degradation pathways in a LMS treatment of actual lignocellulosic biomass.…”

Section: Detailed Insights Into Laccase/hbt Induced Reactions Of Ligninmentioning

confidence: 67%

“…This is further evidenced by model compound studies, in which HBT-coupling was observed with phenoxyl radicals, and not with benzylic radicals. 18,19 In addition to HBT grafting, phenoxyl radicals may also undergo radical coupling to other lignin-derived radicals (repolymerization). 18,63 Although no NMR based evidence could be obtained for this, SEC results indeed suggested that (re)polymerization of lignin occurred (Fig.…”

Section: Mechanisms Underlying Grass Delignification By Laccase/hbtmentioning

confidence: 99%

“…These pathways have, so far, mainly been investigated by using low molecular weight model compounds, resembling substructures of lignin. [18][19][20][21][22][23][24][25][26] Dependent on the structure of the lignin radical, bond cleavage, radical coupling and a number of other modifications have been reported, and it has been suggested that these reaction pathways are in competition with each other. Obviously, this competition determines whether LMS treatment eventually results in overall polymerization or depolymerization.…”

Section: Introductionmentioning

confidence: 99%

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Understanding laccase/HBT-catalyzed grass delignification at the molecular level

et al. 2020

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Section: Detailed Insights Into Laccase/hbt Induced Reactions Of Ligninmentioning

confidence: 67%

Section: Mechanisms Underlying Grass Delignification By Laccase/hbtmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Understanding laccase/HBT-catalyzed grass delignification at the molecular level

et al. 2020

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“…Laccases catalyze oxidation of lignin, initially producing a phenoxy radical ( Perna et al, 2019 ). It had often been reported that Cα-oxidation, rather than ether bond cleavage, was the main result of laccase-catalyzed lignin degradation system ( Heap et al, 2014 ; Hilgers et al, 2019 ). A non-phenolic lignin model, veratrylglycerol-β-guaiacyl ether (VBG), was used to explore the degradation of lignin by a laccase/HBT system.…”

Section: Discussionmentioning

confidence: 99%

A Novel Polyphenol Oxidoreductase OhLac from Ochrobactrum sp. J10 for Lignin Degradation

Yang

Wang

et al. 2021

Front. Microbiol.

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Identifying the enzymes involved in lignin degradation by bacteria is important in studying lignin valorization to produce renewable chemical products. In this paper, the catalytic oxidation of lignin by a novel multi-copper polyphenol oxidoreductase (OhLac) from the lignin degrader Ochrobactrum sp. J10 was explored. Following its expression, reconstitution, and purification, a recombinant enzyme OhLac was obtained. The OhLac enzyme was characterized kinetically against a range of substrates, including ABTS, guaiacol, and 2,6-DMP. Moreover, the effects of pH, temperature, and Cu2+ on OhLac activity and stability were determined. Gas chromatography-mass spectrometer (GC-MS) results indicated that the β-aryl ether lignin model compound guaiacylglycerol-β-guaiacyl ether (GGE) was oxidized by OhLac to generate guaiacol and vanillic acid. Molecular docking analysis of GGE and OhLac was then used to examine the significant amino residues and hydrogen bonding sites in the substrate–enzyme interaction. Altogether, we were able to investigate the mechanisms involved in lignin degradation. The breakdown of the lignocellulose materials wheat straw, corn stalk, and switchgrass by the recombinant OhLac was observed over 3 days, and the degradation results revealed that OhLac plays a key role in lignin degradation.

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“…From the previous work of the same group based on lignin model compounds, it was deduced that sulfonation of the αcarbon prevented unproductive radical coupling, thereby promoting polymerization. [51] A separate study of Hilgers et al [78] using model compounds further indicated that lignin sulfonation drives the overall outcome of laccase catalysis with lignin and mediator systems towards polymerization.…”

Section: Other Factors: Oxygen Supply Pre-treatment Degree Of Sulfonationmentioning

confidence: 99%

Laccase as a Tool in Building Advanced Lignin‐Based Materials

et al. 2021

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Lignin is an abundant natural feedstock that offers great potential as a renewable substitute for fossil-based resources. Its polyaromatic structure and unique properties have attracted significant research efforts. The advantages of an enzymatic over chemical or thermal approach to construct or deconstruct lignins are that it operates in mild conditions, requires less energy, and usually uses non-toxic chemicals. Laccase is a widely investigated oxidative enzyme that can catalyze the polymerization and depolymerization of lignin. Its dual nature causes a challenge in controlling the overall direction of ligninlaccase catalysis. In this Review, the factors that affect laccasecatalyzed lignin polymerization were summarized, evaluated, and compared to identify key features that favor lignin polymerization. In addition, a critical assessment of the conditions that enable production of novel lignin hybrids via laccase-catalyzed grafting was presented. To assess the industrial relevance of laccase-assisted lignin valorization, patented applications were surveyed and industrial challenges and opportunities were analyzed. Finally, our perspective in realizing the full potential of laccase in building lignin-based materials for advanced applications was deduced from analysis of the limitations governing laccase-assisted lignin polymerization and grafting.

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The impact of lignin sulfonation on its reactivity with laccase and laccase/HBT

Abstract: This study shows and explains how sulfonation of lignin influences its reactivity with laccase and LMS (with mediator HBT), and what consequences this has for the overall outcome of laccase and LMS treatments.

Cited by 15 publications

References 32 publications

Understanding laccase/HBT-catalyzed grass delignification at the molecular level

Understanding laccase/HBT-catalyzed grass delignification at the molecular level

A Novel Polyphenol Oxidoreductase OhLac from Ochrobactrum sp. J10 for Lignin Degradation

Laccase as a Tool in Building Advanced Lignin‐Based Materials

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