Multi-step biocatalytic depolymerization of lignin

Picart, Pere; Liu, Haifeng; Grande, Philipp M.; Anders, Nico; Zhu, Leilei; Klankermayer, Jürgen; Leitner, Walter; Marı́a, Pablo Domı́nguez de; Schwaneberg, Ulrich; Schallmey, Anett

doi:10.1007/s00253-017-8360-z

Cited by 56 publications

(44 citation statements)

References 48 publications

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“… 27 However, in the recent study the activity of LigE and N. aromaticivorans LigF-NA on laccase-oxidized OrganoCat beech wood lignin was reported. 30 This multistep biocatalytic lignin depolymerization process employed also a fourth enzyme, LigG-TD from Thiobacillus denitrificans , which is a glutathione lyase. LigG-TD catalyzes a GSH-dependent thioether cleavage of glutathione adduct formed by LigF and LigE.…”

Section: Resultsmentioning

confidence: 99%

Selective Cleavage of Lignin β-O-4 Aryl Ether Bond by β-Etherase of the White-Rot Fungus Dichomitus squalens

Marinovíc

Nousiainen

Dilokpimol

et al. 2018

ACS Sustainable Chem. Eng.

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Production of value-added compounds from a renewable aromatic polymer, lignin, has proven to be challenging. Chemical procedures, involving harsh reaction conditions, are costly and often result in nonselective degradation of lignin linkages. Therefore, enzymatic catalysis with selective cleavage of lignin bonds provides a sustainable option for lignin valorization. In this study, we describe the first functionally characterized fungal intracellular β-etherase from the wood-degrading white-rot basidiomycete Dichomitus squalens. This enzyme, Ds-GST1, from the glutathione-S-transferase superfamily selectively cleaved the β-O-4 aryl ether bond of a dimeric lignin model compound in a glutathione-dependent reaction. Ds-GST1 also demonstrated activity on polymeric synthetic lignin fractions, shown by a decrease in molecular weight distribution of the laccase-oxidized guaiacyl dehydrogenation polymer. In addition to a possible role of Ds-GST1 in intracellular catabolism of lignin-derived aromatic compounds, the cleavage of the most abundant linkages in lignin under mild reaction conditions makes this biocatalyst an attractive green alternative in biotechnological applications.

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Section: Resultsmentioning

confidence: 99%

Selective Cleavage of Lignin β-O-4 Aryl Ether Bond by β-Etherase of the White-Rot Fungus Dichomitus squalens

Marinovíc

Nousiainen

Dilokpimol

et al. 2018

ACS Sustainable Chem. Eng.

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“…In order to use a polymer like lignin as a source of valuable aromatics and other chemicals, it is necessary to develop new or improve on existing depolymerization strategies. Recently developed oxidative and hydrogenolytic depolymerization approaches are showing some promise for producing low-molecular-weight aromatics in near-theoretical yields ( 15 , 30 ), but there has also been considerable interest in exploring the biological production of aromatics from this renewable plant polymer ( 25 ). The use of the bacterial β-etherase pathway for biological depolymerization involves milder conditions that could result in the release of monomers, such as HPS and HPV, that are useful in their own right or extractable low-MW mixtures that could be further valorized ( 25 , 31 ).…”

Section: Discussionmentioning

confidence: 99%

“…Recently developed oxidative and hydrogenolytic depolymerization approaches are showing some promise for producing low-molecular-weight aromatics in near-theoretical yields ( 15 , 30 ), but there has also been considerable interest in exploring the biological production of aromatics from this renewable plant polymer ( 25 ). The use of the bacterial β-etherase pathway for biological depolymerization involves milder conditions that could result in the release of monomers, such as HPS and HPV, that are useful in their own right or extractable low-MW mixtures that could be further valorized ( 25 , 31 ). There is now a large amount of information on the types of model diaromatic substrates recognized by individual β-etherase enzymes in vitro , the products of their activity, and their structural or functional relationships to other known enzymes ( 27 , 32 ).…”

Section: Discussionmentioning

confidence: 99%

“…In vivo activity may be limited to aromatic dimers or small lignin oligomers due to restrictions in transporting large polymers into the bacterial cytoplasm, where the β-etherase pathway enzymes are found. Recently, modest recovery of low-molecular-mass aromatic compounds from lignin from a multistep enzymatic process that used a laccase mediator system, two β-etherases, and a glutathione lyase was reported ( 25 ). However, the size of lignin fragments that were subject to enzymatic cleavage was not determined, and it therefore remains unknown whether the β-etherases were active on only small or also large lignin oligomers.…”

Section: Introductionmentioning

confidence: 99%

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In Vitro Enzymatic Depolymerization of Lignin with Release of Syringyl, Guaiacyl, and Tricin Units

Gall

Kontur

Lan

et al. 2018

Appl Environ Microbiol

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New environmentally sound technologies are needed to derive valuable compounds from renewable resources. Lignin, an abundant polymer in terrestrial plants comprised predominantly of guaiacyl and syringyl monoaromatic phenylpropanoid units, is a potential natural source of aromatic compounds. In addition, the plant secondary metabolite tricin is a recently discovered and moderately abundant flavonoid in grasses. The most prevalent interunit linkage between guaiacyl, syringyl, and tricin units is the β-ether linkage. Previous studies have shown that bacterial β-etherase pathway enzymes catalyze glutathione-dependent cleavage of β-ether bonds in dimeric β-ether lignin model compounds. To date, however, it remains unclear whether the known β-etherase enzymes are active on lignin polymers. Here we report on enzymes that catalyze β-ether cleavage from bona fide lignin, under conditions that recycle the cosubstrates NAD+ and glutathione. Guaiacyl, syringyl, and tricin derivatives were identified as reaction products when different model compounds or lignin fractions were used as substrates. These results demonstrate an in vitro enzymatic system that can recycle cosubstrates while releasing aromatic monomers from model compounds as well as natural and engineered lignin oligomers. These findings can improve the ability to produce valuable aromatic compounds from a renewable resource like lignin.IMPORTANCE Many bacteria are predicted to contain enzymes that could convert renewable carbon sources into substitutes for compounds that are derived from petroleum. The β-etherase pathway present in sphingomonad bacteria could cleave the abundant β–O–4-aryl ether bonds in plant lignin, releasing a biobased source of aromatic compounds for the chemical industry. However, the activity of these enzymes on the complex aromatic oligomers found in plant lignin is unknown. Here we demonstrate biodegradation of lignin polymers using a minimal set of β-etherase pathway enzymes, the ability to recycle needed cofactors (glutathione and NAD+) in vitro, and the release of guaiacyl, syringyl, and tricin as depolymerized products from lignin. These observations provide critical evidence for the use and future optimization of these bacterial β-etherase pathway enzymes for industrial-level biotechnological applications designed to derive high-value monomeric aromatic compounds from lignin.

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“…The enzymatic cocktails secreted for lignin depolymerization by fungi, with Phanerochaete chrysosporium as the most investigated example, contain diverse radical enzymes, globally referred to as lignases [398]. Laccases and peroxidases must be highlighted among lignases [399][400][401], but alternative lignin-oxidizing enzymes exist, specifically in the case of lignin degradation by bacteria, such as Sphingobacterium sp. [402].…”

Section: Biological and Biochemical Processesmentioning

confidence: 99%

Alternatives for Chemical and Biochemical Lignin Valorization: Hot Topics from a Bibliometric Analysis of the Research Published During the 2000–2016 Period

2018

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A complete bibliometric analysis of the Scopus database was performed to identify the research trends related to lignin valorization from 2000 to 2016. The results from this analysis revealed an exponentially increasing number of publications and a high relevance of interdisciplinary collaboration. The simultaneous valorization of the three main components of lignocellulosic biomass (cellulose, hemicellulose, and lignin) has been revealed as a key aspect and optimal pretreatment is required for the subsequent lignin valorization. Research covers the determination of the lignin structure, isolation, and characterization; depolymerization by thermal and thermochemical methods; chemical, biochemical and biological conversion of depolymerized lignin; and lignin applications. Most methods for lignin depolymerization are focused on the selective cleavage of the β-O-4 linkage. Although many depolymerization methods have been developed, depolymerization with sodium hydroxide is the dominant process at industrial scale. Oxidative conversion of lignin is the most used method for the chemical lignin upgrading. Lignin uses can be classified according to its structure into lignin-derived aromatic compounds, lignin-derived carbon materials and lignin-derived polymeric materials. There are many advances in all approaches, but lignin-derived polymeric materials appear as a promising option.

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Multi-step biocatalytic depolymerization of lignin

Cited by 56 publications

References 48 publications

Selective Cleavage of Lignin β-O-4 Aryl Ether Bond by β-Etherase of the White-Rot Fungus Dichomitus squalens

Selective Cleavage of Lignin β-O-4 Aryl Ether Bond by β-Etherase of the White-Rot Fungus Dichomitus squalens

In Vitro Enzymatic Depolymerization of Lignin with Release of Syringyl, Guaiacyl, and Tricin Units

Alternatives for Chemical and Biochemical Lignin Valorization: Hot Topics from a Bibliometric Analysis of the Research Published During the 2000–2016 Period

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