Production of Valuable Phenolic Compounds from Lignin by Biocatalysis: State‐of‐the‐Art Perspective

Maenpuen, Somchart; Tinikul, Ruchanok; Chenprakhon, Pirom; Chaiyen, Pimchai

doi:10.1002/9783527803293.ch7

Cited by 4 publications

(10 citation statements)

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“…These compounds make up a significant part of lignocelluose, various natural products, and man-made chemicals, and have a wide spectrum of applications in chemical, agricultural, food, and pharmaceutical industries. [1][2][3] Many phenolic acids have useful biological activities such as antioxidant, anticancer, antimicrobial, antifungal, and anti-inflammatory activities, and are widely used in the pharmaceutical and food industries. 3 Hydroxylation of phenolic acid can generally increase the radical scavenging ability of the compound and may also increase other biological activities.…”

Section: Introductionmentioning

confidence: 99%

Monooxygenation of aromatic compounds by flavin‐dependent monooxygenases

2018

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Many flavoenzymes catalyze hydroxylation of aromatic compounds especially phenolic compounds have been isolated and characterized. These enzymes can be classified as either single-component or two-component flavin-dependent hydroxylases (monooxygenases). The hydroxylation reactions catalyzed by the enzymes in this group are useful for modifying the biological properties of phenolic compounds. This review aims to provide an in-depth discussion of the current mechanistic understanding of representative flavin-dependent monooxygenases including 3-hydroxy-benzoate 4-hydroxylase (PHBH, a single-component hydroxylase), 3-hydroxyphenylacetate 4-hydroxylase (HPAH, a two-component hydroxylase), and other monooxygenases which catalyze reactions in addition to hydroxylation, including 2-methyl-3-hydroxypyridine-5-carboxylate oxygenase (MHPCO, a single-component enzyme that catalyzes aromatic-ring cleavage), and HadA monooxygenase (a two-component enzyme that catalyzes additional group elimination reaction). These enzymes have different unique structural features which dictate their reactivity toward various substrates and influence their ability to stabilize flavin intermediates such as C4a-hydroperoxyflavin. Understanding the key catalytic residues and the active site environments important for governing enzyme reactivity will undoubtedly facilitate future work in enzyme engineering or enzyme redesign for the development of biocatalytic methods for the synthesis of valuable compounds.

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Section: Introductionmentioning

confidence: 99%

Monooxygenation of aromatic compounds by flavin‐dependent monooxygenases

2018

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“…Our review in this section focuses on biotransformation using enzymes to convert abundant and low-value PAs into high-value compounds, i.e., food additives, active pharmaceutical ingredients, monomers for materials, and specialty chemicals (Table ). More comprehensive reviews of bioconversion of phenolic acids to valuable chemicals can be found in other recently published reviews. ,,, …”

Section: Production Of Lignocellulosic Biomass-derived Productsmentioning

confidence: 99%

“…Lignin is a phenolic polymer which is composed of three major phenylpropanol units, namely p-coumaryl alcohol, coniferyl alcohol, and sinapyl alcohol (Figure 3D). 59,60 Depolymerization of lignin using either chemical, physicochemical, or biological processes or combined processes can liberate substantial amounts of phenolic monomers including monomeric phenols, phenolic aldehydes, and phenolic acids (Figure 3E). 61−64 The phenolic monomers are generally obtained as mixed compounds, in which their specific structures depend upon the depolymerization method used and the plant sources.…”

Section: Biobased Feedstocks Derived From Organic and Digested Wastesmentioning

confidence: 99%

“…More comprehensive reviews of bioconversion of phenolic acids to valuable chemicals can be found in other recently published reviews. 59,61,290,291 2.2.1. Food Additives.…”

Section: Phenolic Acid-derived Productsmentioning

confidence: 99%

“…Lignin is a phenolic polymer which is composed of three major phenylpropanol units, namely p -coumaryl alcohol, coniferyl alcohol, and sinapyl alcohol (Figure D). , Depolymerization of lignin using either chemical, physicochemical, or biological processes or combined processes can liberate substantial amounts of phenolic monomers including monomeric phenols, phenolic aldehydes, and phenolic acids (Figure E). − The phenolic monomers are generally obtained as mixed compounds, in which their specific structures depend upon the depolymerization method used and the plant sources . A method enabling reductive catalytic fractionation (RCF), known as the lignin-first approach, has recently been developed as a one-pot process for extraction and in situ catalytic conversion of the lignin released from lignocellulose into aromatic monomers. , The method enables extraction and catalytic processing of lignin to obtain high yields of aromatic monomers without modifying their structures.…”

Section: Introductionmentioning

confidence: 99%

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Enzymes, In Vivo Biocatalysis, and Metabolic Engineering for Enabling a Circular Economy and Sustainability

et al. 2021

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Since the industrial revolution, the rapid growth and development of global industries have depended largely upon the utilization of coal-derived chemicals, and more recently, the utilization of petroleum-based chemicals. These developments have followed a linear economy model (produce, consume, and dispose). As the world is facing a serious threat from the climate change crisis, a more sustainable solution for manufacturing, i.e., circular economy in which waste from the same or different industries can be used as feedstocks or resources for production offers an attractive industrial/business model. In nature, biological systems, i.e., microorganisms routinely use their enzymes and metabolic pathways to convert organic and inorganic wastes to synthesize biochemicals and energy required for their growth. Therefore, an understanding of how selected enzymes convert biobased feedstocks into special (bio)chemicals serves as an important basis from which to build on for applications in biocatalysis, metabolic engineering, and synthetic biology to enable biobased processes that are greener and cleaner for the environment. This review article highlights the current state of knowledge regarding the enzymatic reactions used in converting biobased wastes (lignocellulosic biomass, sugar, phenolic acid, triglyceride, fatty acid, and glycerol) and greenhouse gases (CO 2 and CH 4 ) into value-added products and discusses the current progress made in their metabolic engineering. The commercial aspects and life cycle assessment of products from enzymatic and metabolic engineering are also discussed. Continued development in the field of metabolic engineering would offer diversified solutions which are sustainable and renewable for manufacturing valuable chemicals.

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Vanadium-Containing Chloroperoxidase-Catalyzed Versatile Valorization of Phenols and Phenolic Acids

Li,

Duan,

Huang

et al. 2024

ACS Catal.

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The downstream product transformation of lignin depolymerization is of great interest in the production of highvalue aromatic chemicals. However, this transformation is often impeded by chemical oxidation under harsh reaction conditions. In this study, we demonstrate that hypohalites generated in situ by the vanadium-containing chloroperoxidase from Curvularia inaequalis (CiVCPO) can halogenate various electron-rich and electron-poor phenol and phenolic acid substrates. Specifically, CiVCPO enabled decarboxylative halogenation, deformylative halogenation, halogenation, and direct oxidation reactions. The versatile transformation routes for the valorization of phenolic compounds showed up to 99% conversion and 99% selectivity, with a turnover number of 60,700 and a turnover frequency of 60 s −1 for CiVCPO. This study potentially expands the biocatalytic toolbox for lignin valorization.

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Production of Valuable Phenolic Compounds from Lignin by Biocatalysis: State‐of‐the‐Art Perspective

Cited by 4 publications

References 81 publications

Monooxygenation of aromatic compounds by flavin‐dependent monooxygenases

Monooxygenation of aromatic compounds by flavin‐dependent monooxygenases

Enzymes, In Vivo Biocatalysis, and Metabolic Engineering for Enabling a Circular Economy and Sustainability

Vanadium-Containing Chloroperoxidase-Catalyzed Versatile Valorization of Phenols and Phenolic Acids

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