Glucose-Free <i>cis</i>,<i>cis</i>-Muconic Acid Production via New Metabolic Designs Corresponding to the Heterogeneity of Lignin

Sonoki, Tomonori; Takahashi, Kenji; Sugita, Haruka; Hatamura, Minami; Azuma, Yuta; Sato, Takumi; Suzuki, Sachio; Kamimura, Naofumi; Masai, Eiji

doi:10.1021/acssuschemeng.7b03597

Cited by 122 publications

(68 citation statements)

References 38 publications

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“…The demethylation of guaiacyl derivatives, for example, leads to catechols, which are present in numerous pharmaceuticals, pesticides, and flavors. Alternatively, catechols are converted by oxidation into muconic acid, which can be hydrogenated to adipic acid derivatives to be used in polymer synthesis …”

Section: Introductionmentioning

confidence: 99%

Exploring the Selective Demethylation of Aryl Methyl Ethers with a Pseudomonas Rieske Monooxygenase

et al. 2018

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Biocatalytic dealkylation of aryl methyl ethers is an attractive reaction for valorization of lignin components, as well as for deprotection of hydroxy functionalities in synthetic chemistry. We explored the demethylation of various aryl methyl ethers by using an oxidative demethylase from Pseudomonas sp. HR199. The Rieske monooxygenase VanA and its partner electron transfer protein VanB were recombinantly coexpressed in Escherichia coli and they constituted at least 25 % of the total protein content. Enzymatic transformations showed that VanB accepts NADH and NADPH as electron donors. The VanA–VanB system demethylates a number of aromatic substrates, the presence of a carboxylic acid moiety is essential, and the catalysis occurs selectively at the meta position to this carboxylic acid in the aromatic ring. The reaction is inhibited by the by‐product formaldehyde. Therefore, we tested three different cascade/tandem reactions for cofactor regeneration and formaldehyde elimination; in particular, conversion was improved by addition of formaldehyde dehydrogenase and formate dehydrogenase. Finally, the biocatalyst was applied for the preparation of protocatechuic acid from vanillic acid, giving a 77 % yield of the desired product. The described reaction may find application in the conversion of lignin components into diverse hydroxyaromatic building blocks and generally offers potential for new, mild methods for efficient unmasking of phenols.

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Section: Introductionmentioning

confidence: 99%

Exploring the Selective Demethylation of Aryl Methyl Ethers with a Pseudomonas Rieske Monooxygenase

et al. 2018

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“…ISTKB was shown to use 4-HBA for growth and production of polyhydroxyalkanoate biopolyesters [20]. Other examples include the biological funneling of 4-HBA into valuable catabolic pathway intermediates such as muconic acid, 2-pyrone-4,6-dicarboxylic acid, beta-ketoadipic acid, and isocinchomeronic acid using engineered strains of Novosphingobium aromaticivorans and Pseudomonas putida [21][22][23].…”

Section: -Hydroxybenzoic Acidmentioning

confidence: 99%

Strategies for the production of biochemicals in bioenergy crops

Lin

Eudes

2020

Biotechnol Biofuels

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Industrial crops are grown to produce goods for manufacturing. Rather than food and feed, they supply raw materials for making biofuels, pharmaceuticals, and specialty chemicals, as well as feedstocks for fabricating fiber, biopolymer, and construction materials. Therefore, such crops offer the potential to reduce our dependency on petrochemicals that currently serve as building blocks for manufacturing the majority of our industrial and consumer products. In this review, we are providing examples of metabolites synthesized in plants that can be used as bio-based platform chemicals for partial replacement of their petroleum-derived counterparts. Plant metabolic engineering approaches aiming at increasing the content of these metabolites in biomass are presented. In particular, we emphasize on recent advances in the manipulation of the shikimate and isoprenoid biosynthetic pathways, both of which being the source of multiple valuable compounds. Implementing and optimizing engineered metabolic pathways for accumulation of coproducts in bioenergy crops may represent a valuable option for enhancing the commercial value of biomass and attaining sustainable lignocellulosic biorefineries.

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“…SYK-6 strain also showed high cis,cis-muconic acid yield (45% mol/mol) with lignin monomers as substrates. 249 A cis,cis-muconic acid yield of 96% from guaiacol-based lignin was obtained using a metabolically engineered Amycolatopsis sp. ATCC 39116 strain.…”

Section: Biological Conversion Of Lignin To Monomer Chemical Precursomentioning

confidence: 99%

High value‐added monomer chemicals and functional bio‐based materials derived from polymeric components of lignocellulose by organosolv fractionation

Zhang

Cai

Qin

et al. 2019

Biofuels Bioprod Bioref

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Organosolv fractionation (OF) is a promising method for lignocellulosic biomass biorefining to produce biofuels, biochemicals, and biomaterials. The fractionated polymeric components may be good feedstocks to produce bio‐based materials such as green polymers via chemical or biological conversion. However, related work to specify the bio‐based materials production via organosolv fractionation of lignocellulosic biomass is relatively scarce. In this work we have provided a comprehensive review of typical organosolv fractionation for isolating cellulose, hemicelluloses, and lignin, as well as the high value‐added monomer chemicals and functional materials derived from the fractionated components and their potential applications developed in recent years, primarily including the modified cellulose fibers for polymer materials, cellulose nanocrystals (CNCs), polysaccharide‐derived platform precursors for synthesis of bio‐based polymers, lignin‐derived dispersants, surfactants, carbon materials, and hemicellulose‐derived functional materials, etc. This work suggests that organosolv fractionation of lignocellulosic biomass could be a good entry to biomass refinery for high value‐added and functional materials production. However, there are still many challenges that should be overcome in terms of the fundamental, technical, and economic aspects for the organosolv fractionation process, formation of precursor compounds, synthesis of the bio‐based materials, design of product properties and functions, and the integration of the entire process. © 2019 Society of Chemical Industry and John Wiley & Sons, Ltd

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Glucose-Free cis,cis-Muconic Acid Production via New Metabolic Designs Corresponding to the Heterogeneity of Lignin

Cited by 122 publications

References 38 publications

Exploring the Selective Demethylation of Aryl Methyl Ethers with a Pseudomonas Rieske Monooxygenase

Exploring the Selective Demethylation of Aryl Methyl Ethers with a Pseudomonas Rieske Monooxygenase

Strategies for the production of biochemicals in bioenergy crops

High value‐added monomer chemicals and functional bio‐based materials derived from polymeric components of lignocellulose by organosolv fractionation

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