Tenacious Epoxy Adhesives Prepared from Lignin-derived Stable Metabolic Intermediate

Hasegawa, Yuki; Shikinaka, Kazuhiro; Katayama, Yoshihiro; Kajita, Shinya; Masai, Eiji; Nakamura, Masaya; Otsuka, Yuichiro; Ohara, Seiji; Shigehara, Kiyotaka

doi:10.2115/fiber.65.359

Cited by 28 publications

(23 citation statements)

References 15 publications

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“…Our research group has discovered that 2-pyrone-4,6-dicarboxylic acid (PDC), an intermediate of the PCA45 pathway (Fig. 1A), is useful in the production of biodegradable and high-functional polymers, such as strong adhesives (15,16,30). The production of PDC via the PCA45 pathway from lignin-derived compounds and petrochemical aromatic compounds, including phthalates, would be worthwhile for reducing the environmental load.…”

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confidence: 99%

Characterization of the Protocatechuate 4,5-Cleavage Pathway Operon in Comamonas sp. Strain E6 and Discovery of a Novel Pathway Gene

Kamimura

Aoyama

Yoshida

et al. 2010

Appl Environ Microbiol

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The protocatechuate (PCA) 4,5-cleavage (PCA45) pathway is the essential catabolic route for the degradation of various aromatic acids in the genus Comamonas. All of the PCA45 pathway genes, orf1-pmdKEFDABC, as well as another PCA 4,5-dioxygenase gene, pmdA II B II , were isolated from a phthalate-degrading bacterium, Comamonas sp. strain E6. Disruption of pmdB and pmdD in E6, which code for the ␤ subunit of PCA 4,5-dioxygenase and 2-pyrone-4,6-dicarboxylate (PDC) hydrolase, respectively, resulted in a growth defect on PCA, indicating that these genes are essential for the growth of E6 on PCA. On the other hand, inactivation of pmdB II did not affect the growth of E6 on PCA. Disruption of pmdK, which is related to a 4-hydroxybenzoate/ PCA transporter of Pseudomonas putida, resulted in growth retardation on PCA. The insertional inactivation of orf1 in E6, whose deduced amino acid sequence has no similarity with proteins of known function, led to the complete loss of growth on PCA and the accumulation of PDC and 4-oxalomesaconate (OMA) from PCA. These results indicated the involvement of orf1 in the PCA45 pathway, and this gene, designated pmdU, was suggested to code for OMA tautomerase. Reverse transcription-PCR analysis suggested that the pmdUKEFDABC genes constitute an operon. The transcription start site of the pmd operon was mapped at 167 nucleotides upstream of the initiation codon of pmdU. The pmd promoter activity was enhanced 20-fold when the cells were grown in the presence of PCA. Inducers of the pmd operon were found to be PCA and PDC, but PDC was the more effective inducer.Protocatechuate (PCA) is a key intermediate metabolite in the bacterial degradation pathways of various aromatic compounds, including phthalate isomers, vanillate, and hydroxybenzoates. It is known that PCA is degraded via three distinct catabolic pathways, including the PCA 2,3-cleavage (8, 18), PCA 3,4-cleavage (14), and PCA 4,5-cleavage (PCA45) (19,26,27) pathways. Our research group has discovered that 2-pyrone-4,6-dicarboxylic acid (PDC), an intermediate of the PCA45 pathway (Fig. 1A), is useful in the production of biodegradable and high-functional polymers, such as strong adhesives (15,16,30). The production of PDC via the PCA45 pathway from lignin-derived compounds and petrochemical aromatic compounds, including phthalates, would be worthwhile for reducing the environmental load. From this aspect, the catabolic functions of Comamonas sp. strain E6, which is able to utilize phthalate isomers as sole carbon and energy sources via the PCA45 pathway (11, 38), appears to be of importance.The PCA45 pathway was first enzymatically characterized by Kersten et al. (19) and . In this pathway (Fig. 1A), PCA is initially transformed to 4-carboxy-2-hydroxymuconate-6-semialdehyde (CHMS) by PCA 4,5-dioxygenase (4,5-PCD). CHMS is nonenzymatically converted to an intramolecular hemiacetal form and then oxidized by CHMS dehydrogenase. The resulting intermediate, PDC, is hydrolyzed by PDC hydrolase to yield the keto and enol tautomers of 4-oxa...

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confidence: 99%

Characterization of the Protocatechuate 4,5-Cleavage Pathway Operon in Comamonas sp. Strain E6 and Discovery of a Novel Pathway Gene

Kamimura

Aoyama

Yoshida

et al. 2010

Appl Environ Microbiol

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“…13 73 . These results show that the novel epoxy adhesive containing diglycidyl PDC exhibits a higher tensile strength than that of common petroleum-based epoxy adhesives such as the diglycidyl ester of bisphenol-A 74 . Conversion of the carboxylic groups in PDC into cholesteryl groups gives a PDC-based organogelator 75,76 .…”

Section: Utilization Of Pdc As Functional Monomermentioning

confidence: 76%

Utilization of Lignocellulosic Biomass via Novel Sustainable Process

et al. 2018

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“…The application of PDC to epoxy resin is also studied as well as the polymers based on PDC. The following two kinds of methods are proposed for the preparation of the PDC‐based epoxy resin in the work [64] and the patent, JP‐A No. 2010‐59095; one is the method of performing the epoxidation with glycidol at low temperature (0–5°C) in tetrahydrofuran, and the other is that of performing the dehydration of PDC with nonsaturation alcohol such as allyl alcohol in the presence of an acid catalyst, followed by oxidizing the terminal double bonds.…”

Section: Wood‐based Epoxy Resin Systemsmentioning

confidence: 99%

Progress in development of epoxy resin systems based on wood biomass in Japan

Koike¹

2012

Polymer Engineering & Sci

117

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This article reviews the progress in the development of wood biomass origin epoxy resin system from 1960s to recent years in Japan. The methods of using wood biomass for epoxy resin systems are classified into the following three categories; one is the method of preparing lignin‐epoxy resins after applying treatments on the industrial lignin, which has been disposed in large volume, another is that of using wood as the raw material of epoxy resin system after applying treatments directly on wood, and the other is that of composing epoxy resin and/or curing agent from woody raw materials (except the industrial lignin), which are isolated and refined from wood before the treatments. Although several promising technologies have been developed and tried to be industrialized in Japan, the full‐fledged development of wood biomass‐based epoxy resin has just started when viewed as a whole. These developments will be further accelerated toward the construction of the environment harmony type and the resources circulation type societies. As the result of continuous developmental efforts, it is expected that we can look at the scene where epoxy resins are sustainably supplied in various forms even after the depletion of oil resources. POLYM. ENG. SCI.,, 2012. © 2012 Society of Plastics Engineers

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Tenacious Epoxy Adhesives Prepared from Lignin-derived Stable Metabolic Intermediate

Cited by 28 publications

References 15 publications

Characterization of the Protocatechuate 4,5-Cleavage Pathway Operon in Comamonas sp. Strain E6 and Discovery of a Novel Pathway Gene

Characterization of the Protocatechuate 4,5-Cleavage Pathway Operon in Comamonas sp. Strain E6 and Discovery of a Novel Pathway Gene

Utilization of Lignocellulosic Biomass via Novel Sustainable Process

Progress in development of epoxy resin systems based on wood biomass in Japan

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