Masaya Nakamura

Forestry and Forest Products Research Institute, Tsukuba, Ibaraki, Japan

Are you Masaya Nakamura?

Claim your profile

Publications (52)

  • Yuichiro Otsuka · Motoki Matsuda · Tomonori Sonoki · [...] · Masaya Nakamura
    [Show abstract] [Hide abstract] ABSTRACT: This study characterized the enzymatic ability of a cell-free extract from an acidophilic (+)-catechin degrader Burkholderia oxyphila (OX-01). The crude OX-01 extracts were able to transform (+)-catechin and (−)-epicatechin into (+)-taxifolin via a leucocyanidin intermediate in a two-step oxidation. Enzymatic oxidation at the C-4 position was carried out anaerobically using H2O as an oxygen donor. The C-4 oxidation occurred only in the presence of the 2R-catechin stereoisomer, with the C-3 stereoisomer not affecting the reaction. These results suggest that the OX-01 may have evolved to target both (+)-catechin and (−)-epicatechin, which are major structural units in plants.
    Article · Aug 2016 · Bioscience Biotechnology and Biochemistry
  • Article · May 2016 · Bioresources
  • [Show abstract] [Hide abstract] ABSTRACT: 2-Pyrone-4,6-dicarboxylic acid (PDC), a chemically stable metabolic intermediate of lignin, showed preferential Cs+ sedimentation even from the aqueous solutions containing other alkali metal ions, such as Na+. From the crystal structure of the Cs+/PDC complex, Cs+ was revealed to be coordinated by 10 oxygen atoms of PDC and such multiple coordination was the reason of the preferential complex formation of Cs+ with PDC.
    Article · Mar 2016 · Journal of Nuclear Science and Technology
  • Article · Jan 2016 · Green Chemistry
  • [Show abstract] [Hide abstract] ABSTRACT: In this work, the effects of PcaJ (beta-ketoadipate:succinyl-coenzyme A transferase)- and PcaD (beta-ketoadipate enol-lactone hydrolase)-inactivation on protocatechuic acid metabolism in Pseudomonas putida KT2440 were evaluated. Beta-ketoadipic acid was produced from protocatechuic acid by the inactivation of PcaJ as expected; however, a portion of the produced beta-ketoadipic acid was converted to levulinic acid through a purification step consisting of extraction from the culture and recrystallization. On the other hand, muconolactone was purified from the culture of the PcaD-inactivated mutant of KT2440, although beta-ketoadipate enol-lactone was supposed to be produced because it is the substrate of PcaD. Under aerobic conditions, it has been reported that lignin-related aromatics are metabolized through PCA 2,3- or 3,4- or 4,5-ring cleavage pathways, and muconolactone is an intermediate observed in the metabolism of catechol, not protocatechuic acid. Our results will provide a prospective route to produce muconolactone with a high yield through the protocatechuate-3,4-metabolic pathway.
    Article · Dec 2015 · Journal of Bioscience and Bioengineering
  • Source
    Full-text Dataset · Nov 2015
  • Source
    [Show abstract] [Hide abstract] ABSTRACT: Biochemical production processes require water and nutrient resources for culture media preparation, but aqueous waste is generated after the target products are extracted. In this study, culture waste (including cells) produced from a lab-scale fermenter was fed into a microbial fuel cell-membrane bioreactor (MFC-MBR) system. Electrical energy was generated via the interaction between the microbial consortia and the solid electrode in the MFC. The treated wastewater was reclaimed in this process which was reused as a solvent and a nutrient source in subsequent fermentation. Polarization testing showed that the MFC produced a maximum current density of 37.53 A m(-3) with a maximum power density of 5.49 W m(-3). The MFC was able to generate 0.04 kWh of energy per cubic meter of culture waste treated. The lab-scale fermenters containing pure cultures of an engineered Pseudomonas spp. were used to generate 2-pyrone-4,6-dicarboxylic acid (PDC), a high value platform chemical. When the MFC-MBR-treated wastewater was used for the fermenter culture medium, a specific bacterial growth rate of 1.00 ± 0.05 h(-1) was obtained with a PDC production rate of 708.11 ± 64.70 mg PDC L(-1) h(-1). Comparable values for controls using pure water were 0.95 ± 0.06 h(-1) and 621.01 ± 22.09 mg PDC L(-1) h(-1) (P > 0.05), respectively. The results provide insight on a new approach for more sustainable bio-material production while at the same time generating energy, and suggest that the treated wastewater can be used as a solvent and a nutrient source for the fermentation production of high value platform chemicals.
    Full-text Article · May 2015 · Bioprocess and Biosystems Engineering
  • [Show abstract] [Hide abstract] ABSTRACT: The decarboxylation reaction of protocatechuate has been described as a bottleneck and a rate-limiting step in cis,cis-muconate (ccMA) bioproduction from renewable feedstocks such as sugar. Because sugars are already in high demand in the development of many bio-based products, our work focuses on improving protocatechuate decarboxylase (Pdc) activity and ccMA production in particular, from lignin-related aromatic compounds. We previously had transformed an Escherichia coli strain using aroY, which had been used as a protocatechuate decarboxylase encoding gene from Klebsiella pneumoniae subsp. pneumoniae A170-40, and inserted other required genes from Pseudomonas putida KT2440, to allow the production of ccMA from vanillin. This recombinant strain produced ccMA from vanillin, however the Pdc reaction step remained a bottleneck during incubation. In the current study, we identify a way to increase protocatechuate decarboxylase activity in E. coli through enzyme production involving both aroY and kpdB; the latter which encodes for the B subunit of 4-hydroxybenzoate decarboxylase. This permits expression of Pdc activity at a level approximately 14-fold greater than the strain with aroY only. The expression level of AroY increased, apparently as a function of the co-expression of AroY and KpdB. Our results also imply that ccMA may inhibit vanillate demethylation, a reaction step that is rate limiting for efficient ccMA production from lignin-related aromatic compounds, so even though ccMA production may be enhanced, other challenges to overcome vanilate demethylation inhibition still remain.
    Article · Oct 2014 · Journal of Biotechnology
  • [Show abstract] [Hide abstract] ABSTRACT: Sphingobium sp. strain SYK-6 is able to assimilate lignin-derived biaryls, including a biphenyl compound, 5,5'-dehydrodivanillate (DDVA). Previously, ligXa (SLG_07770), which is similar to oxygenase components of Rieske-type non-heme iron aromatic ring-hydroxylating oxygenases, was identified to be essential for the conversion of DDVA; however, the genes encoding electron transfer components remained unknown. Disruption of putative electron transfer component genes scattered through the SYK-6 genome indicated that SLG_08500 and SLG_21200, which showed approximately 60% amino acid sequence identities with ferredoxin and ferredoxin reductase of dicamba O-demethylase, were essential for the normal growth of SYK-6 on DDVA. LigXa and the gene products of SLG_08500 (LigXc) and SLG_21200 (LigXd) were purified and were estimated to be a trimer, a monomer, and a monomer. LigXd contains FAD as the prosthetic group, and showed much higher reductase activity toward 2,6-dichlorophenolindophenol with NADH than NADPH. A mixture of purified LigXa, LigXc, and LigXd converted DDVA into 2,2',3-trihydroxy-3'-methoxy-5,5'-dicarboxybiphenyl in the presence of NADH, indicating that DDVA O-demethylase is a three-component monooxygenase. This enzyme requires Fe(II) for its activity and is highly specific for DDVA with the Km value of 63.5 μM and kcat of 6.1 sec(-1). Genome searches in six other sphingomonads revealed genes similar to ligXc and ligXd (>58% amino acid sequence identities) with a limited number of electron transfer component genes, yet a diverse number of oxygenase component genes were found. This fact implies that these few electron transfer components are able to interact with numerous oxygenase components, and the conserved LigXc and LigXd orthologs are important in sphingomonads.
    Article · Sep 2014 · Applied and Environmental Microbiology
  • [Show abstract] [Hide abstract] ABSTRACT: Cycloaddition reactions of a lignin-derived pyrone derivative, 2-pyrone-4,6-dicarboxylic acid and its dimethyl ester with alkenyl acetates and alkynes under thermal conditions proceed with decarboxylation to give isophthalic acids and various mono- and disubstituted isophthalates. A ruthenium complex catalyzes the reaction with alkynes under milder conditions and affords products with different regioselectivity from that observed under thermal conditions.
    Article · Aug 2014 · Chemistry Letters
  • Source
    [Show abstract] [Hide abstract] ABSTRACT: Subcritical water extraction of low-molecular-weight phenolic compounds from oil palm biomass (trunk, bark, petiole, rachis, leaves, empty fruit bunch fiber, midrib spine leaflets, stalk of fruit bunches, flesh, kernel shells, and albumen) was conducted. It was elucidated that gallic acid, protocatechuicaldehyde, p-hydroxybenzoic acid, p-hydroxybenzaldehyde, vanillic acid, syringic acid, vanillin, syringaldehyde p-coumaric acid and ferulic acid, all of which could be used as 2-pyrone-4,6-dicarboxylic acid (PDC) precursors, were contained in all parts of oil palm, although their composition differed. The peak yield of p-hydroxybenzoic acid was obtained among the PDC precursors. With regard to extraction conditions, temperature: 200°C, time: 20-60 min, and liquor ratio: 50-125 were the most efficient. The kernel shell exhibited the highest yield of PDC precursors, followed by the trunk, empty fruit bunch fiber, and bark. The results of our study indicate the oil palm is a potentially valuable source of PDC precursors.
    Full-text Article · Jul 2014 · Japan Agricultural Research Quarterly
  • [Show abstract] [Hide abstract] ABSTRACT: Thermoplasticization of lignin was achieved by the acylation of polyfunctional lignin yielded in the course of the alkali cooking of wood tips. The kneading of acylated lignin and poly(e-caprolactone) gave the composite film with reasonable flexibility and light blocking property which might provide several utilization ways of lignin to serve as substitution of petroleum products. The un-acylated (virgin) lignin also gave flexible, thermoplastic composites with polypropylene (PP) when maleate-modified PP co-existed.
    Article · May 2013 · FIBER
  • [Show abstract] [Hide abstract] ABSTRACT: 2-Pyrone-4,6-dicarboxylic acid (PDC), a chemically stable metabolic intermediate of lignin, was converted into the corresponding acid chloride and thermoplastic polyesters were synthesized by polycondensation with several aromatic diols. The polyesters exhibited high decomposition temperature due to the presence of aromatic group adjacent to the PDC group. The films prepared by hot-pressing gave relatively high fracture stress that is almost comparable to poly(ethylene terephthalate) (PET) and showed oriented crystallization upon stretching.
    Article · Jan 2013 · FIBER
  • Yuzo Suzuki · Masaya Nakamura · Yuichiro Otsuka · [...] · Yoshihiro Katayama
    [Show abstract] [Hide abstract] ABSTRACT: The degradation of 2-chloro-4,5-O-(4'-methyl-7', 8'-diphenyl)ether (CMDPE), an analog of 2,7-dichlorodibenzo-p-dioxin (2,7-DCDD), mediated by Geobacillus sp. UZO 3 cell-free extract was monitored. Ethyl acetate extracts of a complete reaction mixture incubated at 65°C for 18 h were analyzed either by thin layer chromatography (TLC) fractionation coupled with spectrometric detection or by gas chromatography-mass spectrometry (GC-MS). The reaction product 4-methylumbelliferone (4MU) was successfully isolated by TLC and visualized by a transilluminator at 450 nm. The 4MU, 4-chlorophenol, and reaction intermediate 6-chlorophenoxy-4-methylumbelliferone were all successfully detected by GC-MS. The presence of these compounds suggest that Geobacillus sp. UZO 3 cell-free extract also catalyzes the reductive cleavage of the diaryl ether bonds of CMDPE in a similar mechanism previously reported in 2,7-DCDD. In the present study, the authors describe a simple and highly sensitive fluorescent assay for a new dioxin degrading enzyme(s).
    Article · May 2012 · Environmental Toxicology and Chemistry
  • [Show abstract] [Hide abstract] ABSTRACT: The gene encoding manganese peroxidase of a white-rot fungus Phanerochaete crassa WD1694 was cloned and sequenced. Four genomic clones were sequenced in which 3 clones were existed as alleles. The analysis of intron–exon structures divided the 4 clones into three subfamilies that corresponded to mnp2 and mnp3 of Phanerochaete chrysosporium, and a new subfamily possessing only five introns. The purified P. crassa WD1694 MnP consisted of 4 isozymes with same molecular weight, same N-terminal sequence, and different pI. N-terminal sequence of deduced protein of P. crassa mnpB3 gene was identical to those of 4 MnP isozymes; however, the other 3 mnp genes had different N-terminal sequence. The molecular weight of encoded mature protein of mnpB3 gene and purified MnP had a gap that could be difference between MnP proteins encoded by single gene. The results suggested that 4 MnP isozymes of P. crassa WD1694 arose from single gene.
    Article · Apr 2012 · Journal of Wood Science
  • [Show abstract] [Hide abstract] ABSTRACT: Export Date: 23 April 2013, 情報源: Scopus
    Article · Apr 2012 · FIBER
  • Shojiro Hishiyama · Yuichiro Otsuka · Masaya Nakamura · [...] · Yoshihiro Katayama
    [Show abstract] [Hide abstract] ABSTRACT: Guaiacylglycerol-beta-guaiacyl ether (GGE) is one of the most important phenolic compound for studying the chemistry and biochemistry of lignin. GGE contains two asymmetric carbons at the alpha and beta positions of its side chain: therefore, theoretically it can exist as four different stereoisomers. It has been proposed that a Gram-negative bacterium, Sphingobium sp. SYK-6 (formerly referred as Sphingomonas paucimobilis SYK-6), degrades GGE enantiospecifically via cleavage of the ether bond. The cleavage was thought to proceed in two steps, each catalyzed by a different enantiospecific enzyme. In the first step, the alcohol residue at the alpha position of the side chain in GGE was thought to be oxidized enantiospecifically by four distinct C alpha-dehydrogenases (LigD, LigN, LigL and LigO), to produce two enantiomers of 3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-2-(2-methoxyphenoxy)-propan-1-one (erone). To study this enantiospecific degradation step by the four dehydrogenases, we synthesized all four stereoisomers of GGE and both enantiomers of erone and separated them into enantiopure samples. The stereoisomers and our synthetic methods to prepare them are useful both for microbial and chemical investigations of lignin degradation.
    Article · Feb 2012 · Tetrahedron Letters
  • [Show abstract] [Hide abstract] ABSTRACT: The glutathione S-transferases, LigF and LigE, of Sphingobium sp. strain SYK-6 respectively play a role in cleavage of the beta-aryl ether of (+)-(beta S)-alpha-(2-methoxyphenoxy)-beta-hydroxypropiovanillone (MPHPV) and (-)(-beta R)-MPHPV. The ligP gene, which showed 59% similarity to ligE at the amino acid level, was isolated from SYK-6. LigP produced in Escherichia coli revealed enantioselectivity for (-)-(beta R)-MPHPV, and ligE and ligP alone contributed to the degradation of (-)-(beta R)-MPHPV in SYK-6.
    Article · Dec 2011 · Bioscience Biotechnology and Biochemistry
  • [Show abstract] [Hide abstract] ABSTRACT: Two cholesterol groups were for the first time attached to a lignin-derived metabolic intermediate, 2-pyrone-4,6-dicarboxylic acid (PDC). This PDC molecule showed a liquid crystalline mesophase and interesting organogelation behavior. The relationship between molecular structure and assembly properties was investigated by modifying the PDC core and a spacer group between the PDC and cholesterol moieties. Although all derivatives displayed similar phase transition behavior with a SmA phase, only a few of them could form organogels. Detailed morphology investigations of the xerogels by X-ray diffraction (XRD) and scanning electron microscopy (SEM) suggested that both the PDC moiety and a carbamate spacer are essential for the occurrence of organogelation. Hydrogen bonds of the carbamate spacers and van der Waals interactions of the cholesterol moieties lead to a dipolar-induced interaction of the pyrone rings. The physical gels were probably stabilized by these cooperative interactions. The IR and H-1 NMR spectroscopies clearly revealed the presence of weak intermolecular interactions, such as hydrogen bonds and dipolar-type interactions, for efficient gelator molecules.
    Article · Jun 2011 · Bulletin of the Chemical Society of Japan
  • [Show abstract] [Hide abstract] ABSTRACT: Novel biomass-based polymers composed of 2-pyrone-4,6-dicarboxylic acid (PDC), which was isolated from lignin as a chemically stable metabolic intermediate, were synthesized by the copper (Cu) (I)-catalyzed, but ligand-free azide-alkyne cycloaddition reaction. The polymerization progress was monitored by the gel permeation chromatography profiles and IR spectroscopies. Very high-molecular-weight polymers with sufficient solubilities in organic solvents were obtained after the polymerization for 70 h, and their chemical structures were fully characterized. The in-situ prepared PDC polymers displayed adhesive properties to various metal surfaces. Among the investigated metals, the tensile strength with Cu, prepared at 70 °C for 4 h, was the highest (3.70 MPa). This specific adhesion to Cu is probably due to the promoted polymerization using the leached CuI as a catalyst and the crosslinking ability through the interactions with the formed triazole rings. © The Society of Polymer Science, Japan (SPSJ) All rights reserved.
    Article · May 2011 · Polymer Journal