WO2023120538A1 - Procédé de production d'acide 4-hydroxybenzoïque - Google Patents
Procédé de production d'acide 4-hydroxybenzoïque Download PDFInfo
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- WO2023120538A1 WO2023120538A1 PCT/JP2022/046954 JP2022046954W WO2023120538A1 WO 2023120538 A1 WO2023120538 A1 WO 2023120538A1 JP 2022046954 W JP2022046954 W JP 2022046954W WO 2023120538 A1 WO2023120538 A1 WO 2023120538A1
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- acid
- poba
- aqueous solution
- bacterium
- bacteria
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- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 title claims abstract description 147
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- 238000010361 transduction Methods 0.000 description 1
- 230000026683 transduction Effects 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
- C12N15/00—Mutation or genetic engineering; DNA or RNA concerning genetic engineering, vectors, e.g. plasmids, or their isolation, preparation or purification; Use of hosts therefor
- C12N15/09—Recombinant DNA-technology
- C12N15/63—Introduction of foreign genetic material using vectors; Vectors; Use of hosts therefor; Regulation of expression
- C12N15/74—Vectors or expression systems specially adapted for prokaryotic hosts other than E. coli, e.g. Lactobacillus, Micromonospora
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/40—Preparation of oxygen-containing organic compounds containing a carboxyl group including Peroxycarboxylic acids
- C12P7/42—Hydroxy-carboxylic acids
Definitions
- the present invention includes the following [1] to [6].
- a method for producing 4-hydroxybenzoic acid comprising the following steps (1) and (2).
- Step (1) Preparing an aqueous solution containing coumaric acid and ferulic acid
- Step (2) Bacteria deficient in PobA enzyme expression are allowed to act on the aqueous solution prepared in Step (1), and the bacteria produce ferulic acid. as a growth carbon source, and converting the coumaric acid to 4-hydroxybenzoic acid by the bacteria
- the step (1) includes alkali-treating the lignin-containing biomass to contain coumaric acid and ferulic acid.
- [3] The method for producing 4-hydroxybenzoic acid according to [1] or [2], wherein the aqueous solution prepared in step (1) has a sugar concentration of less than 5 g/L.
- ferulic acid and coumaric acid are sometimes covalently bound to polysaccharides in the solid raw materials, in order to increase the extraction efficiency, a hydrolysis reaction is performed in a high-temperature alkaline aqueous solution for several hours to obtain ferulic acid. and coumaric acid are preferably eluted in an alkaline aqueous solution.
- the solid raw material for obtaining the extract is preferably lignin-containing biomass.
- Lignin-containing biomass refers to biological resources that contain at least lignin components. Specific examples of lignin-containing biomass include herbaceous biomass such as bagasse, corn cob, switchgrass, napier grass, erianthus, corn stover, rice straw, and straw; woody biomass such as trees and waste building materials; biomass derived from aquatic environments such as algae and seaweed; grain husk biomass such as corn husks, wheat husks, soybean husks and rice husks.
- step (1) is a step of treating lignin-containing biomass with alkali to obtain an extract containing coumaric acid and ferulic acid as the aqueous solution.
- the aqueous solution prepared in step (1) may contain sugar, and the sugar concentration in that case is preferably less than 5 g/L, more preferably 1 g/L or less.
- the lower limit of the sugar concentration of the aqueous solution prepared in step (1) is zero.
- the sugar concentration of the aqueous solution prepared in step (1) is 5 g/L or more, the 4HBA production rate and the 4HBA yield from coumaric acid decrease. This is because the bacterium of the present invention preferentially consumes sugar as a carbon source.
- a Pseudomonas bacterium in which the PobA enzyme is functionally inactivated is, for example, a Pseudomonas bacterium (for example, a wild-type bacterium) before deficient expression of the PobA enzyme, in which the activity of the PobA enzyme is reduced or eliminated.
- Known methods for deficient expression of the PobA enzyme in target bacteria include methods of disrupting the pobA gene by homologous recombination.
- methods such as introduction of mutations into the pobA gene and inactivation of the pobA gene are also known.
- Genetic manipulations such as phage transduction, homologous recombination, plasmid vector insertion, and the like can be used to abolish PobA enzyme expression in the bacterium of interest.
- Methods using homologous recombination include gene knockout for gene disruption and gene knockin for mutation introduction.
- a method of disrupting the pobA gene of a wild-type bacterium by homologous recombination is used as a method of deficient PobA enzyme expression in a target bacterium.
- Disruption of the pobA gene may be insertion of a disruption cassette into the pobA gene by homologous recombination, replacement of the pobA gene with the disruption cassette by homologous recombination, or pobA gene by homologous recombination.
- Table 1 shows the component composition of the bagasse alkali extract.
- Pseudomonas putida (P. putida) strain KT2440 was inoculated into 10 mL of LB liquid medium and cultured with shaking at 30° C. for 16 hours. A portion of the culture was inoculated into 5 mL of fresh LB liquid medium and cultured with shaking at 30° C. until OD 600 reached 0.3-0.5. Cells were collected from the resulting culture medium by centrifugation (6,000 ⁇ g, 5 min, 4° C.) and washed with a cooled 10% Glycerol solution. The washing operation was repeated 3 times. The washed cells were collected by centrifugation and suspended in 0.1 mL of chilled 10% Glycerol solution.
- Example 3 Preculture of Pseudomonas bacterium (KT2440 strain ⁇ PobA strain) deficient in PobA enzyme expression KT2440 strain ⁇ PobA strain was statically cultured overnight at 30°C on an LB agar medium. A colony formed on the agar medium was inoculated into 10 mL of an LB liquid medium and cultured with shaking at 30° C. for 16 hours. 1 mL of a cell suspension (suspended in physiological saline) having an OD 600 of 5.0 was prepared from the obtained culture medium and used as an inoculum.
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- Genetics & Genomics (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Biotechnology (AREA)
- General Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Microbiology (AREA)
- General Health & Medical Sciences (AREA)
- Biomedical Technology (AREA)
- Biochemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Physics & Mathematics (AREA)
- Biophysics (AREA)
- Molecular Biology (AREA)
- Plant Pathology (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Abstract
La présente invention a pour but de procurer un procédé de production à haut rendement d'acide 4-hydroxybenzoïque (4HBA) à partir d'un matériau de départ tel qu'une biomasse, et fournit un procédé de production d'acide 4-hydroxybenzoïque comprenant les étapes (1) et (2) suivantes. Étape (1) : préparation d'une solution aqueuse contenant de l'acide coumarique et de l'acide férulique ; et étape (2) : action d'une bactérie présentant un défaut d'expression de l'enzyme PobA sur la solution aqueuse préparée à l'étape (1) pour métaboliser l'acide férulique comme source de carbone de croissance par la bactérie et conversion de l'acide coumarique en acide 4-hydroxybenzoïque par la bactérie.
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Citations (2)
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JP2016526896A (ja) * | 2013-07-22 | 2016-09-08 | ビーエーエスエフ ソシエタス・ヨーロピアBasf Se | フェルラ酸からのバニリンの迅速かつ高収率な製造のためのシュードモナス・プチダkt2440の遺伝子操作 |
WO2017170549A1 (fr) * | 2016-03-29 | 2017-10-05 | 東レ株式会社 | Procédé de production d'acide hydroxycinnamique |
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2022
- 2022-12-20 JP JP2023512010A patent/JPWO2023120538A1/ja active Pending
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JP2016526896A (ja) * | 2013-07-22 | 2016-09-08 | ビーエーエスエフ ソシエタス・ヨーロピアBasf Se | フェルラ酸からのバニリンの迅速かつ高収率な製造のためのシュードモナス・プチダkt2440の遺伝子操作 |
WO2017170549A1 (fr) * | 2016-03-29 | 2017-10-05 | 東レ株式会社 | Procédé de production d'acide hydroxycinnamique |
Non-Patent Citations (8)
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AKUTSU, MIHO; KAMIMURA, NAOHUMI; MASAI, EIJI; SONOKI, TOMONORI: "2A16a13 Application of Pseudomonas sp. NGC7 to the production of 4-hydroxybenzoic acid from lignin", ANNUAL MEETING OF JAPAN SOCIETY FOR BIOSCIENCE, BIOTECHNOLOGY, AND AGROCHEMISTRY (JSBBA2020); MARCH 25 - 28, 2020, vol. 2020, 1 January 2020 (2020-01-01) - 28 March 2020 (2020-03-28), pages 272, XP009547239 * |
CHRISTOPHER W. JOHNSON, ET AL.: "Enhancing muconic acid production from glucose and lignin-derived aromatic compounds via increased protocatechuate decarboxylase activity", METABOLIC ENGINEERING COMMUNICATIONS, ELSEVIER, NL, vol. 3, 1 December 2016 (2016-12-01), NL , pages 111 - 119, XP055537131, ISSN: 2214-0301, DOI: 10.1016/j.meteno.2016.04.002 * |
KARLEN STEVEN D., FASAHATI PEYMAN, MAZAHERI MONA, SERATE JOSE, SMITH REBECCA A., SIROBHUSHANAM SIRISHA, CHEN MINGJIE, TYMOKHIN VIT: "Assessing the Viability of Recovery of Hydroxycinnamic Acids from Lignocellulosic Biorefinery Alkaline Pretreatment Waste Streams", CHEMSUSCHEM, WILEY-VCH, DE, vol. 13, no. 8, 21 April 2020 (2020-04-21), DE , pages 2012 - 2024, XP093074000, ISSN: 1864-5631, DOI: 10.1002/cssc.201903345 * |
NONAKA KAZUHIRO, OHTA HIROYUKI, SATO YOSHINORI, HOSOKAWA KEIICHI: "Utilization of Phenylpropanoids by Pseudomonas putida Soil Isolates and Its Probable Taxonomic Significance", MICROBES AND ENVIRONMENTS, vol. 23, no. 4, 1 January 2008 (2008-01-01), pages 360 - 364, XP093073993, ISSN: 1342-6311, DOI: 10.1264/jsme2.ME08545 * |
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WANG WEI, CHEN XIAOWEN, KATAHIRA RUI, TUCKER MELVIN: "Characterization and Deconstruction of Oligosaccharides in Black Liquor From Deacetylation Process of Corn Stover", FRONTIERS IN ENERGY RESEARCH, vol. 7, XP093073997, DOI: 10.3389/fenrg.2019.00054 * |
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