WO2017099209A1 - 3-オキソアジピン酸の製造方法 - Google Patents
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Definitions
- the present invention relates to a method for producing 3-oxoadipic acid using microorganisms.
- 3-Oxoadipic acid (also known as ⁇ -ketoadipic acid, IUPAC name: 3-oxohexaneic acid) is a dicarboxylic acid having 6 carbon atoms and a molecular weight of 160.12.
- 3-Oxoadipic acid can be used as a polyester by polymerizing with a polyhydric alcohol and as a raw material for polyamide by polymerizing with a polyvalent amine.
- ammonia to the terminal of 3-oxoadipic acid to make lactam, it can be used alone as a raw material for polyamide.
- 3-Oxoadipic acid is produced in the process in which microorganisms such as soil bacteria and fungi enzymatically degrade aromatic compounds such as catechol and protocatechuic acid into compounds with fewer carbon atoms.
- This degradation pathway is generally known as the ⁇ -ketoadipate pathway.
- Patent Document 1 discloses a method for fermentative production of 3-oxoadipic acid using vanillic acid and / or protocatechuic acid, which is an aromatic compound that can be generated by the decomposition of lignin, but using an aliphatic compound as a raw material. There is no disclosure of fermentative production of 3-oxoadipic acid. In general, a wide variety of aromatic compounds are mixed in a lignin decomposition product obtained by chemical decomposition. When producing 3-oxoadipic acid from a lignin decomposition product as a raw material, vanillic acid and / or Alternatively, a large amount of components other than protocatechuic acid that cannot be metabolized by microorganisms remain in the culture solution. Therefore, not only is it difficult to separate 3-oxoadipic acid, but also the problem is low utilization efficiency of raw materials.
- Patent Document 2 describes that 3-oxoadipic acid (3-oxoadipate) can be produced as an intermediate of the target adipic acid in a microorganism artificially improved so that adipic acid can be produced.
- 3-oxoadipic acid can actually be produced using the metabolic pathway of microorganisms.
- succinyl-CoA and acetyl-CoA are used as starting materials. It was not clear whether 3-oxoadipic acid could be produced as a raw material.
- an object of the present invention is to provide a method for producing 3-oxoadipic acid from an aliphatic compound that can be easily used by microorganisms such as sugars by utilizing the metabolic pathway of the microorganisms.
- the present invention provides the following (1) to (29).
- Serratia genus microorganism, Corynebacterium genus microorganism, Hafnia genus microorganism, Bacillus genus microorganism, Escherichia genus microorganism, Pseudomonas genus microorganism, Alcaligenes genus microorganism, Shimwellia genus microorganism, Nocilia genus microorganism microorganism , Microorganisms belonging to the genus Cupriavidus, microorganisms belonging to the genus Rhodosporidium, microorganisms belonging to the genus Streptomyces, microorganisms belonging to the genus Microbacteria, microorganisms belonging to the genus Planomicrobium, microorganisms belonging to the genus Rhodosporium, microorganisms belonging to the genus Saccharomyces Made is selected from the group, comprising culturing at least
- Culturing at least one microorganism having the ability to produce 3-oxoadipic acid selected from the group consisting of a microorganism belonging to the genus Cupriavidus, a microorganism belonging to the genus Rhodosporidium, a microorganism belonging to the genus Streptomyces, a microorganism belonging to the genus Planomicrobium, and a microorganism belonging to the genus Rhodosporium.
- the Serratia genus microorganism is Serratia plymuthica, Serratia grimesii, Serratia ficaria, Serratia fonticola, Serratia odorifera, Serratia entomophila, or 1 method.
- the Corynebacterium genus microorganism is Corynebacterium glutamicum, Corynebacterium acetoacidophilum, Corynebacterium acetoglutamicum or Corynebacterium ammonianes (Method 1 or 2).
- the Pseudomonas genus microorganism is Pseudomonas putida, Pseudomonas fraggi, Pseudomonas fluorescens, Pseudomonas reptilivoras, or Pseudomonas azotoform (2) or Pseudomonas azotoforma (Method 2).
- 3-oxoadipic acid can be obtained by utilizing the metabolic pathway of microorganisms.
- the method for producing 3-oxoadipic acid according to the present invention includes a step of culturing a microorganism capable of producing 3-oxoadipic acid. More specifically, the method is characterized in that 3-oxoadipic acid is produced by culturing a microorganism capable of producing 3-oxoadipic acid by utilizing the metabolic pathway of the microorganism.
- the microorganism having the ability to produce 3-oxoadipic acid used in the method of the present invention is selected from the following microorganisms.
- Serratia microorganisms ⁇ Corynebacterium microorganisms ⁇ Pseudomonas microorganisms ⁇ Bacillus microorganisms ⁇ Hafnia microorganisms ⁇ Escherichia microorganisms ⁇ Acinetobacter microorganisms ⁇ Alcaligenes microorganisms ⁇ Shimwellia microorganisms Genus microorganisms, Rhodosporidium genus microorganisms, Streptomyces genus microorganisms, Microbacterium genus microorganisms, Planomicrobium genus microorganisms, Rhodosporidium genus microorganisms, Saccharomyces genus microorganisms, Yersinia genus microorganisms.
- microorganisms belonging to the genus Serratia that have the ability to produce 3-oxoadipic acid include Serratia plymuthica, Serratia grimesii, Serratia ficola, Serratia fontilla, Serratia neratoferienta, Serratia neratoferienta, Serratia neratoferienta, Serratia neratoferienta, Serratia neratoferienta, Serratia neratoferatia.
- the mechanism by which Serratia microorganisms can produce 3-oxoadipic acid using metabolic pathways is not clear, but Serratia microorganisms may be used in wastewater treatment methods that reduce the excess sludge discharged. (See JP 2002-18469 A), which has a complicated metabolic pathway different from microorganisms generally used for substance production, and is estimated to produce 3-oxoadipic acid based on the metabolic pathway.
- microorganisms belonging to the genus Corynebacterium having the ability to produce 3-oxoadipic acid include Corynebacterium glutamicum, Corynebacterium acetoacidophilum, Corynebacterium acetoglutamicum, and Corynebacterium.
- Corynebacterium microorganisms may be used in wastewater treatment methods that reduce excess sludge discharged. (See Japanese Patent Application Laid-Open No. 2002-18469), although it is a microorganism generally used for substance production, it also has a complicated metabolic pathway different from the metabolic pathway for normal substance production. It is presumed to produce 3-oxoadipic acid based on the route.
- microorganisms belonging to the genus Psuedomonas having the ability to produce 3-oxoadipic acid include Pseudomonas putida, Pseudomonas fraggi, Pseudomonas fluorescens, Pseudomonas reptilivora and Pseudomonas.
- Psuedomonas microorganisms are aromatic hydrocarbon solvents, petroleum hydrocarbon solvents, ester solvents, alcohols.
- microorganisms belonging to the genus Bacillus having the ability to produce 3-oxoadipic acid include Bacillus magaterium and Bacillus badius. Although the mechanism by which Bacillus microorganisms can produce 3-oxoadipic acid using metabolic pathways is not clear, Bacillus microorganisms are used to deodorize malodorous substances generated during fermentation of organic waste (Japanese Patent Laid-Open No. 2001-120945), although it is a microorganism generally used for substance production, it also has a complicated metabolic pathway different from the metabolic pathway for normal substance production. Is estimated to produce 3-oxoadipic acid based on
- Hafnia spp. Microorganisms capable of producing 3-oxoadipic acid include Hafnia alvei. Although the mechanism by which Hafnia microorganisms can produce 3-oxoadipic acid using metabolic pathways is not clear, Hafnia microorganisms are used to improve the rate of terephthalic acid degradation of terephthalic acid-containing waste liquids. (Refer to Japanese Patent Laid-Open No. 10-52256), which has a complicated metabolic pathway different from microorganisms generally used for substance production, and can produce 3-oxoadipic acid based on the metabolic pathway. Presumed.
- microorganisms belonging to the genus Escherichia having the ability to produce 3-oxoadipic acid include Escherichia coli and Escherichia fergusonii.
- the mechanism by which Escherichia microorganisms can produce 3-oxoadipic acid using metabolic pathways is not clear, but Escherichia is known to have hydrocarbon resolution and heavy metal resistance (Bioresource Technology). , 2011, 102, 19, 9291-9295), although it is a microorganism generally used for substance production, it also has a complicated metabolic pathway different from the metabolic pathway in normal substance production, It is estimated that 3-oxoadipic acid is produced based on the metabolic pathway.
- Acinetobacter microorganisms having the ability to produce 3-oxoadipic acid include Acinetobacter radioresistences. Although the mechanism by which microorganisms belonging to the genus Acinetobacter can produce 3-oxoadipic acid using metabolic pathways is not clear, the genus Acinetobacter is used for environmental purification by decomposing mineral oils such as benzene, fuel oil and lubricating oil. (See JP 2013-123418 A), which has a complicated metabolic pathway different from that of microorganisms generally used for substance production. It is presumed to produce adipic acid.
- Alcaligenes microorganisms having the ability to produce 3-oxoadipic acid include Alcaligenes faecalis.
- the mechanism by which Alcaligenes microorganisms can produce 3-oxoadipic acid using metabolic pathways is not clear, but Alcaligenes is known to be used for the degradation of polycyclic aromatic compounds such as pyrene. (Refer to Japanese Patent Laid-Open No. 2003-70463), which has a complicated metabolic pathway different from microorganisms generally used for substance production, and can produce 3-oxoadipic acid based on the metabolic pathway. Presumed.
- microorganism belonging to the genus Shimwellia having the ability to produce 3-oxoadipic acid include Shimwellia brattae.
- the mechanism by which the microorganisms of the genus Shimwellia can produce 3-oxoadipic acid using metabolic pathways is not clear, the genus Shimwellia may also live in places with high radioactive radon concentrations (Radiation Protection and Environment, 2014, 37, 21, 21-24), having a complicated metabolic pathway different from microorganisms generally used for substance production, and producing 3-oxoadipic acid based on the metabolic pathway Is done.
- microorganism belonging to the genus Planomicrobium having the ability to produce 3-oxoadipic acid include Planomicrobium okeanokoites.
- the mechanism by which the microorganism of the genus Planomicrobium can produce 3-oxoadipic acid using the metabolic pathway is not clear, the genus Planomicrobium is known to decompose diesel oil (Journal of Basic Microbiology, Volume 53, Issue 9, pages 723-732), has a complicated metabolic pathway different from microorganisms commonly used for substance production, and is estimated to produce 3-oxoadipic acid based on this metabolic pathway Is done.
- Nocardioides genus microorganisms capable of producing 3-oxoadipic acid include Nocardioides albus. Although the mechanism by which Nocardioides microorganisms can produce 3-oxoadipic acid using metabolic pathways is not clear, the genus Nocardioides is sometimes used for the degradation of persistent aromatic compounds (Japanese Patent Application Laid-Open No. 2003-208867). 2003-250529)), it has a complicated metabolic pathway different from microorganisms generally used for substance production, and it is estimated that 3-oxoadipic acid is produced based on the metabolic pathway.
- microorganism belonging to the genus Yarrowia having the ability to produce 3-oxoadipic acid include Yarrowia lipolytica.
- the mechanism by which the microorganisms of the genus Yarrowia can produce 3-oxoadipic acid using the metabolic pathway is not clear, the genus Yarrowia is sometimes used for the decomposition of fats and oils and fatty acids (Japanese Patent Laid-Open No. 2015-192611). It has a complicated metabolic pathway different from microorganisms generally used for substance production, and it is presumed that 3-oxoadipic acid is produced based on the metabolic pathway.
- Capriavidus necator As a specific example of the microorganism of the genus Cupriavidus having the ability to produce 3-oxoadipic acid, there is Cupriavidus necator. Although the mechanism by which Capriavidus microorganisms can produce 3-oxoadipic acid using metabolic pathways is not clear, Capriavidus genus decomposes hydrocarbons derived from petroleum products such as benzene, toluene and xylene ( JP-A-2007-252285) and may be known to have metal resistance (Antonie van Leeuwenhoek, 2009, 96, 2, 115-139). Capriavidus microorganisms are generally used for substance production. It has a complicated metabolic pathway different from that of the microorganism to be used, and it is presumed that 3-oxoadipic acid is produced based on the metabolic pathway.
- Rhodosporidium microorganisms having the ability to produce 3-oxoadipic acid include Rhodosporium toruloides.
- the mechanism by which Rhodosporidium microorganisms can produce 3-oxoadipic acid using metabolic pathways is not clear, but Rhodosporidium spp. Are known to degrade diesel oil (Research Journal of Environmental Toxicology). 5 (6): 369-377, 2011), which has a complicated metabolic pathway different from microorganisms generally used for substance production, and is estimated to produce 3-oxoadipic acid based on this metabolic pathway Is done.
- Streptomyces microorganisms having the ability to produce 3-oxoadipic acid include Streptomyces olivaceus. Although the mechanism by which Streptomyces microorganisms can produce 3-oxoadipic acid using metabolic pathways is not clear, Streptomycins is sometimes used for the degradation of polyhydroalkanoate resins (WO05 / 045017). ), Although it is a microorganism generally used for substance production, it also has a complex metabolic pathway different from the metabolic pathway for normal substance production. Based on this metabolic pathway, 3-oxoadipic acid is added. It is estimated to generate.
- Microbacterium amphiphilum examples include Microbacterium amphiphilum. Although the mechanism by which Microbacterium genus microorganisms can produce 3-oxoadipic acid using metabolic pathways is not clear, Microbacterium genus is sometimes used in a method for treating lignin-containing waste liquid (JP 2009-72162 A). ), which has a complicated metabolic pathway different from that of microorganisms generally used for substance production, and it is presumed that 3-oxoadipic acid is produced based on the metabolic pathway.
- microorganism belonging to the genus Planomicrobium having the ability to produce 3-oxoadipic acid include Planomicrobium okeanokoites. Although the mechanism by which the microorganism of the genus Planomicrobium can produce 3-oxoadipic acid using a metabolic pathway is not clear, the genus Planomicrobium is sometimes used for biodegradation of benzene and its derivatives (Res Microbiol. 2006). Sep; 157 (7): 629-36), presumed to have a complicated metabolic pathway different from microorganisms generally used for substance production and to produce 3-oxoadipic acid based on the metabolic pathway Is done.
- Rhodosporidium microorganisms having the ability to produce 3-oxoadipic acid include Rhodosporium toruloides. Although the mechanism by which Rhodosporidium microorganisms can produce 3-oxoadipic acid using metabolic pathways is not clear, Rhodosporidium genus is sometimes used for biodegradation of diesel oil (Research Journal of Environmental Toxicology 5.). 6 (Nov / Dec 2011): 369-377), which has a complicated metabolic pathway different from microorganisms generally used for substance production, and can produce 3-oxoadipic acid based on the metabolic pathway Presumed.
- microorganisms belonging to the genus Saccharomyces having the ability to produce 3-oxoadipic acid include Saccharomyces cerevisiae. Although the mechanism by which Saccharomyces microorganisms can produce 3-oxoadipic acid using metabolic pathways is not clear, the genus Saccharomyces may decompose methyl red which is an azo dye (Chemosphere. 2007 Jun; 68 ( 2): 394-400), although it is a microorganism generally used for substance production, it also has a complicated metabolic pathway different from the metabolic pathway for normal substance production. It is presumed to produce 3-oxoadipic acid.
- Saccharomyces cerevisiae Although the mechanism by which Saccharomyces microorganisms can produce 3-oxoadipic acid using metabolic pathways is not clear, the genus Saccharomyces may decompose methyl red which is an azo dye (Chemosphere. 2007 Jun; 68 ( 2): 394-400), although it is a
- microorganisms belonging to the genus Yersinia having the ability to produce 3-oxoadipic acid include Yersinia ruckeri.
- the mechanism by which microorganisms of the genus Yersinia can produce 3-oxoadipic acid using metabolic pathways is not clear, but Yersinia genus may be involved in biodegradation of agricultural chemicals (Revista International de Continental Ambient; Vol. 26 , No. 1 (2010); 27-38), it has a complicated metabolic pathway different from microorganisms generally used for substance production, and it is estimated that 3-oxoadipic acid is generated based on this metabolic pathway Is done.
- microorganisms are all known as microorganisms existing in nature, and can be isolated from the natural environment such as soil. It can also be purchased from a microorganism dispensing organization such as ATCC.
- the microorganism may be one obtained by recombining a gene according to a known method so that the productivity of 3-oxoadipic acid is increased, or may be one obtained by mutating by an artificial mutation means. .
- Confirmation that the microorganism has the ability to produce 3-oxoadipic acid can be obtained by analyzing the supernatant of the culture solution using an appropriate analytical method such as high performance liquid chromatography (HPLC), high performance liquid chromatography mass spectrometer (LC / MS). , 3-oxoadipine contained in culture supernatant using high performance liquid chromatography tandem mass spectrometer (LC-MS / MS), gas chromatography (GC), gas chromatograph mass spectrometer (GC / MS), etc. This can be confirmed by detecting the acid.
- HPLC high performance liquid chromatography
- LC / MS high performance liquid chromatography mass spectrometer
- GC gas chromatography
- GC / MS gas chromatograph mass spectrometer
- a microorganism capable of producing 1.0 mg / L or more of 3-oxoadipic acid in a culture supernatant obtained by culturing for 20 hours is used as a microorganism capable of producing 3-oxoadipic acid. It is preferable.
- the microorganism is cultured in a medium suitable for the microorganism to be used, for example, a medium containing an aliphatic compound that can be metabolized by a normal microorganism as a carbon source, preferably a liquid medium.
- a medium suitable for the microorganism to be used for example, a medium containing an aliphatic compound that can be metabolized by a normal microorganism as a carbon source, preferably a liquid medium.
- “metabolism” in the present invention means that a certain chemical substance taken from outside the cell or produced from another chemical substance in the cell is converted into another chemical substance by an enzymatic reaction. Point to.
- a medium containing a nitrogen source, an inorganic salt, and if necessary, organic micronutrients such as amino acids and vitamins is used.
- any of a natural medium and a synthetic medium can be used as long as the nutrient source is contained.
- the said microorganism since the said microorganism is well-known and the culture method and the culture medium to be used are also well-known, it can culture using the well-known culture medium and culture
- Examples of the aliphatic compounds that can be metabolized by the microorganism as a carbon source include sugars such as glucose, sucrose, fructose, galactose, mannose, xylose, and arabinose, starch saccharified solution containing these saccharides, molasses, cellulose-containing biomass saccharified solution, Furthermore, organic acids such as acetic acid, succinic acid, lactic acid, fumaric acid, citric acid, propionic acid, malic acid, malonic acid, monohydric alcohols such as methanol, ethanol, propanol, and glycerin, ethylene glycol, propanediol, etc. Examples include polyhydric alcohols, hydrocarbons, fatty acids, oils and fats.
- any of the above compounds may be used as long as it is an aliphatic compound that can be metabolized by a microorganism, but an aliphatic compound that can be used for growth as a single carbon source by a microorganism is preferred.
- aliphatic compounds include glucose, xylose, glycerol, succinic acid, and acetic acid. More preferably, 3-oxoadipic acid can be efficiently produced by metabolizing an organic acid and a saccharide, or an organic acid and an alcohol, or two or more organic acids together. In this case, either one of the aliphatic compounds to be metabolized may be taken from outside the cell by the microorganism, or may be produced from another chemical substance in the cell.
- organic acids and saccharides in such combinations include, for example, succinic acid and glucose, and succinic acid and xylose.
- organic acids and alcohols include, for example, succinic acid and glycerol.
- the organic acid include succinic acid and acetic acid.
- the concentration of the aliphatic compound that can be metabolized is not particularly limited as long as it is a concentration that can maintain the microorganism to be cultured, and a known concentration can be adopted for each microorganism. 5 g / L to 300 g / L, especially 10 g / L to 150 g / L (total concentration when two or more aliphatic compounds are included).
- Examples of the nitrogen source used for culturing the microorganism include ammonia gas, aqueous ammonia, ammonium salts, urea, nitrates, and other auxiliary organic nitrogen sources such as oil lees, soybean hydrolysate, and casein decomposition. Products, other amino acids, vitamins, corn steep liquor, yeast or yeast extract, meat extract, peptides such as peptone, various fermented cells and hydrolysates thereof.
- the nitrogen sources can be used alone or in combination of two or more, and an inorganic nitrogen source and an organic nitrogen source can be used in combination.
- the concentration of the nitrogen source is not particularly limited as long as the microorganism to be cultured can be maintained, and a known concentration can be adopted for each microorganism. Usually, the concentration is about 0.1 g / L to 50 g / L, In particular, it is about 0.5 g / L to 10 g / L (total concentration when two or more types of nitrogen sources are included).
- the inorganic salts used for culturing the microorganism for example, phosphates, magnesium salts, calcium salts, iron salts, manganese salts and the like can be appropriately added and used.
- the concentration of these inorganic salts is not particularly limited as long as the concentration of the inorganic salts is a concentration that can maintain the microorganism to be cultured, and a known concentration can be adopted for each microorganism. For each, it is usually about 1 g / L to 50 g / L, particularly about 5 g / L to 20 g / L.
- the culture conditions for the microorganisms for producing 3-oxoadipic acid include the medium of the component composition, the culture temperature, the stirring speed, the pH, the aeration rate, the inoculation amount, the culture time, etc. It can be set by appropriately adjusting or selecting according to the external conditions.
- the culture temperature is about 10 ° C. to 50 ° C., especially about 20 ° C. to 40 ° C.
- the pH is about 3 to 9, particularly about 5 to 7
- the culture time is about 1 to 200 hours, especially 24.
- the time can be exemplified by about 150 hours, but is not limited to these.
- an antifoaming agent such as mineral oil, silicone oil and surfactant can be appropriately added to the medium.
- 3-oxoadipic acid can be produced by culturing using the microorganism, but the metabolic pathway necessary to produce 3-oxoadipic acid was activated. By culturing the microorganism in a state, 3-oxoadipic acid can be produced more efficiently.
- the method for activating the metabolic pathway is not particularly limited. For example, a method for inducing the expression of the enzyme gene (s) in the metabolic pathway for producing 3-oxoadipic acid by adding an inducer to the medium.
- a method of modifying the coding region of the enzyme gene (s) and / or a functional region around the enzyme gene (s) by gene modification technology, a method of increasing the copy number of the enzyme gene (s), an enzyme in the biosynthetic pathway of by-products examples include a method of destroying gene function, and a method of inducing expression of an enzyme gene (s) in a metabolic pathway for producing 3-oxoadipic acid by an inducer is preferable.
- the inducer used in the present invention is not particularly limited as long as it is a substance that activates a metabolic pathway necessary for the production of 3-oxoadipic acid.
- 3-oxoadipyl-CoA is used as an intermediate to increase the number of carbon atoms.
- An aromatic compound or an aliphatic compound having 6 or more carbon atoms that is metabolized to a compound having a small amount of carbon can be used.
- a dicarboxylic acid having 6 or more carbon atoms can be preferably used as the aliphatic compound having 6 or more carbon atoms.
- Examples of such compounds can be known using databases such as KEGG (Kyoto Encyclopedia of Genes and Genomes), and specifically, benzoic acid, cis, cis-muconic acid, terephthalic acid, protocatechuic acid , Catechol, vanillin, coumaric acid, ferulic acid, adipic acid, phenylalanine, phenethylamine, and the like.
- Preferred examples include benzoic acid, catechol, protocatechuic acid, and adipic acid.
- the above inducers may be used alone or in combination of two or more according to the microorganism used for the production of 3-oxoadipic acid.
- the concentration of the inducer is not particularly limited and can be appropriately set, but is usually about 1 mg / L to 10 g / L, particularly about 3 mg / L to 1 g / L (two or more inducers are used). In that case the total concentration).
- Isolation of 3-oxoadipic acid produced in the culture of the microorganism is a general method of stopping the culture when the accumulated amount has increased moderately and collecting the fermentation product from the culture. It can be done according to this. Specifically, for example, after microbial cells are separated by centrifugation, filtration, etc., the 3-oxoadipic acid is cultured by column chromatography, ion exchange chromatography, activated carbon treatment, crystallization, membrane separation, distillation, etc. Can be isolated from More specifically, as a preferred recovery method, the culture is concentrated by using a reverse osmosis membrane or an evaporator to remove water to increase the concentration of 3-oxoadipic acid, followed by cooling crystallization or adiabatic crystallization.
- Examples include a method of adding alcohol to a product to obtain 3-oxoadipic acid ester, recovering 3-oxoadipic acid ester by distillation, and then obtaining 3-oxoadipic acid by hydrolysis. It is not limited.
- Examples of the salt of 3-oxoadipic acid include Na salt, K salt, Ca salt, Mg salt or ammonium salt.
- Example 1 3-oxoadipic acid production test using an aliphatic compound [microbe culture] The production ability of 3-oxoadipic acid of the microorganisms shown in Table 1 below (all microorganisms were purchased from a microorganism distribution organization and the purchaser is listed in the stock name) was examined.
- 0.5 mL of the suspension was added to 5 mL of a medium having the following composition using an aliphatic compound as a carbon source, and cultured with shaking at 30 ° C. for 20 hours (main culture).
- the supernatant obtained by centrifuging cells from the main culture was analyzed by LC-MS / MS.
- the concentration of 3-oxoadipic acid accumulated in the culture supernatant was as shown in Table 1, and it was confirmed that all the microorganisms had the ability to produce 3-oxoadipic acid.
- Example 2 3-Oxoadipic acid production test using a single aliphatic compound plymuthica NBRC102599, C.I. glutamicum ATCC 13826 and P. Fragi NBRC3458 was cultured under the same conditions as in Example 1 except that 10 g / L of succinic acid, glucose, or glycerol was included as a single carbon source in the main culture. Quantitative analysis of oxoadipic acid was performed. The results for the three microorganism strains are shown in Tables 2 to 4, respectively.
- Growth test medium composition (C. glutamicum): Carbon source 10g / L Ammonium sulfate 1g / L Potassium phosphate 50 mM Magnesium sulfate 0.025g / L Iron sulfate 0.0625mg / L Manganese sulfate 2.7mg / L Calcium chloride 0.33mg / L Sodium chloride 1.25g / L Biotin 0.03mg / L Thiamine hydrochloride 1mg / L Protocatechuic acid 1mg / L pH 6.5.
- Example 3 3-oxoadipic acid production test using two kinds of aliphatic compounds plymuthica NBRC102599, C.I. glutamicum ATCC 13826 and P. Fragi NBRC3458 was cultured under the same conditions as in Example 1 except that 10 g / L of each of the two aliphatic compounds shown in Tables 8 to 10 was used as the carbon source in the main culture. Quantitative analysis of adipic acid was performed. At the same time, succinic acid alone was used as a control as a carbon source, and the difference from the control 3-oxoadipic acid accumulation concentration was determined. The results for the three microorganism strains are shown in Tables 8 to 10, respectively.
- Example 4 3-Oxoadipic acid production test using a single inducer plymuthica NBRC102599, C.I. glutamicum ATCC 13826 and P.
- Fragi NBRC3458 is pre-cultured using a medium containing 2.5 mM of the compound shown in Tables 11 to 13 as an inducer, or a medium containing no inducer, and 10 g each of succinic acid and glucose as carbon sources in the main culture.
- the cells were cultured under the same conditions as in Example 1 except that a medium containing / L was used, and quantitative analysis of 3-oxoadipic acid in the culture supernatant was performed.
- the results for the three microorganism strains are shown in Tables 11 to 13, respectively.
- Example 5 Production Example of 3-oxoadipic acid Serratia pymuthica NBRC102599, which was confirmed to be a microorganism capable of producing 3-oxoadipic acid in Example 1, was inoculated into 5 mL of LB medium by one platinum ear, The suspension was cultured at 30 ° C. until suspended (pre-culture).
- 2 mL of the previous culture solution was tryptone 10 g / L, yeast extract 5 g / L, sodium chloride 5 g / L, benzoic acid 2.5 mM, catechol 2.5 mM, cis, cis-muconic acid 2.5 mM, terephthalic acid 2.5 mM, The mixture was added to 100 mL of a medium consisting of 2.5 mM protocatechuic acid, 2.5 mM adipic acid, 2.5 mM phenylalanine, 2.5 mM phenethylamine, pH 7, and cultured with shaking at 30 ° C. until fully suspended (preculture).
- Example 2 After washing the precultured solution with 200 mL of 0.9% sodium chloride three times in the same manner as in Example 1, the cells were suspended in 10 mL of 0.9% sodium chloride. 10 mL of the suspension was added to 100 mL of the main culture medium similar to Example 1, and cultured with shaking at 30 ° C. for 20 hours (main culture). The supernatant obtained by centrifuging cells from the main culture was analyzed by LC-MS / MS in the same manner as in Example 1. As a result, the concentration of 3-oxoadipic acid accumulated in the culture supernatant was 260 mg / L. there were.
- the supernatant of the main culture was concentrated under reduced pressure to obtain 12 mL of a concentrated solution having a 3-oxoadipic acid concentration of 2200 mg / L.
- This concentrated solution was injected into an HPLC connected with a preparative device, and a fraction having an elution time corresponding to the preparation of 3-oxoadipic acid was collected. This operation was repeated 10 times to obtain a 3-oxoadipic acid aqueous solution from which impurities in the culture medium were removed.
- the preparative HPLC used for collecting 3-oxoadipic acid was performed under the following conditions.
- Comparative Example 1 Microorganisms not having the ability to produce 3-oxoadipic acid
- the microorganisms shown in Table 14 to produce 3-oxoadipic acid were cultured under the same conditions as in Example 1, As a result of quantitative analysis of oxoadipic acid, 3-oxoadipic acid was not detected in the culture supernatant.
- Comparative Example 2 Culture without addition of carbon source
- the microorganisms shown in Table 1 were subjected to the same conditions as in Example 1 except that a medium having a composition not containing an aliphatic compound (succinic acid, glucose, glycerol) as a carbon source was used.
- a medium having a composition not containing an aliphatic compound succinic acid, glucose, glycerol
- 3-oxoadipic acid was not detected in the culture supernatant. From this result, it was confirmed that 3-oxoadipic acid quantified in Example 1 was produced as a result of metabolism of an aliphatic compound by a microorganism.
- Example 6 3-oxoadipic acid production test using various microorganisms
- the microorganisms shown in Table 15 were used as inducers.
- Pre-culture and fungus under the same conditions as in Example 1 except that ferulic acid, p-coumaric acid, benzoic acid, cis, cis-muconic acid, protocatechuic acid and catechol were added to the culture medium to 2.5 mM each.
- Body washing was performed. 0.5 mL of the suspension after washing was added to 5 mL of a medium having the composition shown below, and cultured with shaking at 30 ° C. for 48 hours.
- Table 15 shows the results of quantitative analysis of 3-oxoadipic acid accumulated in the culture supernatant. From these results, it was confirmed that all the microorganisms have the ability to produce 3-oxoadipic acid.
- Example 7 3-Oxoadipic acid production test without addition of inducer Pre-culture under the same conditions as in Example 6 except that the inducer used in Example 6 was not added to the microorganisms shown in Table 16. The cells were washed. 0.5 mL of the suspension after washing was added to 5 mL of a medium having the composition shown below, and cultured with shaking at 30 ° C. for 48 hours.
- Table 16 shows the results of quantitative analysis of 3-oxoadipic acid in the culture supernatant.
- Example 8 3-oxoadipic acid production test using p-coumaric acid or ferulic acid as inducer From among the substances added to the preculture medium as inducer in Example 6 for the microorganisms shown in Table 17 Pre-culture and cell washing were performed under the same conditions as in Example 6 except that p-coumaric acid or ferulic acid was added to a concentration of 0.5 mM. 0.5 mL of the suspension after washing was added to 5 mL of the medium having the composition shown in Example 7, and cultured with shaking at 30 ° C. for 48 hours. Table 17 shows the results of quantitative analysis of 3-oxoadipic acid in the culture supernatant.
- Example 9 3-oxoadipic acid production test using various concentrations of ferulic acid as inducer From among the substances added to the preculture medium as inducer in Example 6 for the genus microorganisms shown in Table 18 Ferulic acid was added to the preculture medium of Example 7 so as to have a concentration shown in Table 18, and preculture was performed. Main culture was performed under the same conditions as in Example 7, and quantitative analysis of 3-oxoadipic acid in the culture supernatant was performed. The results are shown in Table 18, respectively. From these results, it was found that even when ferulic acid alone was added to the preculture medium as an inducer, the production amount of 3-oxoadipic acid was improved.
- Example 10 3-oxoadipic acid production test using various concentrations of p-coumaric acid as an inducer Among the substances added to the preculture medium as an inducer in Example 6 for the microorganisms shown in Table 19 Thus, p-coumaric acid was added to the preculture medium of Example 7 so as to have the concentration shown in Table 19, and preculture was performed. Main culture was performed under the same conditions as in Example 7, and quantitative analysis of 3-oxoadipic acid in the culture supernatant was performed. The results are shown in Table 19, respectively. From these results, it was found that when only p-coumaric acid was added to the preculture medium as an inducer, the production amount of 3-oxoadipic acid was improved.
- Cellulase concentration in an aqueous solution was based on the value of protein concentration (mg / mL) in the enzyme solution measured by the Bradford method. Protein concentration was measured using a Bradford assay kit (Quick Start Bradford Protein Assay, Bio-Rad).
- the obtained solid-liquid separated solid is suspended again at a solid content concentration of 5%, and the filamentous fungus-derived cellulase prepared in Reference Example 3 is hydrolyzed with a protein amount of 8 mg / g-bagasse by the measurement shown in Reference Example 4 to be saccharified.
- a liquid was obtained.
- the hydrolysis conditions were 40 ° C., pH 7.0, and reaction time 24 hours.
- the obtained saccharified solution is solid-removed with a screw decanter, and the recovered saccharified solution is filtered through a microfiltration membrane having a pore size of 0.22 ⁇ m, and the resulting permeate is filtered through an ultrafiltration membrane. Went.
- TMUS10k Toray Membrane USA, material: polyvinylidene fluoride, molecular weight cut off: 10,000
- SEPA-II manufactured by GE Osmonics
- the amount of liquid recovered from the non-permeate side is 0.6 L under the conditions of a membrane surface linear velocity of 20 cm / second and a filtration pressure of 3 MPa. Filtration treatment was performed until a saccharified solution was obtained on the permeate side.
- the obtained saccharified solution was filtered through a separation membrane (manufactured by Synder, NFW (material: piperazine polyamide, molecular weight cut off: 300 to 500)).
- the filtration was performed under the conditions of a membrane surface linear velocity of 20 cm / sec and a filtration pressure of 3 MPa until the concentration rate on the non-permeate side was 12 times to obtain a saccharified solution on the permeate side.
- the obtained saccharified solution was concentrated with an evaporator to prepare a saccharified solution of glucose 100 g / L, xylose 22.3 g / L, coumaric acid 0.5 g / L, and ferulic acid 0.06 g / L.
- the saccharified solution was adjusted with 6N sodium hydroxide so that the final pH was 7.
- Example 11 3-oxoadipic acid production test using cellulose-containing biomass-derived saccharified solution 3-oxoadipic acid production test using the cellulose-containing biomass-derived saccharified solution prepared in Reference Example 5 as a carbon source for the microorganisms shown in Table 20 Adipic acid production test was conducted.
- a cellulose-containing biomass-derived saccharified solution shaking culture was performed at 5 ° C. in 5 mL of a preculture medium adjusted to have the following composition until the respective microorganisms were sufficiently suspended (preculture). Subsequently, the cells were washed under the same conditions as in Example 6. 0.5 mL of the suspension after washing was added to 5 mL of a main culture medium adjusted to have the composition shown below using a cellulose-containing biomass-derived saccharified solution, and cultured with shaking at 30 ° C. for 48 hours. For comparison, culturing was carried out under the same conditions as described above except that a carbon source containing no p-coumaric acid and ferulic acid was used for the preculture and the main culture.
- Table 20 shows the results of quantitative analysis of 3-oxoadipic acid in the culture supernatant. From these results, even when culturing using a cellulose-containing biomass-derived saccharified solution containing p-coumaric acid and ferulic acid, compared with the case of using a carbon source not containing p-coumaric acid and ferulic acid, 3 It was found that the production amount of oxoadipic acid was improved.
- Pre-culture medium composition glucose 5g / L Xylose 1.1g / L p-coumaric acid 25mg / L Ferulic acid 3mg / L Ammonium sulfate 1g / L Potassium phosphate 50 mM Magnesium sulfate 0.025g / L Iron sulfate 0.0625mg / L Manganese sulfate 2.7mg / L Calcium chloride 0.33mg / L Sodium chloride 1.25g / L Bacto tryptone 2.5g / L Yeast extract 1.25g / L pH 6.5.
- Example 12 3-oxoadipic acid production test using two types of carbon sources
- pre-culture was performed using the same medium as in Example 6, and then the carbon source And cultured in a medium containing 10 g / L of each of the compounds shown in Table 21 and Table 22 under the same conditions as in Example 6, and quantitative analysis of 3-oxoadipic acid in the culture supernatant was performed.
- the results are shown in Table 21 and Table 22, respectively. From these results, it was found that 3-oxoadipic acid can be efficiently produced even when cultured using two types of carbon sources.
- Example 13 3-oxoadipic acid production test using two types of carbon sources at various concentrations
- Pre-culture was performed using the same medium as in Example 6 for the microorganisms shown in Table 23 and Table 24. Thereafter, the cells were cultured for 48 to 120 hours under the same conditions as in Example 6 in media containing the compounds at the concentrations shown in Table 23 and Table 24 as carbon sources, and the amount of 3-oxoadipic acid in the culture supernatant was determined. Analyzed. The results are shown in Table 23 and Table 24, respectively. From these results, it was found that 3-oxoadipic acid can be produced even if the addition ratio of the carbon source is changed.
- Example 14 3-Oxoadipic acid production test using a single carbon source
- preculture without adding an inducer was performed using the same medium as in Example 7.
- the cells are cultured in a medium containing 10 g / L of succinic acid, glucose, or glycerol as a carbon source under the same conditions as in Example 7.
- Quantitative analysis of 3-oxoadipic acid in the culture supernatant Did. The results are shown in Table 24, respectively. Further, the same experiment was performed by changing to the conditions of Example 6 in which an inducer was added only to the preculture medium.
- the production amount of 3-oxoadipic acid is shown in Table 25.
- 3-oxoadipic acid can be produced using microorganisms.
- the obtained 3-oxoadipic acid can be used as various polymer raw materials.
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Abstract
Description
・Serratia属微生物
・Corynebacterium属微生物
・Pseudomonas属微生物
・Bacillus属微生物
・Hafnia属微生物
・Escherichia属微生物
・Acinetobacter属微生物
・Alcaligenes属微生物
・Shimwellia属微生物
・Planomicrobium属微生物
・Nocardioides属微生物
・Yarrowia属微生物
・Cupriavidus属微生物
・Rhodosporidium属微生物
・Streptomyces属微生物
・Microbacterium属微生物
・Planomicrobium属微生物
・Rhodosporidium属微生物
・Saccharomyces属微生物
・Yersinia属微生物。
微生物が生産した3-オキソアジピン酸の定量分析に使用する当該物質の標品は化学合成により準備した。
1H-NMR(400MHz、D2O):δ2.62(t、2H)、δ2.88(t、2H)、δ3.73(s、1H)。
[微生物培養]
以下の表1に示した微生物(いずれの微生物も微生物分与機関より購入。購入先は株名に記載。)の3-オキソアジピン酸の生産能を調べた。トリプトン10g/L、酵母エキス5g/L、塩化ナトリウム5g/Lに誘導物質として安息香酸、cis,cis-ムコン酸、テレフタル酸、プロトカテク酸、カテコール、アジピン酸、フェニルアラニンおよびフェネチルアミンをそれぞれ2.5mMとなるように添加しpH7に調製した培地5mLに、それぞれの微生物を一白金耳植菌し、十分懸濁するまで30℃で振とう培養した(前培養)。その培養液に10mLの0.9%塩化ナトリウムを加え、菌体を遠心分離したのち上清を完全に取り除くことで菌体を洗浄する操作を3回行ったのち、菌体を1mLの0.9%塩化ナトリウムに懸濁した。懸濁液0.5mLを、脂肪族化合物を炭素源とする以下に示した組成の培地5mLに添加し、30℃で20時間振とう培養した(本培養)。本培養液より菌体を遠心分離した上清を、LC-MS/MSにて分析した。
コハク酸10g/L
グルコース10g/L
グリセロール10g/L
硫酸アンモニウム1g/L
リン酸カリウム50mM
硫酸マグネシウム0.025g/L
硫酸鉄0.0625mg/L
硫酸マンガン2.7mg/L
塩化カルシウム0.33mg/L
塩化ナトリウム1.25g/L
Bactoトリプトン2.5g/L
酵母エキス1.25g/L
pH6.5。
LC-MS/MSによる3-オキソアジピン酸の定量分析は以下の条件で行った。
・HPLC:1290Infinity(Agilent Technologies社製)
カラム:Synergi hydro-RP(Phenomenex社製)、長さ100mm、内径3mm、粒径2.5μm
移動相:0.1%ギ酸水溶液/メタノール=70/30
流速:0.3mL/分
カラム温度:40℃
LC検出器:DAD(210nm)
・MS/MS:Triple-Quad LC/MS(Agilent Technologies社製)
イオン化法:ESI ネガティブモード。
S.plymuthica NBRC102599、C.glutamicum ATCC13826およびP.fragi NBRC3458それぞれを、本培養における単一炭素源としてコハク酸、グルコース、グリセロールのいずれか1つを10g/L含む他は実施例1と同様の条件にて培養し、培養上清中の3-オキソアジピン酸の定量分析をした。微生物3株についての結果をそれぞれ表2から4に示す。
S.plymuthica NBRC102599、C.glutamicum ATCC13826およびP.fragi NBRC3458それぞれを、培養における単一炭素源として表5から7に示す脂肪族化合物のいずれか1つを10g/L含む生育試験用培地に一白金耳植菌し、30℃で振とう培養した。培養開始から2日後に培養液の濁度(McFarland units)をデンシトメーターDEN-1B(ワケンビーテック株式会社製)を用いて測定した。同時にコントロールとして炭素源を添加しない培養を行い、コントロールの濁度との差分を求めた。微生物3株についての結果をそれぞれ表5から7に示す。
炭素源10g/L
硫酸アンモニウム1g/L
リン酸カリウム50mM
硫酸マグネシウム0.025g/L
硫酸鉄0.0625mg/L
硫酸マンガン2.7mg/L
塩化カルシウム0.33mg/L
塩化ナトリウム1.25g/L
pH6.5。
炭素源10g/L
硫酸アンモニウム1g/L
リン酸カリウム50mM
硫酸マグネシウム0.025g/L
硫酸鉄0.0625mg/L
硫酸マンガン2.7mg/L
塩化カルシウム0.33mg/L
塩化ナトリウム1.25g/L
ビオチン0.03mg/L
チアミン塩酸塩1mg/L
プロトカテク酸1mg/L
pH6.5。
S.plymuthica NBRC102599、C.glutamicum ATCC13826およびP.fragi NBRC3458それぞれを、本培養における炭素源として表8から10に示す脂肪族化合物2種をそれぞれ10g/L含む他は実施例1と同様の条件にて培養し、培養上清中の3-オキソアジピン酸の定量分析をした。同時にコントロールとしてコハク酸のみを炭素源とした培養を行い、コントロールの3-オキソアジピン酸蓄積濃度との差分を求めた。微生物3株についての結果をそれぞれ表8から10に示す。
S.plymuthica NBRC102599、C.glutamicum ATCC13826およびP.fragi NBRC3458それぞれを、表11から13に示す化合物を誘導物質として2.5mM含む培地、もしくは誘導物質を含まない培地を用いて前培養を行い、本培養において炭素源としてコハク酸およびグルコースをそれぞれ10g/L含む培地を用いた他は実施例1と同様の条件にて培養し、培養上清中の3-オキソアジピン酸の定量分析をした。微生物3株についての結果をそれぞれ表11から13に示す。
実施例1で3-オキソアジピン酸の生産能を有する微生物であることが確認できたSerratia plymuthica NBRC102599を、LB培地5mLに一白金耳植菌し、十分懸濁するまで30℃で振とう培養した(前々培養)。前々培養液2mLをトリプトン10g/L、酵母エキス5g/L、塩化ナトリウム5g/L、安息香酸2.5mM、カテコール2.5mM、cis,cis-ムコン酸2.5mM、テレフタル酸2.5mM、プロトカテク酸2.5mM、アジピン酸2.5mM、フェニルアラニン2.5mM、フェネチルアミン2.5mM、pH7からなる培地100mLに添加し、十分懸濁するまで30℃で振とう培養した(前培養)。前培養液を200mLの0.9%塩化ナトリウムで実施例1と同様に3回洗浄したのち、菌体を10mLの0.9%塩化ナトリウムに懸濁した。懸濁液10mLを実施例1と同様の本培養の培地100mLに添加し、30℃で20時間振とう培養した(本培養)。本培養液より菌体を遠心分離した上清を、実施例1と同様にLC-MS/MSにて分析した結果、培養上清中に蓄積した3-オキソアジピン酸の濃度は260mg/Lであった。
カラム:Synergi hydro-RP(Phenomenex社製)、長さ250mm、内径10mm、粒径4μm
移動相:5mM ギ酸水溶液/アセトニトリル=98/2
流速:4mL/分
注入量:1mL
カラム温度:45℃
検出器:UV-VIS(210nm)
分取装置:FC204(Gilson社製)。
表14に示した微生物の3-オキソアジピン酸の生産能を確認するべく、実施例1と同様の条件で微生物培養し、3-オキソアジピン酸の定量分析をした結果、培養上清中に3-オキソアジピン酸は検出されなかった。
表1に示した微生物を、脂肪族化合物(コハク酸、グルコース、グリセロール)を炭素源として含まない組成の培地を用いた他は実施例1と同様の条件で培養し、3-オキソアジピン酸の定量分析をした結果、培養上清中に3-オキソアジピン酸は検出されなかった。本結果より、実施例1で定量できた3-オキソアジピン酸は脂肪族化合物が微生物により代謝された結果生成したものであることを確認できた。
表15に示した微生物(いずれも微生物分与機関より購入。購入先は株名に記載。)を対象に、誘導物質として、前培養培地にフェルラ酸、p-クマル酸、安息香酸、cis,cis-ムコン酸、プロトカテク酸およびカテコールをそれぞれ2.5mMとなるように添加した以外は実施例1と同様の条件で前培養および菌体洗浄を行った。洗浄後の懸濁液0.5mLを以下に示した組成の培地5mLに添加し、30℃で48時間振とう培養した。
グルコース10g/L
グリセロール10g/L
硫酸アンモニウム1g/L
リン酸カリウム50mM
硫酸マグネシウム0.025g/L
硫酸鉄0.0625mg/L
硫酸マンガン2.7mg/L
塩化カルシウム0.33mg/L
塩化ナトリウム1.25g/L
Bactoトリプトン2.5g/L
酵母エキス1.25g/L
pH6.5。
表16に示した微生物を対象に、実施例6で用いた誘導物質を添加しなかった以外は実施例6と同様の条件で前培養および菌体洗浄を行った。洗浄後の懸濁液0.5mLを以下に示した組成の培地5mLに添加し、30℃で48時間振とう培養した。
グルコース10g/L
硫酸アンモニウム1g/L
リン酸カリウム50mM
硫酸マグネシウム0.025g/L
硫酸鉄0.0625mg/L
硫酸マンガン2.7mg/L
塩化カルシウム0.33mg/L
塩化ナトリウム1.25g/L
Bactoトリプトン2.5g/L
酵母エキス1.25g/L
pH6.5。
表17に示した微生物を対象に、実施例6で誘導物質として前培養培地に添加した物質の中から、p-クマル酸又はフェルラ酸をそれぞれ0.5mMとなるように添加した以外は実施例6と同様の条件で前培養および菌体洗浄を行った。洗浄後の懸濁液0.5mLを実施例7に示した組成の培地5mLに添加し、30℃で48時間振とう培養した。培養上清中の3-オキソアジピン酸の定量分析をした結果をそれぞれ表17に示す。これらの結果から、p-クマル酸又はフェルラ酸のみを誘導物質として前培養培地に添加した場合でも、添加しなかった場合と比べて、3-オキソアジピン酸の生産量が向上することがわかった。
表18に示した属微生物を対象に、実施例6で誘導物質として前培養培地に添加した物質の中から、フェルラ酸を表18に示した濃度になるよう実施例7の前培養培地に添加し、前培養を行った。実施例7と同様の条件で本培養を行い、培養上清中の3-オキソアジピン酸の定量分析をした。結果をそれぞれ表18に示す。これらの結果から、フェルラ酸のみを誘導物質として前培養培地に添加した場合でも、3-オキソアジピン酸の生産量が向上することがわかった。
表19に示した微生物を対象に、実施例6で誘導物質として前培養培地に添加した物質の中から、p-クマル酸を表19に示した濃度になるよう実施例7の前培養培地に添加し、前培養を行った。実施例7と同様の条件で本培養を行い、培養上清中の3-オキソアジピン酸の定量分析をした。結果をそれぞれ表19に示す。これらの結果から、p-クマル酸のみを誘導物質として前培養培地に添加した場合も、3-オキソアジピン酸の生産量が向上することがわかった。
糸状菌由来セルラーゼ(培養液)は、次の方法で調製した。
コーンスティープリカー(CSL)5%(w/vol)、グルコース2%(w/vol)、酒石酸アンモニウム0.37%(w/vol)、硫酸アンモニウム0.14(w/vol)、リン酸二水素カリウム0.2%(w/vol)、塩化カルシウム二水和物0.03%(w/vol)、硫酸マグネシウム七水和物0.03%(w/vol)、塩化亜鉛0.02%(w/vol)、塩化鉄(III)六水和物0.01%(w/vol)、硫酸銅(II)五水和物0.004%(w/vol)、塩化マンガン四水和物0.0008%(w/vol)、ホウ酸0.0006%(w/vol)、七モリブデン酸六アンモニウム四水和物0.0026%(w/vol)となるように蒸留水に添加し、100mLを500mLバッフル付き三角フラスコに張り込み、121℃の温度で15分間オートクレーブ滅菌した。放冷後、これとは別に、それぞれ121℃の温度で15分間オートクレーブ滅菌したPE-MとTween80を、それぞれ0.01%(w/vol)添加した。この前培養培地に、トリコデルマ・リーセイATCC66589を1×105個/mLになるように植菌し、28℃の温度で72時間、180rpmで振とう培養し、前培養とした(振とう装置:TAITEC社製 BIO-SHAKER BR-40LF)。
コーンスティープリカー(CSL)5%(w/vol)、グルコース2%(w/vol)、セルロース(旭化成ケミカルズ社製、商品名:アビセル)10%(w/vol)、酒石酸アンモニウム0.37%(w/vol)、硫酸アンモニウム0.14%(w/vol)、リン酸二水素カリウム0.2%(w/vol)、塩化カルシウム二水和物0.03%(w/vol)、硫酸マグネシウム七水和物0.03%(w/vol)、塩化亜鉛0.02%(w/vol)、塩化鉄(III)六水和物0.01%(w/vol)、硫酸銅(II)五水和物0.004%(w/vol)、塩化マンガン四水和物0.0008%(w/vol)、ホウ酸0.0006%(w/vol)、七モリブデン酸六アンモニウム四水和物0.0026%(w/vol)となるように蒸留水に添加し、2.5Lを5L容撹拌ジャー(ABLE社製、DPC-2A)容器に張り込み、121℃の温度で15分間オートクレーブ滅菌した。放冷後、これとは別に、それぞれ121℃の温度で15分間オートクレーブ滅菌したPE-MとTween80を、それぞれ0.1%添加し、あらかじめ前記の方法で液体培地で前培養したトリコデルマ・リーセイATCC66589を250mL接種した。その後、28℃の温度で87時間、300rpm、通気量1vvmの条件で振とう培養を行い、遠心分離後、上清を膜ろ過(ミリポア社製の“ステリカップ-GV”、材質:PVDF)した。この前述の条件で調整した培養液を糸状菌由来セルラーゼとして、以下の参考例に使用した。
水溶液中のセルラーゼ濃度はブラッドフォード法によって測定した酵素液中のタンパク質濃度(mg/mL)の値を基準とした。タンパク質の濃度は、ブラッドフォード法による測定キット(Quick Start Bradford Protein Assay、Bio-Rad社製)を使用して測定した。
バガス乾燥重量1kgに対し、バイオマス仕込み量5%で30gの苛性ソーダを混合し、90℃、3時間反応させアルカリ処理バガスを作製した。アルカリ処理バガスをスクリュープレスで固液分離し、含水率60%の固液分離固体を得た。
表20に示した微生物を対象に、参考例5で作製したセルロース含有バイオマス由来糖化液を炭素源として用いた3-オキソアジピン酸生産試験を行った。
グルコース5g/L
キシロース1.1g/L
p-クマル酸25mg/L
フェルラ酸3mg/L
硫酸アンモニウム1g/L
リン酸カリウム50mM
硫酸マグネシウム0.025g/L
硫酸鉄0.0625mg/L
硫酸マンガン2.7mg/L
塩化カルシウム0.33mg/L
塩化ナトリウム1.25g/L
Bactoトリプトン2.5g/L
酵母エキス1.25g/L
pH6.5。
グルコース50g/L
キシロース11g/L
p-クマル酸250mg/L
フェルラ酸30mg/L
コハク酸10g/L
硫酸アンモニウム1g/L
リン酸カリウム50mM
硫酸マグネシウム0.025g/L
硫酸鉄0.0625mg/L
硫酸マンガン2.7mg/L
塩化カルシウム0.33mg/L
塩化ナトリウム1.25g/L
Bactoトリプトン2.5g/L
酵母エキス1.25g/L
pH6.5。
表21および表22に示した微生物を対象に、実施例6と同様の培地を用いて前培養を行ったのち、炭素源として表21および表22に示した化合物をそれぞれ10g/L含む培地にて実施例6と同様の条件にて培養し、培養上清中の3-オキソアジピン酸の定量分析をした。結果をそれぞれ表21および表22に示す。これらの結果から、2種類の炭素原を用いて培養しても、3-オキソアジピン酸を効率よく生産できることがわかった。
表23および表24に示した微生物を対象に、実施例6と同様の培地を用いて前培養を行ったのち、炭素源として表23および表24に示した濃度の化合物をそれぞれ含む培地にて実施例6と同様の条件にて48~120時間培養し、培養上清中の3-オキソアジピン酸の定量分析をした。結果をそれぞれ表23および表24に示す。これらの結果から、炭素源の添加割合を変更しても、3-オキソアジピン酸を生産できることがわかった。
表24および表25に示した微生物を対象に、実施例7と同様の培地を用いて誘導物質を添加しない前培養を行ったのち、炭素源としてコハク酸、グルコース、グリセロールのいずれか1種類を10g/L含む培地にて実施例7と同様の条件にて培養し、培養上清中の3-オキソアジピン酸の定量分析をした。結果をそれぞれ表24に示す。さらに、同様の実験について、前培養培地のみ誘導物質を添加した実施例6の条件に変更して行った。3-オキソアジピン酸の生産量について表25に示す。これらの結果から、単一の炭素源を用いた場合でも、3-オキソアジピン酸を生産できること、また、単一の炭素源を用いた場合も、誘導物質を前培養培地に添加することで、3-オキソアジピン酸の生産量が向上することがわかった。
Claims (28)
- Serratia属微生物、Corynebacterium属微生物、Hafnia属微生物、Bacillus属微生物、Escherichia属微生物、Pseudomonas属微生物、Acinetobacter属微生物、Alcaligenes属微生物、Shimwellia属微生物、Planomicrobium属微生物、Nocardioides属微生物、Yarrowia属微生物、Cupriavidus属微生物、Rhodosporidium属微生物、Streptomyces属微生物、Microbacterium属微生物、Planomicrobium属微生物、Rhodosporidium属微生物、Saccharomyces属微生物およびYersinia属微生物からなる群から選択される、3-オキソアジピン酸の生産能を有する少なくとも1種の微生物を培養する工程を含む、3-オキソアジピン酸の製造方法。
- Serratia属微生物、Corynebacterium属微生物、Hafnia属微生物、Bacillus属微生物、Escherichia属微生物、Pseudomonas属微生物、Acinetobacter属微生物、Alcaligenes属微生物、Shimwellia属微生物、Planomicrobium属微生物、Nocardioides属微生物、Yarrowia属微生物、Cupriavidus属微生物、Rhodosporidium属微生物、Streptomyces属微生物、Planomicrobium属微生物、及びRhodosporidium属微生物からなる群から選択される、3-オキソアジピン酸の生産能を有する少なくとも1種の微生物を培養する工程を含む、請求項1に記載の方法。
- 前記Serratia属微生物が、Serratia plymuthica、Serratia grimesii、Serratia ficaria、Serratia fonticola、Serratia odorifera、Serratia entomophilaまたはSerratia nematodiphilaである、請求項1または2に記載の方法。
- 前記Serratia属微生物が、Serratia plymuthica、Serratia grimesiiまたはSerratia ficaria、である、請求項3に記載の方法。
- 前記Corynebacterium属微生物が、Corynebacterium glutamicum、Corynebacterium acetoacidophilum、Corynebacterium acetoglutamicumまたはCorynebacterium ammoniagenesである、請求項1または2に記載の方法。
- 前記Hafnia属微生物がHafnia alveiである、請求項1または2に記載の方法。
- 前記Bacillus属微生物が、Bacillus magaterium、Bacillus badiusまたはBacillus megateriumである、請求項1または2に記載の方法。
- 前記Bacillus属微生物が、Bacillus magateriumまたはBacillus badiusである、請求項7に記載の方法。
- 前記Escherichia属微生物が、Escherichia coliまたはEscherichia fergusoniiである、請求項1または2に記載の方法。
- 前記Pseudomonas属微生物が、Pseudomonas putida、Pseudomonas fragi、Pseudomonas fluorescens、Pseudomonas reptilivora、またはPseudomonas azotoformansである、請求項1または2に記載の方法。
- 前記Acinetobacter属微生物がAcinetobacter radioresistensである、請求項1または2に記載の方法。
- 前記Alcaligenes属微生物がAlcaligenes faecalisである、請求項1または2に記載の方法。
- 前記Shimwellia属微生物がShimwellia blattaeである、請求項1または2に記載の方法。
- 前記Planomicrobium属微生物がPlanomicrobium okeanokoitesである、請求項1または2に記載の方法。
- 前記Nocardioides属微生物がNocardioides albusである、請求項1または2に記載の方法。
- 前記Yarrowia属微生物がYarrowia lipolyticaである、請求項1または2に記載の方法。
- 前記Cupriavidus属微生物がCupriavidus necatorである、請求項1または2に記載の方法。
- 前記Rhodosporidium属微生物がRhodosporidium toruloidesである、請求項1または2に記載の方法。
- 前記Streptomyces属微生物がStreptomyces olivaceusである、請求項1または2に記載の方法。
- 前記Microbacterium属微生物がMicrobacterium ammoniaphilumである、請求項1に記載の方法。
- 前記Planomicrobium属微生物がPlanomicrobium okeanokoitesである、請求項1または2に記載の方法。
- 前記Rhodosporidium属微生物がRhodosporidium toruloidesである、請求項1または2に記載の方法。
- 前記Saccharomyces属微生物がSaccharomyces cerevisiaeである、請求項1に記載の方法。
- 前記Yersinia属微生物がYersinia ruckeriである、請求項1に記載の方法。
- 前記微生物を培養する培地が脂肪族化合物を含む、請求項1~24のいずれか1項に記載の方法。
- 前記微生物を培養する培地が、該微生物が単一炭素源として生育に利用可能な脂肪族化合物を含む、請求項1~25のいずれか1項に記載の方法。
- 前記微生物を培養する培地が、糖類、コハク酸、2-オキソグルタル酸およびグリセロールからなる群から選択される少なくとも1種の炭素源を含む、請求項1~26のいずれか1項に記載の方法。
- 前記微生物を、フェルラ酸、p-クマル酸からなる群から選択される少なくとも1種の誘導物質を含む培地で培養する、請求項1~27のいずれか1項に記載の方法。
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WO2020230718A1 (ja) | 2019-05-10 | 2020-11-19 | 東レ株式会社 | 3-ヒドロキシアジピン酸、α-ヒドロムコン酸および/またはアジピン酸を生産するための遺伝子改変微生物および当該化学品の製造方法 |
WO2020230719A1 (ja) | 2019-05-10 | 2020-11-19 | 東レ株式会社 | 3-ヒドロキシアジピン酸、α-ヒドロムコン酸および/またはアジピン酸を生産するための遺伝子改変微生物および当該化学品の製造方法 |
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WO2023182322A1 (ja) * | 2022-03-23 | 2023-09-28 | 東レ株式会社 | 3-ヒドロキシアジピン酸および/または3-オキソアジピン酸を生産するための遺伝子改変微生物および当該化学品の製造方法 |
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WO2023182322A1 (ja) * | 2022-03-23 | 2023-09-28 | 東レ株式会社 | 3-ヒドロキシアジピン酸および/または3-オキソアジピン酸を生産するための遺伝子改変微生物および当該化学品の製造方法 |
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EP3388525A4 (en) | 2019-08-07 |
US11753662B2 (en) | 2023-09-12 |
US10858678B2 (en) | 2020-12-08 |
EP3388525B1 (en) | 2020-09-16 |
JP7029652B2 (ja) | 2022-03-04 |
CA3007743A1 (en) | 2017-06-15 |
JPWO2017099209A1 (ja) | 2018-09-27 |
CN108368524B (zh) | 2022-05-06 |
EP3388525A1 (en) | 2018-10-17 |
US20180355385A1 (en) | 2018-12-13 |
US20210047662A1 (en) | 2021-02-18 |
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