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WO2017074063A1 - Procédé de production d'un acide aminocarboxylique à chaîne lourde - Google Patents

Procédé de production d'un acide aminocarboxylique à chaîne lourde Download PDF

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Publication number
WO2017074063A1
WO2017074063A1 PCT/KR2016/012172 KR2016012172W WO2017074063A1 WO 2017074063 A1 WO2017074063 A1 WO 2017074063A1 KR 2016012172 W KR2016012172 W KR 2016012172W WO 2017074063 A1 WO2017074063 A1 WO 2017074063A1
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gene
heavy chain
acid
recombinant microorganism
aminocarboxylic acid
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English (en)
Korean (ko)
Inventor
안정오
이홍원
박규연
장민정
전우영
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Korea Research Institute of Bioscience and Biotechnology KRIBB
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Korea Research Institute of Bioscience and Biotechnology KRIBB
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Priority to JP2018522065A priority Critical patent/JP7164112B2/ja
Priority to CN201680076062.8A priority patent/CN108473993A/zh
Priority to EP16860246.4A priority patent/EP3375880B1/fr
Priority to US15/771,812 priority patent/US20180327724A1/en
Priority claimed from KR1020160141019A external-priority patent/KR101903553B1/ko
Publication of WO2017074063A1 publication Critical patent/WO2017074063A1/fr
Anticipated expiration legal-status Critical
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    • 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
    • C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
    • C12N9/10—Transferases (2.)
    • 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
    • C12N15/70—Vectors or expression systems specially adapted for E. coli
    • 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
    • C12N15/79—Vectors or expression systems specially adapted for eukaryotic hosts
    • C12N15/80—Vectors or expression systems specially adapted for eukaryotic hosts for fungi
    • C12N15/81—Vectors or expression systems specially adapted for eukaryotic hosts for fungi for yeasts
    • 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
    • C12P13/00—Preparation of nitrogen-containing organic compounds
    • 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
    • C12P7/64—Fats; Fatty oils; Ester-type waxes; Higher fatty acids, i.e. having at least seven carbon atoms in an unbroken chain bound to a carboxyl group; Oxidised oils or fats

Definitions

  • the present invention relates to a method for producing heavy chain aminocarboxylic acids, and more particularly, to remove the fat aldehyde dehydrogenase gene and ⁇ -oxidation metabolic pathway related genes in the ⁇ -oxidation metabolic pathway,
  • the present invention relates to a method for producing heavy chain aminocarboxylic acid from fatty acids by culturing a recombinant microorganism into which a transaminase gene has been introduced.
  • Bioplatform compounds are produced through biological or chemical conversion based on biomass-derived raw materials, and are used for synthesis of polymer monomers and new materials.
  • Heavy-chain aminocarboxylic acids in the bioplatform compounds are used as monomers of polyamides, and the polyamides are classified into aliphatic polyamides, aromatic polyamides, and aliphatic ring polyamides.
  • Typical examples of the aliphatic polyamides include nylon 12, nylon 6, nylon 66, and the like, and aromatic polyamides are known under the name aramid by introducing an aromatic skeleton to further improve heat resistance.
  • Nylon is a representative engineering plastic material, and since 1940, its demand and use have been steadily increasing due to high crystallinity, mechanical strength, thermal stability, and excellent wear / friction resistance, and improve the thermal and mechanical properties of nylon. Research in various fields has been ongoing. Among them, research has been made to impregnate wax and graphite to improve wear resistance of nylon, and in addition, studies on improving physical properties by polymer crosslinking are being conducted.
  • nylon 12 synthesized by the polycondensation method of 12-aminododecanic acid has a low specific gravity, excellent low temperature characteristics and abrasion resistance, and strong weather resistance due to the low influence of ultraviolet rays, and other nylon resins (nylon 6).
  • Heavy chain aminocarboxylic acids such as 12-aminododecanoic acid
  • Production of heavy chain aminocarboxylic acids can be achieved by biological methods through chemical synthesis or microbial fermentation, which requires the development of new strains using metabolic engineering and optimization of fermentation processes. .
  • microorganisms having a ⁇ -oxidative metabolic pathway and an ⁇ -oxidative metabolic pathway can be used as a strain capable of producing heavy chain aminocarboxylic acid.
  • a method of producing ⁇ -aminododecanoic acid from E. coli is known. (US2010 / 0324257 A1).
  • the heavy chain aminocarboxylic acid is prepared by further introducing a process of transferring an amine group to the heavy chain aldehyde carboxylic acid, there is a problem that the yield is not high in the production of the heavy chain aminocarboxylic acid using the microorganism.
  • the present invention provides a method for removing fatty acid from a fatty acid by culturing the recombinant microorganism and the recombinant microorganism in which the fat aldehyde dehydrogenase gene and the ⁇ -oxidative metabolic pathway related gene in the ⁇ -oxidation metabolic pathway are removed, and the ⁇ -transaminase gene is introduced. It is an object to provide a method for producing heavy chain aminocarboxylic acids.
  • the present invention provides a recombinant microorganism in which the fat aldehyde dehydrogenase gene and the ⁇ -oxidation metabolic pathway related gene in the ⁇ -oxidation metabolic pathway are removed, and the ⁇ -transaminase gene is introduced. do.
  • the fatty aldehyde dehydrogenase and ⁇ -oxidation metabolic pathway related genes are preferably but not limited to all homologous genes present in the microorganism. According to another embodiment of the present invention, the fatty aldehyde dehydrogenase and ⁇ -oxidation pathway related genes are preferably but not limited to some homologous genes present in the microorganism.
  • the fatty aldehyde dehydrogenase gene may be a gene selected from the group consisting of FALDH1, FALDH2, FALDH3 and FALDH4 gene, but is not limited thereto.
  • the ⁇ -oxidation pathway related gene may be an acyl-CoA oxidase gene, but is not limited thereto.
  • the acyl-CoA oxidase gene may be selected from the group consisting of ACO1, ACO2, ACO3, ACO4, ACO5 and ACO6 genes, but is not limited thereto.
  • the microorganism may be yeast or E. coli, but is not limited thereto.
  • the yeast is composed of Yarrowia sp., Saccharomyces sp., Pichia sp., And Candida sp. Yeast selected from the group may be, but is not limited thereto.
  • the yeast of the genus Yarrowia may be Yarrowia lipolytica, but is not limited thereto.
  • the present invention comprises the steps of preparing a recombinant microorganism wherein the fat aldehyde dehydrogenase gene and ⁇ -oxidation metabolic pathway related genes in the ⁇ -oxidation metabolic pathway is removed, and the ⁇ -transaminase gene is introduced; And (2) provides a method for producing a heavy chain aminocarboxylic acid comprising the step of culturing the substrate to the recombinant microorganism.
  • the substrate may be a fatty acid, but is not limited thereto.
  • the fatty acid and heavy chain aminocarboxylic acid may have 5 to 30 carbon atoms, preferably 6 to 20 carbon atoms, more preferably 8 to 16 carbon atoms, but is not limited thereto.
  • the fatty acid may be dodecanoic acid, but is not limited thereto.
  • the heavy chain aminocarboxylic acid may be 12-aminododecanoic acid, but is not limited thereto.
  • the recombinant microorganism of the present invention is a heavy chain aminocarboxylic acid from a substrate such as fatty acid by removing the fat aldehyde dehydrogenase gene and ⁇ -oxidation metabolic pathway related genes in the ⁇ -oxidation metabolic pathway, and also the ⁇ -transaminase gene is introduced.
  • a substrate such as fatty acid
  • 12-aminododecanoic acid which is a raw material of nylon 12 can be produced in high yield.
  • Figure 2 schematically shows the preparation of recombinant microorganisms in which the fat aldehyde dehydrogenase gene and the ⁇ -oxidation metabolic pathway gene related to ⁇ -oxidation have been removed and the ⁇ -transaminase gene has been introduced.
  • Figure 3 schematically shows a vector having a ura3 gene to be used as a selection marker for gene knockout for strain improvement and a pop-out for removing the ura3 gene after the knockout cassette insertion.
  • Figure 4 is a schematic diagram showing the manufacturing process of the knock-out cassette used in the production of the transformed microorganism of the present invention.
  • Figure 5 schematically shows a transformation vector containing the ⁇ -transaminase gene for strain improvement.
  • Figure 6 is a graph showing the types of genes knocked out and transduced in the transformed microorganism of the present invention.
  • Figure 7 is a graph showing the amount of heavy chain aminocarboxylic acid produced from the dodecanoic acid substrate of the transforming microorganism of the present invention.
  • FIG. 8 is a graph showing the amount of heavy chain aminocarboxylic acid produced from dodecanoic acid as a substrate when the Y2-36 strain of the present invention is cultured in a flask.
  • the present invention provides a recombinant microorganism in which the fat aldehyde dehydrogenase gene and the ⁇ -oxidation metabolic pathway related gene in the ⁇ -oxidation metabolic pathway have been removed, and the ⁇ -transaminase gene has been introduced. .
  • ⁇ -oxidation refers to a metabolic process in which a methyl group terminal of a fatty acid is oxidized to form a dicarboxylic acid
  • ⁇ -oxidation means that a ⁇ -site carbon atom is oxidized in a carboxy group. It is a metabolic process that releases acetyl CoA and gradually breaks down into fatty acids with two carbon atoms each time.
  • the concepts of ⁇ -oxidation and ⁇ -oxidation and the enzymes involved in this metabolic process are well known to those skilled in the biochemistry art.
  • ⁇ -hydroxy fatty acid is first produced by the action of cytochrome P450 and NADPH-cytochrome P450 reductase, and the ⁇ -hydroxy fatty acid is ⁇ -aldehyde fatty acid is produced by the action of fatty alcohol dehydrogenase and fatty alcohol oxidase, and the ⁇ -aldehyde fatty acid is produced by the action of fatty aldehyde dehydrogenase.
  • acyl-CoA oxidase produces fatty acids having two carbon atoms (see FIG. 1).
  • Transaminase (TA, EC 2.6.1.X) is an enzyme that exists widely in nature and is involved in the transfer of amine groups in the nitrogen metabolism of organisms. In general, transaminase removes the amino group of one amino acid and transfers it to another ⁇ -keto acid. Transaminase is used for the production of optically pure non-natural amino acids and amine compounds due to its many advantages such as broad substrate specificity, high optical selectivity, fast reaction rate, excellent stability, and the need for coenzyme reproduction. have.
  • Transaminase can be divided into five groups based on the structure and multiple sequence alignments of proteins in the Pfam database, including ⁇ -amino acids: pyruvate transaminase, ornithine transaminase, 4 Transaminases belonging to group III containing aminobutyrate transaminase and the like are called ⁇ -transaminases. Unlike conventional transaminase, ⁇ -transaminase transfers an amine group of an amino acid with an amine group at a non-alpha position or an amine compound without a carboxyl group to an amine receptor such as 2-ketoglutarate or pyruvate. Perform.
  • ⁇ -transaminase can be used as an enzyme which is very useful for the production of optically active amine compounds.
  • ⁇ -transaminase was first used by Celgene Co. of the United States to synthesize chiral amines for the first time in 1990. Recently, studies on asymmetric synthesis of chiral amines and improved kinetic resolution have been made. This is an important part of the study, and 12-oxolauric acid methyl ester was prepared by Evonik, Germany, in 2012 using ⁇ -transaminase of Chromobacterium violaceum DSM30191 strain. Examples of conversion to aminolauric acid methyl ester are also known.
  • the fatty aldehyde dehydrogenase gene is preferably all homologous genes present in the microorganism is removed, but in some cases, the recombinant microorganism from which some of the genes are removed Can be applied.
  • the fatty aldehyde dehydrogenase gene may be selected from the group consisting of FALDH1, FALDH2, FALDH3 and FALDH4 gene, but is not limited thereto.
  • the FALDH1, FALDH2, FALDH3 and FALDH4 genes may include, but are not limited to, nucleotide sequences consisting of SEQ ID NO: 1 and SEQ ID NO: 4, respectively.
  • the ⁇ -oxidation metabolic pathway-related gene is preferably all homologous genes present in the microorganism is removed, but in some cases, the recombinant microorganism from which some of the genes are removed Can be applied.
  • the ⁇ -oxidation pathway related gene is an acyl-CoA oxidase gene, and the acyl-CoA oxidase gene may be selected from the group consisting of ACO1, ACO2, ACO3, ACO4, ACO5 and ACO6 genes, but is not limited thereto. No (see Figure 2).
  • the ACO1, ACO2, ACO3, ACO4, ACO5 and ACO6 gene may include a base sequence consisting of SEQ ID NO: 5 and SEQ ID NO: 10, but is not limited thereto.
  • the ⁇ -transaminase gene may include a nucleotide sequence consisting of SEQ ID NO: 11, but is not limited thereto.
  • recombination in which the fat aldehyde dehydrogenase gene and ⁇ -oxidation metabolic pathway related genes are removed using a conventional gene recombination technique known in the art, and a ⁇ -transaminase gene is introduced.
  • Microorganisms can be produced.
  • the term "removal" is not only a part or all of the gene is physically removed, but also a state in which a protein is not made from mRNA transcribed from the gene and the protein expressed from the gene function The state of not being able to be used is also used in the sense of comprehensive inclusion.
  • introduction is used in the sense that encompasses both when the gene is inserted into the genome of the microorganism, or when the gene is expressed without inserting the gene into the genome of the microorganism.
  • Genetic recombination techniques that can be used include, but are not limited to, methods such as transformation, transduction, transfection, microinjection, electroporation, and the like. .
  • any microorganism that can be used may be used without limitation any microorganism having both ⁇ -oxidation and ⁇ -oxidation metabolic processes, for example, eukaryotes including yeast and prokaryotes including E. coli are used. Can be.
  • the microorganism is preferably using yeast, and yeasts such as Yarrowia genus, Saccharomyces genus, Pichia genus, Candida genus and the like may be used without limitation.
  • Yarrowia Lipolitica Candida tropicalis, Candida infanticola, Saccharomyces cerevisiae, Pichia alcoholophia or Candida mycoderma ( Candida mycoderma) is preferred, and Yarrowia lipolitica is more preferred.
  • the cytochrome P450 and NADPH-cytochrome P450 are supplied when the fatty acid is supplied to the substrate.
  • the alcohol is oxidized to form an aldehyde by the action of fatty alcohol dehydrogenase and fatty alcohol oxidase, but the fatty aldehyde dehydroge Since nados is removed, no further oxidation occurs.
  • the fatty acid aldehyde thus formed is aminated by the action of ⁇ -transaminase to form aminocarboxylic acid.
  • the fat aldehyde dehydrogenase gene and the ⁇ -oxidation metabolic pathway related gene in the ⁇ -oxidation metabolic pathway are removed, and further the addition of fatty acid aldehyde using a recombinant microorganism into which the ⁇ -transaminase gene has been introduced.
  • the heavy chain aminocarboxylic acid can be produced in high yield by preventing oxidation and ⁇ -oxidation metabolism and also introducing an amine group into the heavy chain aldehyde fatty acid.
  • the fatty aldehyde dehydrogenase and ⁇ -oxidation pathway related genes are preferably all homologous genes present in the microorganism, but in some cases, the recombinant microorganism from which some of the genes have been removed may also be applied in the present invention. Can be.
  • any microorganism that can be used may be used without limitation any microorganism having both ⁇ -oxidation and ⁇ -oxidation metabolic processes, for example, eukaryotes including yeast and prokaryotes including E. coli are used. Can be.
  • the microorganism is preferably using yeast, and yeasts such as Yarrowia genus, Saccharomyces genus, Pichia genus, Candida genus and the like may be used without limitation.
  • Yarrowia Lipolitica Candida Tropicalis, Candida Infantica, Saccharomyces cerevisiae, Pichia alcoholopia or Candida Mycoderma, and more preferably Yarrowia lipolitica. desirable.
  • recombination in which the fat aldehyde dehydrogenase gene and ⁇ -oxidation metabolic pathway related genes are removed using a conventional gene recombination technique known in the art, and a ⁇ -transaminase gene is introduced.
  • Microorganisms can be produced.
  • the term "removal” is not only a part or all of the gene is physically removed, but also a state in which a protein is not made from mRNA transcribed from the gene and the protein expressed from the gene function The state of not being able to be used is also used in the sense of comprehensive inclusion.
  • introduction is used in the sense that encompasses both when the gene is inserted into the genome of the microorganism, or when the gene is expressed without inserting the gene into the genome of the microorganism.
  • heavy chain aminocarboxylic acid is used to mean all heavy chain aminocarboxylic acids having 5 to 30 carbon atoms, preferably 8 to 16 carbon atoms.
  • the heavy chain aminocarboxylic acid is preferably 12-aminododecanoic acid having 12 carbon atoms, but is not limited thereto.
  • the substrate of step (2) may be a fatty acid, but is not limited thereto.
  • the fatty acid may be a fatty acid having 5 to 30 carbon atoms, preferably 8 to 16 carbon atoms, more preferably dodecanoic acid having 12 carbon atoms, but is not limited thereto.
  • a vector having a ura3 gene to be used as a selection marker for gene knock-out for strain improvement and a pop-out for removing the ura3 gene after insertion of the knock-out cassette was constructed (FIG. 3).
  • the primers used to PCR the pop-out region and ura3 in two pieces are shown in Table 3.
  • Fat aldehyde dehydrogenase gene and ⁇ -oxidation metabolic pathway in the ⁇ -oxidation metabolism pathway present in wild type Yarrowia strain using the knock-out cassette prepared in Example 1 and the transduction vector prepared in Example 2 A total of eight knock-out strains were constructed in which some or all of the related genes were removed and the ⁇ -transaminase gene was introduced (FIG. 6). Specifically, strains to knock-out or introduce genes were plated on YPD plates and incubated at 30 ° C. for 16-24 hours.
  • the cultured cells were scraped with a loop and vortexed in 100 ⁇ l of one-step buffer (45% PEG4000, 100 mM DTT, 0.1 L LiAc, 25 ⁇ g single-strand carrier DNA), followed by knock-out cassette and transduction vector (1 ng). Above) was added and vortexed again, and incubated at 39 ° C. for 1 hour.
  • the cultured samples were loaded into selection medium (YNB w / o amino acid 6.7g / L, Glucose 20g / L) and incubated at 30 ° C. for 48 hours to select the inserted strain. Then, it was confirmed by PCR using the fries included in the gene deletion of Table 2 to confirm that the cassettes are correctly inserted on the genome of the selected strain.
  • the strain into which the cassette was inserted went through a pop-out process to proceed with the insertion of another cassette.
  • 200 ⁇ l of the culture medium was mixed with 5 ′ FOA medium (YNB w / o amino acid 6.7g / L, Glucose 20g / L, 5 'FOA).
  • 5 ′ FOA medium YNB w / o amino acid 6.7g / L, Glucose 20g / L, 5 'FOA.
  • the strain to be tested was inoculated in 2 ml of YPD medium (Bacto Laboratories, Yeast extract 10g / L, peptone 20g / L, glucose 20g / L) the day before at 30 °C, 200rpm.
  • 2 ml of growth stage medium (pH 6.0) having the composition shown in Table 7 was placed in a 24-well plate, and then inoculated with 1% of the precultured culture, and then incubated at 30 ° C. and 450 rpm for one day in a plate stirrer.
  • the Y1-11 strain which only knocked out the ⁇ -oxidation metabolism related gene, was unable to produce 12-aminododecanoic acid from the substrate dodecanoic acid, but the fat aldehyde dehydrogenase gene was further knocked out.
  • the Y2-36 strain showed a 12-aminododecanoic acid synthesis capacity of about 8 mg / L when cultured in a flask (FIG. 8).
  • a sample analysis experiment using the Y2-36 strain was performed.
  • Example 4 100 ⁇ l of 6N sulfuric acid was added to 500 ⁇ l of the culture medium of the Y2-36 strain that showed the highest ability to synthesize 12-aminododecanoic acid, and then methanol 500 containing 10% toluene and 2.2% hydrochloric acid for methylation reaction. ⁇ l was added and the methylation reaction was carried out at 100 ° C. for 1 hour. 100 ⁇ l of 10N sodium hydroxide and 500 ⁇ l of diethyl ether were added to the reaction solution, followed by sufficient vortexing, followed by centrifugation at 12,000 rpm for 2 minutes. Thereafter, only the solvent layer was separated, and GC / MS analysis was performed under the following analysis conditions.
  • the recombinant Y2-36 strain of the present invention can synthesize 12-aminododecanoic acid from the substrate dodecanoic acid (FIG. 9).

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Abstract

La présente invention concerne un procédé de production d'un acide aminocarboxylique à chaîne lourde, et plus particulièrement, un micro-organisme recombiné dans lequel un gène de l'aldéhyde gras déshydrogénase dans la voie du métabolisme ω-oxydatif et un gène lié à la voie du métabolisme β-oxydatif sont éliminés et un gène de la ω-transaminase est introduit, et un procédé de production d'un acide aminocarboxylique à chaîne lourde par culture du micro-organisme recombiné. Le micro-organisme recombiné selon la présente invention peut empêcher la poursuite de l'oxydation de l'aldéhyde gras et du métabolisme β-oxydatif et produire un acide aminocarboxylique, tel qu'un 12-aminodécane, à titre de matière première du Nylon 12, à partir d'un substrat tel qu'un acide gras à un rendement élevé par introduction d'un groupe amine à son extrémité terminale.
PCT/KR2016/012172 2015-10-27 2016-10-27 Procédé de production d'un acide aminocarboxylique à chaîne lourde Ceased WO2017074063A1 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
JP2018522065A JP7164112B2 (ja) 2015-10-27 2016-10-27 重鎖アミノカルボン酸の生産方法
CN201680076062.8A CN108473993A (zh) 2015-10-27 2016-10-27 中链氨基羧酸的生产方法
EP16860246.4A EP3375880B1 (fr) 2015-10-27 2016-10-27 Procédé de production d'un acide aminocarboxylique à chaîne lourde
US15/771,812 US20180327724A1 (en) 2015-10-27 2016-10-27 Method for producing heavy chain aminocarboxylic acid

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KR10-2015-0149254 2015-10-27
KR20150149254 2015-10-27
KR10-2016-0141019 2016-10-27
KR1020160141019A KR101903553B1 (ko) 2015-10-27 2016-10-27 중쇄 아미노카르복시산의 생산 방법

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2025189391A1 (fr) * 2024-03-13 2025-09-18 中国科学院深圳先进技术研究院 Bactérie ingénierisée pour inhiber la synthèse d'acide dodécanedioïque, son procédé de construction et son utilisation

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JP2006271378A (ja) * 2005-03-04 2006-10-12 Ube Ind Ltd １２−アミノドデカン酸の製造方法及びその製造方法に使用する生体触媒
KR101145405B1 (ko) * 2008-12-03 2012-05-16 한국생명공학연구원 글리세롤 산화경로가 차단된 １、３―프로판디올 생산 변이체
US8530206B2 (en) * 2008-05-21 2013-09-10 Ecover Coordination Center N.V. Method for the production of medium-chain sophorolipids
US9012227B2 (en) * 2007-12-17 2015-04-21 Evonik Degussa Gmbh ω-Aminocarboxylic acids, ω-aminocarboxylic acid esters, or recombinant cells which produce lactams thereof

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2006271378A (ja) * 2005-03-04 2006-10-12 Ube Ind Ltd １２−アミノドデカン酸の製造方法及びその製造方法に使用する生体触媒
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