KR102076532B1 - 2-케토 카르복실산의 제조 방법 - Google Patents
2-케토 카르복실산의 제조 방법 Download PDFInfo
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- KR102076532B1 KR102076532B1 KR1020177030286A KR20177030286A KR102076532B1 KR 102076532 B1 KR102076532 B1 KR 102076532B1 KR 1020177030286 A KR1020177030286 A KR 1020177030286A KR 20177030286 A KR20177030286 A KR 20177030286A KR 102076532 B1 KR102076532 B1 KR 102076532B1
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- South Korea
- Prior art keywords
- salt
- acid
- culture broth
- ion exchange
- carboxylic acid
- Prior art date
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- 238000000034 method Methods 0.000 title claims description 38
- 238000002360 preparation method Methods 0.000 title description 4
- 150000003839 salts Chemical class 0.000 claims abstract description 31
- 238000000855 fermentation Methods 0.000 claims abstract description 18
- 230000004151 fermentation Effects 0.000 claims abstract description 18
- 244000005700 microbiome Species 0.000 claims abstract description 13
- 239000001963 growth medium Substances 0.000 claims abstract description 12
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 5
- QHKABHOOEWYVLI-UHFFFAOYSA-N 3-methyl-2-oxobutanoic acid Chemical compound CC(C)C(=O)C(O)=O QHKABHOOEWYVLI-UHFFFAOYSA-N 0.000 claims description 33
- 108090000623 proteins and genes Proteins 0.000 claims description 27
- 238000004821 distillation Methods 0.000 claims description 24
- 229920005989 resin Polymers 0.000 claims description 20
- 239000011347 resin Substances 0.000 claims description 20
- 238000005342 ion exchange Methods 0.000 claims description 19
- 150000001413 amino acids Chemical class 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 9
- 241000186226 Corynebacterium glutamicum Species 0.000 claims description 8
- LCTONWCANYUPML-UHFFFAOYSA-M Pyruvate Chemical compound CC(=O)C([O-])=O LCTONWCANYUPML-UHFFFAOYSA-M 0.000 claims description 7
- 125000000129 anionic group Chemical group 0.000 claims description 7
- 101100125907 Streptomyces coelicolor (strain ATCC BAA-471 / A3(2) / M145) ilvC1 gene Proteins 0.000 claims description 6
- 101150015189 aceE gene Proteins 0.000 claims description 6
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- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims 1
- 230000001376 precipitating effect Effects 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 15
- 239000000047 product Substances 0.000 description 12
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- 238000006243 chemical reaction Methods 0.000 description 6
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- 239000006228 supernatant Substances 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- BKAJNAXTPSGJCU-UHFFFAOYSA-N 4-methyl-2-oxopentanoic acid Chemical compound CC(C)CC(=O)C(O)=O BKAJNAXTPSGJCU-UHFFFAOYSA-N 0.000 description 5
- 101150105723 ilvD1 gene Proteins 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 241000283690 Bos taurus Species 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 229940070710 valerate Drugs 0.000 description 4
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 4
- NJMGRJLQRLFQQX-HYXAFXHYSA-N 2-isopropylmaleic acid Chemical compound CC(C)C(\C(O)=O)=C\C(O)=O NJMGRJLQRLFQQX-HYXAFXHYSA-N 0.000 description 3
- JVQYSWDUAOAHFM-UHFFFAOYSA-N 3-methyl-2-oxovaleric acid Chemical compound CCC(C)C(=O)C(O)=O JVQYSWDUAOAHFM-UHFFFAOYSA-N 0.000 description 3
- 108010064711 Homoserine dehydrogenase Proteins 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
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- 238000004458 analytical method Methods 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
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- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 239000002243 precursor Substances 0.000 description 3
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- 108020004652 Aspartate-Semialdehyde Dehydrogenase Proteins 0.000 description 2
- 241000193830 Bacillus <bacterium> Species 0.000 description 2
- 241000186146 Brevibacterium Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 2
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- 108010053763 Pyruvate Carboxylase Proteins 0.000 description 2
- 102100039895 Pyruvate carboxylase, mitochondrial Human genes 0.000 description 2
- 241000187747 Streptomyces Species 0.000 description 2
- 102000006843 Threonine synthase Human genes 0.000 description 2
- 108010022394 Threonine synthase Proteins 0.000 description 2
- ZSLZBFCDCINBPY-ZSJPKINUSA-N acetyl-CoA Chemical compound O[C@@H]1[C@H](OP(O)(O)=O)[C@@H](COP(O)(=O)OP(O)(=O)OCC(C)(C)[C@@H](O)C(=O)NCCC(=O)NCCSC(=O)C)O[C@H]1N1C2=NC=NC(N)=C2N=C1 ZSLZBFCDCINBPY-ZSJPKINUSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 235000004279 alanine Nutrition 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 108010071598 homoserine kinase Proteins 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 101150053253 pgi gene Proteins 0.000 description 2
- 235000018102 proteins Nutrition 0.000 description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 238000001256 steam distillation Methods 0.000 description 2
- 125000000542 sulfonic acid group Chemical group 0.000 description 2
- 108010037084 valine-pyruvate transaminase Proteins 0.000 description 2
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
- KPGXRSRHYNQIFN-UHFFFAOYSA-N 2-oxoglutaric acid Chemical compound OC(=O)CCC(=O)C(O)=O KPGXRSRHYNQIFN-UHFFFAOYSA-N 0.000 description 1
- 108010028984 3-isopropylmalate dehydratase Proteins 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 102100036475 Alanine aminotransferase 1 Human genes 0.000 description 1
- 108010082126 Alanine transaminase Proteins 0.000 description 1
- 108010003415 Aspartate Aminotransferases Proteins 0.000 description 1
- 102000004625 Aspartate Aminotransferases Human genes 0.000 description 1
- 102100036608 Aspartate aminotransferase, cytoplasmic Human genes 0.000 description 1
- 108010055400 Aspartate kinase Proteins 0.000 description 1
- 108030002081 Aspartate transaminases Proteins 0.000 description 1
- 101100489185 Bacillus subtilis (strain 168) yugH gene Proteins 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- GSXOAOHZAIYLCY-UHFFFAOYSA-N D-F6P Natural products OCC(=O)C(O)C(O)C(O)COP(O)(O)=O GSXOAOHZAIYLCY-UHFFFAOYSA-N 0.000 description 1
- NBSCHQHZLSJFNQ-GASJEMHNSA-N D-Glucose 6-phosphate Chemical compound OC1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H](O)[C@H]1O NBSCHQHZLSJFNQ-GASJEMHNSA-N 0.000 description 1
- -1 EC 2.7 .2.4) Proteins 0.000 description 1
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- 102000004190 Enzymes Human genes 0.000 description 1
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- 241000588724 Escherichia coli Species 0.000 description 1
- 101100493587 Escherichia coli (strain K12) avtA gene Proteins 0.000 description 1
- VFRROHXSMXFLSN-UHFFFAOYSA-N Glc6P Natural products OP(=O)(O)OCC(O)C(O)C(O)C(O)C=O VFRROHXSMXFLSN-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 108090001042 Hydro-Lyases Proteins 0.000 description 1
- 102000004867 Hydro-Lyases Human genes 0.000 description 1
- 108090000769 Isomerases Proteins 0.000 description 1
- 102000004195 Isomerases Human genes 0.000 description 1
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
- 238000008214 LDL Cholesterol Methods 0.000 description 1
- 208000001647 Renal Insufficiency Diseases 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 108010006873 Threonine Dehydratase Proteins 0.000 description 1
- 102100033451 Thyroid hormone receptor beta Human genes 0.000 description 1
- GBXZONVFWYCRPT-JGWLITMVSA-N [(2r,3s,4r,5r)-3,4,5,6-tetrahydroxy-1-oxohexan-2-yl] dihydrogen phosphate Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](C=O)OP(O)(O)=O GBXZONVFWYCRPT-JGWLITMVSA-N 0.000 description 1
- 150000001412 amines Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 101150065474 avtA gene Proteins 0.000 description 1
- BGWGXPAPYGQALX-ARQDHWQXSA-N beta-D-fructofuranose 6-phosphate Chemical compound OC[C@@]1(O)O[C@H](COP(O)(O)=O)[C@@H](O)[C@@H]1O BGWGXPAPYGQALX-ARQDHWQXSA-N 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 235000013681 dietary sucrose Nutrition 0.000 description 1
- 235000015872 dietary supplement Nutrition 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- IZRVEUZYBVGCFC-UHFFFAOYSA-N ethyl 2-hydroxyisovalerate Chemical compound CCOC(=O)C(O)C(C)C IZRVEUZYBVGCFC-UHFFFAOYSA-N 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- GXOGLXKLKOVKEA-UHFFFAOYSA-N formyl pentanoate Chemical compound CCCCC(=O)OC=O GXOGLXKLKOVKEA-UHFFFAOYSA-N 0.000 description 1
- 230000002538 fungal effect Effects 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 229930195712 glutamate Natural products 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 101150095957 ilvA gene Proteins 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000004715 keto acids Chemical class 0.000 description 1
- 201000006370 kidney failure Diseases 0.000 description 1
- 101150087199 leuA gene Proteins 0.000 description 1
- 101150025049 leuB gene Proteins 0.000 description 1
- WQVJUBFKFCDYDQ-BBWFWOEESA-N leubethanol Natural products C1=C(C)C=C2[C@H]([C@H](CCC=C(C)C)C)CC[C@@H](C)C2=C1O WQVJUBFKFCDYDQ-BBWFWOEESA-N 0.000 description 1
- 101150035025 lysC gene Proteins 0.000 description 1
- 230000037353 metabolic pathway Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 108010038467 pyruvate quinone oxidoreductase Proteins 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000010188 recombinant method Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229960004793 sucrose Drugs 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 101150072448 thrB gene Proteins 0.000 description 1
- 101150000850 thrC gene Proteins 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C12P7/44—Polycarboxylic acids
- C12P7/50—Polycarboxylic acids having keto groups, e.g. 2-ketoglutaric acid
-
- 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
- C12P7/24—Preparation of oxygen-containing organic compounds containing a carbonyl group
- C12P7/26—Ketones
-
- 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
- C12N15/11—DNA or RNA fragments; Modified forms thereof; Non-coding nucleic acids having a biological activity
- C12N15/52—Genes encoding for enzymes or proenzymes
-
- 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
-
- C12R1/15—
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12R—INDEXING SCHEME ASSOCIATED WITH SUBCLASSES C12C - C12Q, RELATING TO MICROORGANISMS
- C12R2001/00—Microorganisms ; Processes using microorganisms
- C12R2001/01—Bacteria or Actinomycetales ; using bacteria or Actinomycetales
- C12R2001/15—Corynebacterium
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S435/00—Chemistry: molecular biology and microbiology
- Y10S435/8215—Microorganisms
- Y10S435/822—Microorganisms using bacteria or actinomycetales
- Y10S435/843—Corynebacterium
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Genetics & Genomics (AREA)
- Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biotechnology (AREA)
- General Engineering & Computer Science (AREA)
- Microbiology (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biomedical Technology (AREA)
- Molecular Biology (AREA)
- Physics & Mathematics (AREA)
- Biophysics (AREA)
- Plant Pathology (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Micro-Organisms Or Cultivation Processes Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP09162079 | 2009-06-05 | ||
| EP09162079.9 | 2009-06-05 | ||
| PCT/EP2010/056345 WO2010139527A2 (en) | 2009-06-05 | 2010-05-10 | A method for the preparation of 2-keto carboxylic acid |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020117028941A Division KR20120036821A (ko) | 2009-06-05 | 2010-05-10 | 2-케토 카르복실산의 제조 방법 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR20170121313A KR20170121313A (ko) | 2017-11-01 |
| KR102076532B1 true KR102076532B1 (ko) | 2020-02-13 |
Family
ID=43016582
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020177030286A Active KR102076532B1 (ko) | 2009-06-05 | 2010-05-10 | 2-케토 카르복실산의 제조 방법 |
| KR1020117028941A Ceased KR20120036821A (ko) | 2009-06-05 | 2010-05-10 | 2-케토 카르복실산의 제조 방법 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020117028941A Ceased KR20120036821A (ko) | 2009-06-05 | 2010-05-10 | 2-케토 카르복실산의 제조 방법 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US9879289B2 (enExample) |
| EP (1) | EP2438181A2 (enExample) |
| JP (1) | JP5882202B2 (enExample) |
| KR (2) | KR102076532B1 (enExample) |
| CN (1) | CN102459621B (enExample) |
| BR (1) | BRPI1012007A2 (enExample) |
| WO (1) | WO2010139527A2 (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BR112014021439B1 (pt) | 2012-04-27 | 2021-12-21 | Evonik Technochemie Gmbh | Polipeptídeo de isopropilmalato sintase e a sequência de nucleotídeos que o codifica, vetor, microrganismo do gênero corynebacterium e uso do mesmo, bem como processo fermentativo para a produção de kic ou l-leucina |
| ES2623161T3 (es) | 2013-06-03 | 2017-07-10 | Evonik Degussa Gmbh | Procedimiento para la preparación de L-valina utilizando corinebacterias recombinantes que contienen el operón ilvBN inducible por propionato |
| WO2018063424A1 (en) * | 2016-09-30 | 2018-04-05 | Dow Global Technologies Llc | Processes to prepare elongated 2-ketoacids and c-5-c10 compounds therefrom via genetic modifications to microbial metabolic pathways |
| WO2020161228A1 (en) * | 2019-02-08 | 2020-08-13 | Basf Se | Process for producing 4,4`-dichlorodiphenyl sulfoxide |
| KR102344689B1 (ko) * | 2020-09-01 | 2021-12-29 | 씨제이제일제당 주식회사 | L-발린 생산 미생물 및 이를 이용한 l-발린 생산 방법 |
| CN114507127A (zh) * | 2020-11-17 | 2022-05-17 | 中国科学院上海高等研究院 | 一种2-酮基泛解酸的合成方法 |
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| WO2006082252A2 (en) * | 2005-02-07 | 2006-08-10 | Metabolic Explorer | Method for the enzymatic production of alpha-ketobutyrate |
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|---|---|---|---|---|
| JPS52108086A (en) * | 1976-03-08 | 1977-09-10 | Ajinomoto Co Inc | Preparation of alpha-keto-acid |
| JPS5542550A (en) * | 1978-09-22 | 1980-03-25 | Nippon Kayaku Co Ltd | Production of alpha-ketoacid |
| KR20010041516A (ko) * | 1998-03-02 | 2001-05-25 | 미시간 바이오테크놀로지 인스티튜트 | 음이온 교환 크로마토그래피를 사용한 유기산의 정제 |
| DE19907567B4 (de) | 1999-02-22 | 2007-08-09 | Forschungszentrum Jülich GmbH | Verfahren zur mikrobiellen Herstellung von L-Valin |
| US6288275B1 (en) * | 1999-07-09 | 2001-09-11 | Henkel Corporation | Separation and purification of carboxylic acids from fermentation broths |
| CA2470978A1 (en) * | 2002-01-03 | 2003-07-24 | A.E. Staley Manufacturing Co. | Process for purifying an organic acid |
| DE10212322A1 (de) * | 2002-03-20 | 2003-10-02 | Degussa | Herstellung von Alkalisalzen von alpha-Ketoncarbonsäuren |
| DE102005045301A1 (de) * | 2005-09-22 | 2007-04-05 | Degussa Ag | Verfahren zur Herstellung von organisch-chemischen Verbindungen unter Verwendung coryneformer Bakterien |
| DE102007016715A1 (de) | 2007-04-04 | 2008-10-09 | Evonik Degussa Gmbh | Nahrungsergänzungsmittel enthaltend alpha-Ketosäuren |
| DE102009016119A1 (de) | 2009-04-03 | 2010-10-14 | Evonik Degussa Gmbh | Nahrungsergänzungsmittel enthaltend alpha-Ketosäuren zur Unterstützung der Diabetestherapie |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| WO2006082252A2 (en) * | 2005-02-07 | 2006-08-10 | Metabolic Explorer | Method for the enzymatic production of alpha-ketobutyrate |
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|---|---|
| CN102459621A (zh) | 2012-05-16 |
| US20120065428A1 (en) | 2012-03-15 |
| JP2012528577A (ja) | 2012-11-15 |
| KR20170121313A (ko) | 2017-11-01 |
| WO2010139527A3 (en) | 2011-03-03 |
| BRPI1012007A2 (pt) | 2015-09-22 |
| US9879289B2 (en) | 2018-01-30 |
| JP5882202B2 (ja) | 2016-03-09 |
| CN102459621B (zh) | 2015-01-28 |
| KR20120036821A (ko) | 2012-04-18 |
| EP2438181A2 (en) | 2012-04-11 |
| WO2010139527A2 (en) | 2010-12-09 |
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