JP5481497B2 - メチルメルカプタンとジメチルスルフィドの混合物を使用してメチオニン生産能を増加させる方法 - Google Patents
メチルメルカプタンとジメチルスルフィドの混合物を使用してメチオニン生産能を増加させる方法 Download PDFInfo
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- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 title claims description 182
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 title claims description 153
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 title claims description 105
- 229930182817 methionine Natural products 0.000 title claims description 78
- 238000000034 method Methods 0.000 title claims description 28
- 238000004519 manufacturing process Methods 0.000 title claims description 25
- 230000001965 increasing effect Effects 0.000 title description 11
- 239000000203 mixture Substances 0.000 title description 7
- 239000000243 solution Substances 0.000 claims description 66
- 238000006243 chemical reaction Methods 0.000 claims description 62
- 108090000790 Enzymes Proteins 0.000 claims description 36
- 102000004190 Enzymes Human genes 0.000 claims description 36
- FCXZBWSIAGGPCB-YFKPBYRVSA-N O-acetyl-L-homoserine Chemical compound CC(=O)OCC[C@H]([NH3+])C([O-])=O FCXZBWSIAGGPCB-YFKPBYRVSA-N 0.000 claims description 31
- GNISQJGXJIDKDJ-YFKPBYRVSA-N O-succinyl-L-homoserine Chemical compound OC(=O)[C@@H](N)CCOC(=O)CCC(O)=O GNISQJGXJIDKDJ-YFKPBYRVSA-N 0.000 claims description 28
- 238000002156 mixing Methods 0.000 claims description 18
- 239000002243 precursor Substances 0.000 claims description 16
- 108010061618 O-succinylhomoserine (thiol)-lyase Proteins 0.000 claims description 13
- 239000011259 mixed solution Substances 0.000 claims description 11
- XHXXWWGGXFUMAJ-UHFFFAOYSA-N methanethiol;sodium Chemical compound [Na].SC XHXXWWGGXFUMAJ-UHFFFAOYSA-N 0.000 claims description 8
- 238000003756 stirring Methods 0.000 claims description 7
- 101710083973 Homocysteine synthase Proteins 0.000 claims description 4
- 238000001914 filtration Methods 0.000 claims description 4
- 239000000843 powder Substances 0.000 claims description 2
- 238000001035 drying Methods 0.000 claims 1
- 239000000706 filtrate Substances 0.000 claims 1
- 125000001360 methionine group Chemical group N[C@@H](CCSC)C(=O)* 0.000 claims 1
- 229960004452 methionine Drugs 0.000 description 90
- FFEARJCKVFRZRR-UHFFFAOYSA-N L-Methionine Natural products CSCCC(N)C(O)=O FFEARJCKVFRZRR-UHFFFAOYSA-N 0.000 description 28
- 229930195722 L-methionine Natural products 0.000 description 28
- 230000000694 effects Effects 0.000 description 14
- 239000000758 substrate Substances 0.000 description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 238000000855 fermentation Methods 0.000 description 11
- 230000004151 fermentation Effects 0.000 description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- NGVDGCNFYWLIFO-UHFFFAOYSA-N pyridoxal 5'-phosphate Chemical compound CC1=NC=C(COP(O)(O)=O)C(C=O)=C1O NGVDGCNFYWLIFO-UHFFFAOYSA-N 0.000 description 9
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 8
- 235000007682 pyridoxal 5'-phosphate Nutrition 0.000 description 6
- 239000011589 pyridoxal 5'-phosphate Substances 0.000 description 6
- 230000000813 microbial effect Effects 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- 241000588879 Chromobacterium violaceum Species 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 230000002255 enzymatic effect Effects 0.000 description 4
- 238000006911 enzymatic reaction Methods 0.000 description 4
- 238000004128 high performance liquid chromatography Methods 0.000 description 4
- 150000007524 organic acids Chemical class 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 230000009257 reactivity Effects 0.000 description 4
- 235000011121 sodium hydroxide Nutrition 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 239000001384 succinic acid Substances 0.000 description 4
- 241001619535 Hyphomonas neptunium Species 0.000 description 3
- MEFKEPWMEQBLKI-AIRLBKTGSA-N S-adenosyl-L-methioninate Chemical compound O[C@@H]1[C@H](O)[C@@H](C[S+](CC[C@H](N)C([O-])=O)C)O[C@H]1N1C2=NC=NC(N)=C2N=C1 MEFKEPWMEQBLKI-AIRLBKTGSA-N 0.000 description 3
- 229960001570 ademetionine Drugs 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000010276 construction Methods 0.000 description 3
- 238000010799 enzyme reaction rate Methods 0.000 description 3
- 235000013373 food additive Nutrition 0.000 description 3
- 239000002778 food additive Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- 229960001327 pyridoxal phosphate Drugs 0.000 description 3
- UKAUYVFTDYCKQA-UHFFFAOYSA-N -2-Amino-4-hydroxybutanoic acid Natural products OC(=O)C(N)CCO UKAUYVFTDYCKQA-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 241000588881 Chromobacterium Species 0.000 description 2
- 241000588724 Escherichia coli Species 0.000 description 2
- 241001302584 Escherichia coli str. K-12 substr. W3110 Species 0.000 description 2
- UKAUYVFTDYCKQA-VKHMYHEASA-N L-homoserine Chemical compound OC(=O)[C@@H](N)CCO UKAUYVFTDYCKQA-VKHMYHEASA-N 0.000 description 2
- 241001533218 Methylococcus sp. Species 0.000 description 2
- 241000589516 Pseudomonas Species 0.000 description 2
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 2
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 2
- 239000003674 animal food additive Substances 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- CVSVTCORWBXHQV-UHFFFAOYSA-N creatine Chemical compound NC(=[NH2+])N(C)CC([O-])=O CVSVTCORWBXHQV-UHFFFAOYSA-N 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 239000008363 phosphate buffer Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 2
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 description 2
- 150000003568 thioethers Chemical class 0.000 description 2
- UJLGQABYUGGBAP-WCCKRBBISA-N (2s)-2-amino-4-methylsulfanylbutanoic acid;methanethiol Chemical compound SC.CSCC[C@H](N)C(O)=O UJLGQABYUGGBAP-WCCKRBBISA-N 0.000 description 1
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
- ANWQCUUQZSYYND-UHFFFAOYSA-N 5-(2-methylsulfanylethyl)imidazolidine-2,4-dione Chemical compound CSCCC1C(NC(N1)=O)=O.CSCCC1C(NC(N1)=O)=O ANWQCUUQZSYYND-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 1
- 241000194110 Bacillus sp. (in: Bacteria) Species 0.000 description 1
- 241000589171 Bradyrhizobium sp. Species 0.000 description 1
- 241000941525 Chromobacterium sp. Species 0.000 description 1
- 241000186249 Corynebacterium sp. Species 0.000 description 1
- 241000488157 Escherichia sp. Species 0.000 description 1
- 241000233866 Fungi Species 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
- 206010061218 Inflammation Diseases 0.000 description 1
- XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 description 1
- 241000589902 Leptospira Species 0.000 description 1
- 241001148629 Leptospira meyeri Species 0.000 description 1
- 241000589924 Leptospira sp. Species 0.000 description 1
- 241000557267 Methylobacillus sp. Species 0.000 description 1
- 208000000112 Myalgia Diseases 0.000 description 1
- 241000143395 Nitrosomonas sp. Species 0.000 description 1
- 241001503673 Nocardia farcinica Species 0.000 description 1
- 108700027408 O-acetylhomoserine (thiol)-lyase Proteins 0.000 description 1
- 241000589776 Pseudomonas putida Species 0.000 description 1
- 241000589774 Pseudomonas sp. Species 0.000 description 1
- 241000607149 Salmonella sp. Species 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 229960001138 acetylsalicylic acid Drugs 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 210000001367 artery Anatomy 0.000 description 1
- 238000010170 biological method Methods 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 229960001231 choline Drugs 0.000 description 1
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 229960003624 creatine Drugs 0.000 description 1
- 239000006046 creatine Substances 0.000 description 1
- 235000018417 cysteine Nutrition 0.000 description 1
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 235000020776 essential amino acid Nutrition 0.000 description 1
- 239000003797 essential amino acid Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 208000019423 liver disease Diseases 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 208000013465 muscle pain Diseases 0.000 description 1
- 239000002858 neurotransmitter agent Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229960005137 succinic acid Drugs 0.000 description 1
- 150000003900 succinic acid esters Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229960003080 taurine Drugs 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 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
- C12P13/00—Preparation of nitrogen-containing organic compounds
- C12P13/04—Alpha- or beta- amino acids
- C12P13/12—Methionine; Cysteine; Cystine
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- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Microbiology (AREA)
- General Chemical & Material Sciences (AREA)
- Biotechnology (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
本発明は、一つの態様として、
1)メチオニン前駆体であるO−アセチルホモセリンまたはO−スクシニルホモセリン;前記メチオニン前駆体をメチオニンに転換する転換酵素;およびメチルメルカプタンとジメチルスルフィドとの混合液を含む反応溶液を製造する段階;および、
2)前記反応溶液を攪拌しながら、酵素転換反応を行う段階を含むメチオニン生産方法を提供する。
メチルメルカプタン(CH3SH)+O−スクシニル−L−ホモセリン⇔コハク酸塩+L−メチオニン
メチルメルカプタン(CH3SH)+O−アセチル−L−ホモセリン⇔酢酸塩+L−メチオニン
実施例1の条件と同様な条件で持続的なメチオニン生成促進反応を観察するために、メチルメルカプタンとジメチルスルフィド混合液を時間に応じて持続投入しながらメチオニン生成を確認した。同一の転換反応液を用いて10分経過時ごとにそれぞれメチルメルカプタン溶液とジメチルスルフィド混合液を投入しながら30分間反応を持続した。30分後に反応を終了させ、HPLCを用いて生成されたメチオニン量を測定した。ジメチルスルフィド混合比は実施例1で最も高いメチオニン生産増加を示したメチルメルカプタン溶液とジメチルスルフィド1:0.25(mol:mol)混合を反応条件とした。結果は、下記表2に示した。
より大型の反応器で転換反応効率を確認するために、1L規模の回分式反応器で700mMのO−アセチルホモセリン500mLを使って反応を行った。メチルメルカプタン溶液あるいはメチルメルカプタン溶液とジメチルスルフィド1:0.25(mol:mol)で混合された混合液を3.0mL/minの流量で60分間連続的に供給しながら酵素転換反応を行った。各溶液に含まれたメチルメルカプタン量は同一になるように調節した。反応温度は33℃、攪拌は700rpmに設定した。転換酵素液は、前記の実施例と同様な方法で製造して10mL投入し、酵素補助因子であるピリドキサールホスフェート(pyridoxal 5'-phosphate)は、0.1mM濃度で投入した。約3時間後に生成されたメチオニンの量をHPLCを用いて測定した。その結果を下記表3に示した。
メチオニンへの酵素転換反応にO−アセチルホモセリンの他にO−スクシニルホモセリンを基質として使用してメチオニンとコハク酸が生成される反応を行った。
Claims (8)
- (i) メチオニン前駆体であるO−アセチルホモセリンまたはO−スクシニルホモセリン、(ii) 前記メチオニン前駆体をメチオニンに転換する転換酵素、および (iii) メチルメルカプタンとジメチルスルフィドの混合液、を含む反応溶液を製造する第1の段階、ならびに
前記反応溶液を攪拌しながら、酵素転換反応を行う第2の段階を含み、
前記メチオニン転換酵素は、シスタチオニンγシンターゼ(cystathionine gamma synthase)、O−スクシニルホモセリンスルフヒドリラーゼ(O-succinylhomoserine sulfhydrylase)およびO−アセチルホモセリンスルフヒドリラーゼ(O-acetylhomoserine sulfhydrylase)からなる群から選択される1種以上である、メチオニン生産方法。 - 前記メチルメルカプタンは、メチルメルカプタンガスまたはメチルメルカプタンナトリウム溶液の形態で供給される請求項1に記載のメチオニン生産方法。
- 前記メチルメルカプタンとジメチルスルフィドの混合比率は、メチルメルカプタン:ジメチルスルフィドが1:0.05〜1:1のモル比率である請求項1に記載のメチオニン生産方法。
- 前記メチルメルカプタンとジメチルスルフィドの混合比率は、メチルメルカプタン:ジメチルスルフィドが1:0.20〜1:1のモル比率である請求項3に記載のメチオニン生産方法。
- 前記メチルメルカプタンとジメチルスルフィドの混合比率は、メチルメルカプタン:ジメチルスルフィドが1:0.25〜1:0.5のモル比率である請求項4に記載のメチオニン生産方法。
- 前記方法は、酵素転換反応を終了する段階を更に含む請求項1に記載のメチオニン生産方法。
- 前記方法は、前記酵素転換反応によって形成された反応液に存在するメチオニンを精製する段階を更に含む請求項1に記載のメチオニン生産方法。
- 前記メチオニンを精製する方法は、1)酵素転換反応液から菌体を分離する段階、2)前記菌体が分離した反応液を脱色およびろ過する段階、および3)メチオニンの粉末形態を得るために、前記ろ過液を乾燥する段階を含む請求項7に記載のメチオニン生産方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
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KR10-2009-0016604 | 2009-02-27 | ||
KR1020090016604A KR101048593B1 (ko) | 2009-02-27 | 2009-02-27 | 메칠머캅탄과 디메칠설파이드의 혼합물을 사용하여 메치오닌 생산능을 증가시키는 방법 |
PCT/KR2010/001250 WO2010098629A2 (ko) | 2009-02-27 | 2010-02-26 | 메칠머캅탄과 디메칠설파이드의 혼합물을 사용하여 메치오닌 생산능을 증가시키는 방법 |
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JP2012518432A JP2012518432A (ja) | 2012-08-16 |
JP5481497B2 true JP5481497B2 (ja) | 2014-04-23 |
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Country Status (10)
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US (1) | US9024063B2 (ja) |
EP (1) | EP2402453B1 (ja) |
JP (1) | JP5481497B2 (ja) |
KR (1) | KR101048593B1 (ja) |
CN (1) | CN102333881B (ja) |
DK (1) | DK2402453T3 (ja) |
ES (1) | ES2618407T3 (ja) |
MY (1) | MY152999A (ja) |
PL (1) | PL2402453T3 (ja) |
WO (1) | WO2010098629A2 (ja) |
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KR101250651B1 (ko) | 2010-12-21 | 2013-04-03 | 씨제이제일제당 (주) | 신규 o-아세틸호모세린 설피드릴라제 또는 변이체 및 이를 이용한 메치오닌 전환 방법 |
BR112013016810B1 (pt) | 2010-12-29 | 2020-12-29 | Cj Cheiljedang Corporation | métodos para produção de l-metionina e produtos correlatos |
CN107475319A (zh) * | 2011-09-02 | 2017-12-15 | 阿克马法国公司 | L‑甲硫氨酸的制备方法 |
FR3041658B1 (fr) * | 2015-09-30 | 2017-10-20 | Arkema France | Procede de production de l-methionine |
WO2017065529A1 (ko) | 2015-10-13 | 2017-04-20 | 씨제이제일제당 (주) | O-아세틸호모세린 설피드릴라제 변이체 및 이를 이용한 l-메치오닌 제조 방법 |
PL3380627T3 (pl) * | 2015-11-27 | 2020-01-31 | Evonik Degussa Gmbh | Sposób wytwarzania L-metioniny |
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KR102221040B1 (ko) | 2019-05-09 | 2021-03-03 | 씨제이제일제당 주식회사 | L-아미노산을 생산하는 미생물 및 이를 이용한 l-아미노산을 생산하는 방법 |
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US2775616A (en) * | 1956-12-25 | Preparation of methionine from a-aming- | ||
KR100651220B1 (ko) * | 2004-06-29 | 2006-11-29 | 씨제이 주식회사 | L-메씨오닌 생산 균주 및 상기 균주를 이용한l-메씨오닌의 생산방법 |
JP2009501548A (ja) | 2005-07-18 | 2009-01-22 | ビーエーエスエフ ソシエタス・ヨーロピア | 微生物におけるメチオニン生産のためのジメチルジスルフィドの使用 |
JP2009504172A (ja) * | 2005-08-18 | 2009-02-05 | ビーエーエスエフ ソシエタス・ヨーロピア | 向上したメチオニン合成効率を有する微生物 |
KR100905381B1 (ko) * | 2006-07-28 | 2009-06-30 | 씨제이제일제당 (주) | L-메치오닌 전구체 생산 균주 및 상기 l-메치오닌전구체로부터의 l-메치오닌 및 유기산의 생산방법 |
ES2708988T3 (es) | 2007-02-23 | 2019-04-12 | Merck Sharp & Dohme | Anticuerpos anti-IL-23p19 obtenidos por ingeniería genética |
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US20120123158A1 (en) | 2012-05-17 |
EP2402453A2 (en) | 2012-01-04 |
KR101048593B1 (ko) | 2011-07-12 |
WO2010098629A3 (ko) | 2010-12-09 |
US9024063B2 (en) | 2015-05-05 |
WO2010098629A2 (ko) | 2010-09-02 |
ES2618407T3 (es) | 2017-06-21 |
CN102333881A (zh) | 2012-01-25 |
PL2402453T3 (pl) | 2017-09-29 |
EP2402453A4 (en) | 2013-11-20 |
KR20100097782A (ko) | 2010-09-06 |
DK2402453T3 (en) | 2017-03-13 |
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