JP2009524615A5 - - Google Patents
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- Publication number
- JP2009524615A5 JP2009524615A5 JP2008551744A JP2008551744A JP2009524615A5 JP 2009524615 A5 JP2009524615 A5 JP 2009524615A5 JP 2008551744 A JP2008551744 A JP 2008551744A JP 2008551744 A JP2008551744 A JP 2008551744A JP 2009524615 A5 JP2009524615 A5 JP 2009524615A5
- Authority
- JP
- Japan
- Prior art keywords
- homoserine
- methionine
- butyl
- methyl
- process according
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 238000000034 method Methods 0.000 claims 43
- 239000000460 chlorine Substances 0.000 claims 20
- 239000003054 catalyst Substances 0.000 claims 17
- 229910052801 chlorine Inorganic materials 0.000 claims 17
- 238000006243 chemical reaction Methods 0.000 claims 15
- UKAUYVFTDYCKQA-VKHMYHEASA-N L-homoserine Chemical compound OC(=O)[C@@H](N)CCO UKAUYVFTDYCKQA-VKHMYHEASA-N 0.000 claims 14
- 230000002378 acidificating effect Effects 0.000 claims 14
- -1 sulfonyloxy Chemical group 0.000 claims 12
- UKAUYVFTDYCKQA-UHFFFAOYSA-N -2-Amino-4-hydroxybutanoic acid Natural products OC(=O)C(N)CCO UKAUYVFTDYCKQA-UHFFFAOYSA-N 0.000 claims 11
- FFEARJCKVFRZRR-SCSAIBSYSA-N D-methionine Chemical compound CSCC[C@@H](N)C(O)=O FFEARJCKVFRZRR-SCSAIBSYSA-N 0.000 claims 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 10
- 229910052736 halogen Inorganic materials 0.000 claims 10
- 150000002367 halogens Chemical group 0.000 claims 10
- 229910052739 hydrogen Inorganic materials 0.000 claims 10
- 229960004452 methionine Drugs 0.000 claims 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 10
- UKAUYVFTDYCKQA-GSVOUGTGSA-N D-homoserine Chemical compound OC(=O)[C@H](N)CCO UKAUYVFTDYCKQA-GSVOUGTGSA-N 0.000 claims 9
- 239000003513 alkali Substances 0.000 claims 9
- 229930182818 D-methionine Natural products 0.000 claims 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 8
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 claims 7
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 6
- 239000002585 base Substances 0.000 claims 6
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims 6
- 229910052794 bromium Inorganic materials 0.000 claims 6
- 230000006315 carbonylation Effects 0.000 claims 6
- 238000005810 carbonylation reaction Methods 0.000 claims 6
- 239000003795 chemical substances by application Substances 0.000 claims 6
- 229910052731 fluorine Inorganic materials 0.000 claims 6
- 239000001257 hydrogen Substances 0.000 claims 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 6
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 6
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims 6
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 6
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 5
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims 5
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 5
- 229910052792 caesium Inorganic materials 0.000 claims 5
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 claims 5
- 229910052744 lithium Inorganic materials 0.000 claims 5
- 239000000203 mixture Substances 0.000 claims 5
- 229910052700 potassium Inorganic materials 0.000 claims 5
- 239000011591 potassium Substances 0.000 claims 5
- 229910052701 rubidium Inorganic materials 0.000 claims 5
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical group [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 claims 5
- 229910052708 sodium Inorganic materials 0.000 claims 5
- 239000011734 sodium Substances 0.000 claims 5
- 239000000126 substance Substances 0.000 claims 5
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical group CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 claims 4
- 229910019142 PO4 Inorganic materials 0.000 claims 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims 4
- 239000002253 acid Substances 0.000 claims 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims 4
- 150000001875 compounds Chemical class 0.000 claims 4
- 239000011968 lewis acid catalyst Substances 0.000 claims 4
- 229930182817 methionine Natural products 0.000 claims 4
- 239000003960 organic solvent Substances 0.000 claims 4
- 239000010452 phosphate Substances 0.000 claims 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 4
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims 3
- 239000007848 Bronsted acid Substances 0.000 claims 3
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims 3
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 3
- 229910052788 barium Inorganic materials 0.000 claims 3
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 claims 3
- 229910052791 calcium Inorganic materials 0.000 claims 3
- 239000011575 calcium Substances 0.000 claims 3
- 229910052740 iodine Inorganic materials 0.000 claims 3
- 229910052749 magnesium Inorganic materials 0.000 claims 3
- 239000011777 magnesium Substances 0.000 claims 3
- 229920000137 polyphosphoric acid Polymers 0.000 claims 3
- QIGAOWQMYKZVTO-UHFFFAOYSA-N 1,1,2,4,4,5,7,7,8,8,8-undecafluoro-5-(trifluoromethyl)oct-1-ene-3,6-dione Chemical compound FC(F)=C(F)C(=O)C(F)(F)C(F)(C(F)(F)F)C(=O)C(F)(F)C(F)(F)F QIGAOWQMYKZVTO-UHFFFAOYSA-N 0.000 claims 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 2
- FFEARJCKVFRZRR-UHFFFAOYSA-N L-Methionine Natural products CSCCC(N)C(O)=O FFEARJCKVFRZRR-UHFFFAOYSA-N 0.000 claims 2
- 229930195722 L-methionine Natural products 0.000 claims 2
- 229920000557 Nafion® Polymers 0.000 claims 2
- 229910021536 Zeolite Inorganic materials 0.000 claims 2
- 230000003796 beauty Effects 0.000 claims 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 229920001577 copolymer Polymers 0.000 claims 2
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 claims 2
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims 2
- 238000000855 fermentation Methods 0.000 claims 2
- 230000004151 fermentation Effects 0.000 claims 2
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 claims 2
- 230000007062 hydrolysis Effects 0.000 claims 2
- 238000006460 hydrolysis reaction Methods 0.000 claims 2
- 239000011630 iodine Substances 0.000 claims 2
- 229910052901 montmorillonite Inorganic materials 0.000 claims 2
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims 2
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 claims 2
- 239000000725 suspension Substances 0.000 claims 2
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 claims 2
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 claims 2
- 239000010457 zeolite Substances 0.000 claims 2
- ZPKLHZSTXKNUST-VKHMYHEASA-N (2s)-2-(carbamoylamino)-4-hydroxybutanoic acid Chemical compound NC(=O)N[C@H](C(O)=O)CCO ZPKLHZSTXKNUST-VKHMYHEASA-N 0.000 claims 1
- KYVBNYUBXIEUFW-UHFFFAOYSA-N 1,1,3,3-tetramethylguanidine Chemical compound CN(C)C(=N)N(C)C KYVBNYUBXIEUFW-UHFFFAOYSA-N 0.000 claims 1
- DSGXRCPUXCXBIE-UHFFFAOYSA-N 1-(2-methylsulfanylethyl)imidazolidine-2,4-dione Chemical compound CSCCN1CC(=O)NC1=O DSGXRCPUXCXBIE-UHFFFAOYSA-N 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 1
- 241000894006 Bacteria Species 0.000 claims 1
- 241000186216 Corynebacterium Species 0.000 claims 1
- 241000588722 Escherichia Species 0.000 claims 1
- 239000002841 Lewis acid Substances 0.000 claims 1
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 claims 1
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims 1
- 230000010933 acylation Effects 0.000 claims 1
- 238000005917 acylation reaction Methods 0.000 claims 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 claims 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 claims 1
- ZRALSGWEFCBTJO-UHFFFAOYSA-N anhydrous guanidine Natural products NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims 1
- 125000002619 bicyclic group Chemical group 0.000 claims 1
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- 239000006184 cosolvent Substances 0.000 claims 1
- 238000012258 culturing Methods 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 239000012973 diazabicyclooctane Substances 0.000 claims 1
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims 1
- 239000001963 growth medium Substances 0.000 claims 1
- QJPWUUJVYOJNMH-UHFFFAOYSA-N homoserine lactone Chemical compound NC1CCOC1=O QJPWUUJVYOJNMH-UHFFFAOYSA-N 0.000 claims 1
- 230000006698 induction Effects 0.000 claims 1
- 150000002500 ions Chemical class 0.000 claims 1
- 150000002596 lactones Chemical class 0.000 claims 1
- 150000007517 lewis acids Chemical class 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 244000005700 microbiome Species 0.000 claims 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 claims 1
- 239000011347 resin Substances 0.000 claims 1
- 229920005989 resin Polymers 0.000 claims 1
- 238000006798 ring closing metathesis reaction Methods 0.000 claims 1
- 238000007363 ring formation reaction Methods 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 239000012265 solid product Substances 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- 150000003512 tertiary amines Chemical class 0.000 claims 1
- 150000005622 tetraalkylammonium hydroxides Chemical class 0.000 claims 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 claims 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 claims 1
- 125000004385 trihaloalkyl group Chemical group 0.000 claims 1
- GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical group [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 claims 1
- 0 *CCCC(C(O)=O)NCC(*)=O Chemical compound *CCCC(C(O)=O)NCC(*)=O 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102006004063.5 | 2006-01-28 | ||
| DE102006004063A DE102006004063A1 (de) | 2006-01-28 | 2006-01-28 | Verfahren zur Herstellung von Methionin aus Homoserin |
| PCT/EP2007/050082 WO2007085514A2 (de) | 2006-01-28 | 2007-01-04 | Verfahren zur herstellung von methionin aus homoserin |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2009524615A JP2009524615A (ja) | 2009-07-02 |
| JP2009524615A5 true JP2009524615A5 (enExample) | 2010-02-25 |
| JP5383203B2 JP5383203B2 (ja) | 2014-01-08 |
Family
ID=37771916
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2008551744A Expired - Fee Related JP5383203B2 (ja) | 2006-01-28 | 2007-01-04 | ホモセリンからのメチオニンの製法 |
Country Status (9)
| Country | Link |
|---|---|
| US (2) | US7368600B2 (enExample) |
| EP (1) | EP1976827B1 (enExample) |
| JP (1) | JP5383203B2 (enExample) |
| CN (1) | CN101374806B (enExample) |
| BR (1) | BRPI0707299A2 (enExample) |
| CA (1) | CA2640523A1 (enExample) |
| DE (1) | DE102006004063A1 (enExample) |
| RU (1) | RU2472778C2 (enExample) |
| WO (1) | WO2007085514A2 (enExample) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101565379B (zh) * | 2009-06-11 | 2012-02-01 | 浙江雅迪纤维有限公司 | L-高丝氨酸盐酸盐的制备方法 |
| IN2012KN02804A (enExample) * | 2010-03-09 | 2015-05-01 | Novus Int Inc | |
| JP2011231103A (ja) * | 2010-04-06 | 2011-11-17 | Sumitomo Chemical Co Ltd | 含硫アミノ酸の製造方法 |
| JP2012184213A (ja) * | 2010-04-06 | 2012-09-27 | Sumitomo Chemical Co Ltd | 含硫アミノ酸の製造方法 |
| JP2012184215A (ja) * | 2010-06-01 | 2012-09-27 | Sumitomo Chemical Co Ltd | メチオニンの製造方法 |
| FR2965561B1 (fr) * | 2010-10-05 | 2012-08-31 | Adisseo France Sas | Procede de preparation d?un acide amine a partir de 2-aminobutyrolactone |
| US9834491B2 (en) | 2013-03-20 | 2017-12-05 | Cj Cheiljedang Corporation | Method for producing bio-based homoserine lactone and bio-based organic acid from O-acyl homoserine produced by microorganisms |
| WO2015141886A1 (ko) * | 2014-03-20 | 2015-09-24 | 씨제이제일제당(주) | 미생물 유래의 o-아실호모세린으로부터 바이오 유래 호모세린락톤 염산염 및 바이오 유래 유기산을 제조하는 방법 |
| KR101632483B1 (ko) | 2014-04-11 | 2016-06-22 | 씨제이제일제당 (주) | 호모세린계 화합물의 처리 공정 |
| CN104531577B (zh) * | 2014-12-19 | 2017-05-17 | 浙江工业大学 | 嗜烟碱节杆菌wyg001及其在制备n‑boc‑l‑高丝氨酸内酯中的应用 |
| CN108291243A (zh) * | 2015-11-27 | 2018-07-17 | 赢创德固赛有限公司 | 生产l-甲硫氨酸的方法 |
| ES2803208T3 (es) | 2015-12-17 | 2021-01-25 | Evonik Operations Gmbh | Una célula acetogénica genéticamente modificada |
| MY187786A (en) | 2016-07-27 | 2021-10-22 | Evonik Operations Gmbh | N-acetyl homoserine |
| KR102582675B1 (ko) * | 2019-01-11 | 2023-09-25 | 씨제이제일제당 주식회사 | 글루포시네이트 제조 방법 |
| CN110204517A (zh) * | 2019-07-12 | 2019-09-06 | 利尔化学股份有限公司 | 一种(s)-(2-氧代四氢呋喃-3-基)氨基甲酸酯的制备方法 |
| KR102286950B1 (ko) * | 2019-09-10 | 2021-08-06 | 씨제이제일제당 주식회사 | L-호모세린 제조 방법 |
| CN110683976A (zh) * | 2019-11-04 | 2020-01-14 | 济源市万洋华康生物科技有限公司 | 一种制备(r)-硒甲基硒代半胱氨酸的方法 |
| KR20250155045A (ko) * | 2023-03-01 | 2025-10-29 | 후난 라이어 바이오테크 씨오., 엘티디. | L-호모세린으로부터 직접적으로 l-메티오닌을 제조하는 공정 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2397628A (en) | 1942-08-21 | 1946-04-02 | Merck & Co Inc | Synthesis of amino acids |
| GB651165A (en) * | 1947-07-15 | 1951-03-14 | Gustav Bischoff | Improvements in or relating to the preparation of ª†-methyl-mercapto-ª‡-aminobutyricacid |
| GB978593A (en) | 1960-09-12 | 1964-12-23 | Kyowa Hakko Kogyo Company Ltd | Method for producing l-homoserine by fermentation |
| CH525863A (de) | 1967-09-12 | 1972-07-31 | Kyowa Hakko Kogyo Kk | Verfahren zur Herstellung von L-Homoserin und L-Lysin |
| JPS5024306B2 (enExample) * | 1972-01-22 | 1975-08-14 | ||
| JPS60258158A (ja) * | 1984-06-05 | 1985-12-20 | Showa Denko Kk | システイン誘導体の製造方法 |
| DE3432307A1 (de) * | 1984-09-03 | 1986-04-10 | Boehringer Ingelheim KG, 6507 Ingelheim | Aminosaeurederivate, verfahren zu ihrer herstellung und pharmazeutische zusammensetzungen |
| DE3930534A1 (de) | 1989-09-13 | 1991-03-21 | Degussa | Verfahren zur herstellung von acrolein durch katalytische gasphasenoxidation von propen |
| JP2592724B2 (ja) * | 1991-04-30 | 1997-03-19 | 日本ペイント株式会社 | 反応射出成形用ポリウレア樹脂組成物 |
| DE19547236A1 (de) | 1995-12-18 | 1997-07-03 | Degussa | Verfahren zur Herstellung von D,L-Methionin oder dessen Salz |
| RU2144564C1 (ru) | 1998-10-13 | 2000-01-20 | Закрытое акционерное общество "Научно-исследовательский институт Аджиномото-Генетика" | ФРАГМЕНТ ДНК rhtB, КОДИРУЮЩИЙ СИНТЕЗ БЕЛКА RhtB, ПРИДАЮЩЕГО УСТОЙЧИВОСТЬ К L-ГОМОСЕРИНУ БАКТЕРИЯМ ESCHERICHIA COLI, И СПОСОБ ПОЛУЧЕНИЯ L-АМИНОКИСЛОТ |
| JP2001002668A (ja) * | 1999-06-18 | 2001-01-09 | Mitsubishi Chemicals Corp | ホモセリンラクトンの製造方法 |
| RU2212447C2 (ru) | 2000-04-26 | 2003-09-20 | Закрытое акционерное общество "Научно-исследовательский институт Аджиномото-Генетика" | Штамм escherichia coli - продуцент аминокислоты (варианты) и способ получения аминокислот (варианты) |
| US20020155556A1 (en) | 2000-12-22 | 2002-10-24 | Ajinomoto Co., Inc | Method of producing target substance by fermentation |
| DK1511724T3 (da) * | 2002-05-24 | 2014-06-16 | Bayer Cropscience Ag | Fremgangsmåde til fremstilling af thioalkylaminderivater |
| DE10239082A1 (de) | 2002-08-26 | 2004-03-04 | Basf Ag | Verfahren zur fermentativen Herstellung schwefelhaltiger Feinchemikalien |
| DE10359668A1 (de) | 2003-12-18 | 2005-07-14 | Basf Ag | Verfahren zur Herstellung von Methionin |
-
2006
- 2006-01-28 DE DE102006004063A patent/DE102006004063A1/de not_active Withdrawn
-
2007
- 2007-01-04 JP JP2008551744A patent/JP5383203B2/ja not_active Expired - Fee Related
- 2007-01-04 WO PCT/EP2007/050082 patent/WO2007085514A2/de not_active Ceased
- 2007-01-04 EP EP07703642.4A patent/EP1976827B1/de not_active Not-in-force
- 2007-01-04 RU RU2008134625/04A patent/RU2472778C2/ru not_active IP Right Cessation
- 2007-01-04 CN CN2007800036942A patent/CN101374806B/zh not_active Expired - Fee Related
- 2007-01-04 CA CA002640523A patent/CA2640523A1/en not_active Abandoned
- 2007-01-04 BR BRPI0707299-6A patent/BRPI0707299A2/pt not_active IP Right Cessation
- 2007-01-25 US US11/657,534 patent/US7368600B2/en not_active Expired - Fee Related
-
2008
- 2008-02-13 US US12/068,951 patent/US7884240B2/en not_active Expired - Fee Related
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