BRPI0707299A2 - método para produzir metionina a partir de homosserina - Google Patents
método para produzir metionina a partir de homosserina Download PDFInfo
- Publication number
- BRPI0707299A2 BRPI0707299A2 BRPI0707299-6A BRPI0707299A BRPI0707299A2 BR PI0707299 A2 BRPI0707299 A2 BR PI0707299A2 BR PI0707299 A BRPI0707299 A BR PI0707299A BR PI0707299 A2 BRPI0707299 A2 BR PI0707299A2
- Authority
- BR
- Brazil
- Prior art keywords
- acid
- formula
- methionine
- butyl
- methyl
- Prior art date
Links
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 title claims abstract description 86
- UKAUYVFTDYCKQA-VKHMYHEASA-N L-homoserine Chemical compound OC(=O)[C@@H](N)CCO UKAUYVFTDYCKQA-VKHMYHEASA-N 0.000 title claims abstract description 65
- 229930182817 methionine Natural products 0.000 title claims abstract description 42
- UKAUYVFTDYCKQA-UHFFFAOYSA-N -2-Amino-4-hydroxybutanoic acid Natural products OC(=O)C(N)CCO UKAUYVFTDYCKQA-UHFFFAOYSA-N 0.000 title claims abstract description 31
- 238000000034 method Methods 0.000 title claims description 110
- 229960004452 methionine Drugs 0.000 claims abstract description 92
- 238000006243 chemical reaction Methods 0.000 claims abstract description 66
- FFEARJCKVFRZRR-UHFFFAOYSA-N L-Methionine Natural products CSCCC(N)C(O)=O FFEARJCKVFRZRR-UHFFFAOYSA-N 0.000 claims abstract description 53
- 229930195722 L-methionine Natural products 0.000 claims abstract description 46
- 238000004519 manufacturing process Methods 0.000 claims abstract description 27
- UKAUYVFTDYCKQA-GSVOUGTGSA-N D-homoserine Chemical compound OC(=O)[C@H](N)CCO UKAUYVFTDYCKQA-GSVOUGTGSA-N 0.000 claims abstract description 25
- FFEARJCKVFRZRR-SCSAIBSYSA-N D-methionine Chemical compound CSCC[C@@H](N)C(O)=O FFEARJCKVFRZRR-SCSAIBSYSA-N 0.000 claims abstract description 22
- 229930182818 D-methionine Natural products 0.000 claims abstract description 22
- 239000002253 acid Substances 0.000 claims description 56
- -1 2-methylthioethyl Chemical group 0.000 claims description 45
- 239000003377 acid catalyst Substances 0.000 claims description 40
- 229910052783 alkali metal Inorganic materials 0.000 claims description 40
- 150000001340 alkali metals Chemical class 0.000 claims description 39
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 38
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 30
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 29
- 238000000855 fermentation Methods 0.000 claims description 28
- 230000004151 fermentation Effects 0.000 claims description 28
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 25
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 24
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 24
- 239000003054 catalyst Substances 0.000 claims description 24
- 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 description 20
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 20
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 20
- 229910052736 halogen Inorganic materials 0.000 claims description 20
- 150000002367 halogens Chemical group 0.000 claims description 20
- 229910052744 lithium Inorganic materials 0.000 claims description 20
- 229910052700 potassium Inorganic materials 0.000 claims description 20
- 239000011591 potassium Substances 0.000 claims description 20
- 229910052701 rubidium Inorganic materials 0.000 claims description 20
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 claims description 20
- 229910052708 sodium Inorganic materials 0.000 claims description 20
- 239000011734 sodium Substances 0.000 claims description 20
- 229910052792 caesium Inorganic materials 0.000 claims description 19
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 claims description 19
- 239000000203 mixture Substances 0.000 claims description 19
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 19
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 19
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 18
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 18
- 239000000460 chlorine Substances 0.000 claims description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 18
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 17
- 229910052801 chlorine Inorganic materials 0.000 claims description 17
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 16
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 16
- 235000011149 sulphuric acid Nutrition 0.000 claims description 16
- 239000003960 organic solvent Substances 0.000 claims description 15
- 229920000137 polyphosphoric acid Polymers 0.000 claims description 15
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 15
- 150000001875 compounds Chemical class 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 13
- 239000011968 lewis acid catalyst Substances 0.000 claims description 13
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 13
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 claims description 12
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 12
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims description 12
- 229920000557 Nafion® Polymers 0.000 claims description 12
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 12
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 12
- 235000011007 phosphoric acid Nutrition 0.000 claims description 12
- 239000000243 solution Substances 0.000 claims description 12
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 12
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 claims description 12
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 claims description 12
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 11
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 11
- 229910052794 bromium Inorganic materials 0.000 claims description 11
- 239000003795 chemical substances by application Substances 0.000 claims description 11
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 10
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 claims description 10
- 239000002841 Lewis acid Substances 0.000 claims description 10
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 10
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 10
- 150000001733 carboxylic acid esters Chemical class 0.000 claims description 10
- 150000002576 ketones Chemical class 0.000 claims description 10
- 150000007517 lewis acids Chemical class 0.000 claims description 10
- 125000004385 trihaloalkyl group Chemical group 0.000 claims description 10
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical group [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 9
- 150000003857 carboxamides Chemical class 0.000 claims description 9
- 229920001577 copolymer Polymers 0.000 claims description 9
- 238000006460 hydrolysis reaction Methods 0.000 claims description 9
- 239000011347 resin Substances 0.000 claims description 9
- 229920005989 resin Polymers 0.000 claims description 9
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 8
- KOPBYBDAPCDYFK-UHFFFAOYSA-N Cs2O Inorganic materials [O-2].[Cs+].[Cs+] KOPBYBDAPCDYFK-UHFFFAOYSA-N 0.000 claims description 8
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 8
- 230000006181 N-acylation Effects 0.000 claims description 8
- 229910019142 PO4 Inorganic materials 0.000 claims description 8
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 8
- 150000007513 acids Chemical class 0.000 claims description 8
- 150000001298 alcohols Chemical class 0.000 claims description 8
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 8
- 229910052788 barium Inorganic materials 0.000 claims description 8
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 claims description 8
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 claims description 8
- 229910052791 calcium Inorganic materials 0.000 claims description 8
- 239000011575 calcium Substances 0.000 claims description 8
- AKUNKIJLSDQFLS-UHFFFAOYSA-M dicesium;hydroxide Chemical compound [OH-].[Cs+].[Cs+] AKUNKIJLSDQFLS-UHFFFAOYSA-M 0.000 claims description 8
- 230000007062 hydrolysis Effects 0.000 claims description 8
- 229910052749 magnesium Inorganic materials 0.000 claims description 8
- 239000011777 magnesium Substances 0.000 claims description 8
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 8
- 239000003513 alkali Substances 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 239000002585 base Substances 0.000 claims description 7
- 150000005676 cyclic carbonates Chemical class 0.000 claims description 7
- 239000010452 phosphate Substances 0.000 claims description 7
- ZZXUZKXVROWEIF-UHFFFAOYSA-N 1,2-butylene carbonate Chemical compound CCC1COC(=O)O1 ZZXUZKXVROWEIF-UHFFFAOYSA-N 0.000 claims description 6
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims description 6
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 claims description 6
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 claims description 6
- 229940091173 hydantoin Drugs 0.000 claims description 6
- 229910052740 iodine Inorganic materials 0.000 claims description 6
- 239000003456 ion exchange resin Substances 0.000 claims description 6
- 229920003303 ion-exchange polymer Polymers 0.000 claims description 6
- 244000005700 microbiome Species 0.000 claims description 6
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 claims description 6
- 239000011592 zinc chloride Substances 0.000 claims description 6
- 235000005074 zinc chloride Nutrition 0.000 claims description 6
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims description 6
- 241000894006 Bacteria Species 0.000 claims description 5
- 229910021536 Zeolite Inorganic materials 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims description 5
- QJPWUUJVYOJNMH-UHFFFAOYSA-N homoserine lactone Chemical compound NC1CCOC1=O QJPWUUJVYOJNMH-UHFFFAOYSA-N 0.000 claims description 5
- 239000000543 intermediate Substances 0.000 claims description 5
- 229920000172 poly(styrenesulfonic acid) Polymers 0.000 claims description 5
- 229940005642 polystyrene sulfonic acid Drugs 0.000 claims description 5
- 238000007363 ring formation reaction Methods 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- 239000010457 zeolite Substances 0.000 claims description 5
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 4
- 229910015845 BBr3 Inorganic materials 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 4
- 229910021578 Iron(III) chloride Inorganic materials 0.000 claims description 4
- 229910006121 SOBr2 Inorganic materials 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 claims description 4
- 239000011630 iodine Substances 0.000 claims description 4
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 claims description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 4
- 239000000725 suspension Substances 0.000 claims description 4
- HFRXJVQOXRXOPP-UHFFFAOYSA-N thionyl bromide Chemical compound BrS(Br)=O HFRXJVQOXRXOPP-UHFFFAOYSA-N 0.000 claims description 4
- AVRSCQPPNAUXAL-UHFFFAOYSA-N 1,1,2,2,4,5,5,7,8,8-decafluoro-3,6-dioxo-4-(trifluoromethyl)oct-7-ene-1-sulfonic acid Chemical compound OS(=O)(=O)C(F)(F)C(F)(F)C(=O)C(F)(C(F)(F)F)C(F)(F)C(=O)C(F)=C(F)F AVRSCQPPNAUXAL-UHFFFAOYSA-N 0.000 claims description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims description 3
- 239000012973 diazabicyclooctane Substances 0.000 claims description 3
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- KYVBNYUBXIEUFW-UHFFFAOYSA-N 1,1,3,3-tetramethylguanidine Chemical compound CN(C)C(=N)N(C)C KYVBNYUBXIEUFW-UHFFFAOYSA-N 0.000 claims description 2
- 125000005999 2-bromoethyl group Chemical group 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 241000186216 Corynebacterium Species 0.000 claims description 2
- 241000588722 Escherichia Species 0.000 claims description 2
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 claims description 2
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 2
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 239000007900 aqueous suspension Substances 0.000 claims description 2
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 claims description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 2
- 238000012258 culturing Methods 0.000 claims description 2
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 2
- 239000004312 hexamethylene tetramine Substances 0.000 claims description 2
- 235000010299 hexamethylene tetramine Nutrition 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 2
- 150000004679 hydroxides Chemical class 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 235000015097 nutrients Nutrition 0.000 claims description 2
- 150000003222 pyridines Chemical class 0.000 claims description 2
- 239000012265 solid product Substances 0.000 claims description 2
- 150000003512 tertiary amines Chemical class 0.000 claims description 2
- 150000005622 tetraalkylammonium hydroxides Chemical class 0.000 claims description 2
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 claims description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims 5
- ZBZJXHCVGLJWFG-UHFFFAOYSA-N trichloromethyl(.) Chemical compound Cl[C](Cl)Cl ZBZJXHCVGLJWFG-UHFFFAOYSA-N 0.000 claims 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- VBOAPLSWMJQASY-UHFFFAOYSA-N carbonic acid 1,3-dioxepan-2-one Chemical compound C(O)(O)=O.C1(OCCCCO1)=O VBOAPLSWMJQASY-UHFFFAOYSA-N 0.000 claims 2
- 229920000642 polymer Polymers 0.000 claims 2
- 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
- 239000004793 Polystyrene Substances 0.000 claims 1
- 150000002500 ions Chemical class 0.000 claims 1
- 229920002223 polystyrene Polymers 0.000 claims 1
- 150000003254 radicals Chemical class 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
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 claims 1
- 239000000126 substance Substances 0.000 abstract description 16
- 235000006109 methionine Nutrition 0.000 description 37
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 29
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 16
- 230000008569 process Effects 0.000 description 12
- 238000004128 high performance liquid chromatography Methods 0.000 description 9
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 8
- 230000010933 acylation Effects 0.000 description 8
- 238000005917 acylation reaction Methods 0.000 description 8
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- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
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- WPLOVIFNBMNBPD-ATHMIXSHSA-N subtilin Chemical compound CC1SCC(NC2=O)C(=O)NC(CC(N)=O)C(=O)NC(C(=O)NC(CCCCN)C(=O)NC(C(C)CC)C(=O)NC(=C)C(=O)NC(CCCCN)C(O)=O)CSC(C)C2NC(=O)C(CC(C)C)NC(=O)C1NC(=O)C(CCC(N)=O)NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C1NC(=O)C(=C/C)/NC(=O)C(CCC(N)=O)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)CNC(=O)C(NC(=O)C(NC(=O)C2NC(=O)CNC(=O)C3CCCN3C(=O)C(NC(=O)C3NC(=O)C(CC(C)C)NC(=O)C(=C)NC(=O)C(CCC(O)=O)NC(=O)C(NC(=O)C(CCCCN)NC(=O)C(N)CC=4C5=CC=CC=C5NC=4)CSC3)C(C)SC2)C(C)C)C(C)SC1)CC1=CC=CC=C1 WPLOVIFNBMNBPD-ATHMIXSHSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/24—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of esters of sulfuric acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D307/30—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/32—Oxygen atoms
- C07D307/33—Oxygen atoms in position 2, the oxygen atom being in its keto or unsubstituted enol form
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
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 (1)
| Publication Number | Publication Date |
|---|---|
| BRPI0707299A2 true BRPI0707299A2 (pt) | 2011-05-03 |
Family
ID=37771916
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BRPI0707299-6A BRPI0707299A2 (pt) | 2006-01-28 | 2007-01-04 | método para produzir metionina a partir de homosserina |
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) |
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| 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 |
| US8865920B2 (en) * | 2010-03-09 | 2014-10-21 | Novus International, Inc. | N-acylation of amines |
| JP2012184213A (ja) * | 2010-04-06 | 2012-09-27 | Sumitomo Chemical Co Ltd | 含硫アミノ酸の製造方法 |
| JP2011231103A (ja) * | 2010-04-06 | 2011-11-17 | 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 |
| WO2015141886A1 (ko) * | 2014-03-20 | 2015-09-24 | 씨제이제일제당(주) | 미생물 유래의 o-아실호모세린으로부터 바이오 유래 호모세린락톤 염산염 및 바이오 유래 유기산을 제조하는 방법 |
| 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 |
| 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 |
| WO2017089077A1 (en) * | 2015-11-27 | 2017-06-01 | Evonik Degussa Gmbh | Method for producing l-methionine |
| CN108473967B (zh) | 2015-12-17 | 2022-03-29 | 赢创运营有限公司 | 基因修饰的产乙酸细胞 |
| JP2019523271A (ja) * | 2016-07-27 | 2019-08-22 | エボニック デグサ ゲーエムベーハーＥｖｏｎｉｋ Ｄｅｇｕｓｓａ ＧｍｂＨ | Ｎ−アセチルホモセリン |
| 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 |
| AR132026A1 (es) * | 2023-03-01 | 2025-05-21 | Hunan Lier Biotech Co Ltd | Un proceso de preparación de l-metionina directamente a partir de l-homoserina |
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| 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 | ||
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| 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) |
| ATE330022T1 (de) | 2000-12-22 | 2006-07-15 | Ajinomoto Kk | Verfahren zur herstellung einer zielsubstanz durch fermentation |
| EP1511724B1 (en) * | 2002-05-24 | 2014-04-30 | Bayer CropScience AG | Process for the preparation of thioalkylamine derivatives |
| 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
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2007
- 2007-01-04 BR BRPI0707299-6A patent/BRPI0707299A2/pt not_active IP Right Cessation
- 2007-01-04 EP EP07703642.4A patent/EP1976827B1/de not_active Not-in-force
- 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 RU RU2008134625/04A patent/RU2472778C2/ru not_active IP Right Cessation
- 2007-01-04 WO PCT/EP2007/050082 patent/WO2007085514A2/de not_active Ceased
- 2007-01-04 JP JP2008551744A patent/JP5383203B2/ja not_active Expired - Fee Related
- 2007-01-25 US US11/657,534 patent/US7368600B2/en not_active Expired - Fee Related
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2008
- 2008-02-13 US US12/068,951 patent/US7884240B2/en not_active Expired - Fee Related
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| Publication number | Publication date |
|---|---|
| US7368600B2 (en) | 2008-05-06 |
| CA2640523A1 (en) | 2007-08-02 |
| CN101374806A (zh) | 2009-02-25 |
| RU2008134625A (ru) | 2010-03-10 |
| EP1976827A2 (de) | 2008-10-08 |
| JP5383203B2 (ja) | 2014-01-08 |
| US20080146840A1 (en) | 2008-06-19 |
| RU2472778C2 (ru) | 2013-01-20 |
| DE102006004063A1 (de) | 2007-08-02 |
| JP2009524615A (ja) | 2009-07-02 |
| US20070190622A1 (en) | 2007-08-16 |
| EP1976827B1 (de) | 2017-12-13 |
| CN101374806B (zh) | 2013-03-27 |
| US7884240B2 (en) | 2011-02-08 |
| WO2007085514A2 (de) | 2007-08-02 |
| WO2007085514A3 (de) | 2008-07-03 |
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