DE814296C - Verfahren zur Trennung und Gewinnung der optischen Antipoden von racemischen Aminosaeuren - Google Patents
Verfahren zur Trennung und Gewinnung der optischen Antipoden von racemischen AminosaeurenInfo
- Publication number
- DE814296C DE814296C DEJ287D DEJ0000287D DE814296C DE 814296 C DE814296 C DE 814296C DE J287 D DEJ287 D DE J287D DE J0000287 D DEJ0000287 D DE J0000287D DE 814296 C DE814296 C DE 814296C
- Authority
- DE
- Germany
- Prior art keywords
- solution
- acid
- amidase
- amino acid
- enzyme
- 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.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims description 29
- 150000001413 amino acids Chemical class 0.000 title claims description 27
- 230000003287 optical effect Effects 0.000 title claims description 24
- 238000000926 separation method Methods 0.000 title claims description 8
- 238000011084 recovery Methods 0.000 title claims description 3
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims description 36
- 108090000790 Enzymes Proteins 0.000 claims description 34
- 102000004190 Enzymes Human genes 0.000 claims description 34
- 229940024606 amino acid Drugs 0.000 claims description 27
- 235000001014 amino acid Nutrition 0.000 claims description 27
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 24
- 229910000019 calcium carbonate Inorganic materials 0.000 claims description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
- 238000003776 cleavage reaction Methods 0.000 claims description 14
- 230000007017 scission Effects 0.000 claims description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 12
- 108700023418 Amidases Proteins 0.000 claims description 12
- 102000005922 amidase Human genes 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 10
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 10
- 235000019441 ethanol Nutrition 0.000 claims description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 8
- 238000009835 boiling Methods 0.000 claims description 6
- QIVBCDIJIAJPQS-UHFFFAOYSA-N tryptophan Chemical compound C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 claims description 6
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 5
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 5
- 230000000694 effects Effects 0.000 claims description 5
- 229930195729 fatty acid Natural products 0.000 claims description 5
- 239000000194 fatty acid Substances 0.000 claims description 5
- 150000004665 fatty acids Chemical class 0.000 claims description 5
- 238000001914 filtration Methods 0.000 claims description 5
- 235000019253 formic acid Nutrition 0.000 claims description 5
- 229910021529 ammonia Inorganic materials 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 4
- KDXKERNSBIXSRK-UHFFFAOYSA-N lysine Chemical compound NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims description 4
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Chemical compound OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 claims description 4
- 125000004442 acylamino group Chemical group 0.000 claims description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 3
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 2
- VMZCDNSFRSVYKQ-UHFFFAOYSA-N 2-phenylacetyl chloride Chemical compound ClC(=O)CC1=CC=CC=C1 VMZCDNSFRSVYKQ-UHFFFAOYSA-N 0.000 claims description 2
- 150000008064 anhydrides Chemical class 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 230000002349 favourable effect Effects 0.000 claims 3
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 claims 1
- 239000012346 acetyl chloride Substances 0.000 claims 1
- 230000010933 acylation Effects 0.000 claims 1
- 238000005917 acylation reaction Methods 0.000 claims 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 claims 1
- 230000003139 buffering effect Effects 0.000 claims 1
- 230000003472 neutralizing effect Effects 0.000 claims 1
- 230000001681 protective effect Effects 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 57
- 239000000243 solution Substances 0.000 description 46
- 229940088598 enzyme Drugs 0.000 description 33
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 238000001704 evaporation Methods 0.000 description 12
- 230000008020 evaporation Effects 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical compound C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 description 9
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 8
- 239000000284 extract Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 229960004799 tryptophan Drugs 0.000 description 7
- DZTHIGRZJZPRDV-LBPRGKRZSA-N N-acetyl-L-tryptophan Chemical compound C1=CC=C2C(C[C@H](NC(=O)C)C(O)=O)=CNC2=C1 DZTHIGRZJZPRDV-LBPRGKRZSA-N 0.000 description 6
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 6
- 238000000605 extraction Methods 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- 108010021511 Aspergillus oryzae carboxyl proteinase Proteins 0.000 description 5
- AGPKZVBTJJNPAG-WHFBIAKZSA-N L-isoleucine Chemical compound CC[C@H](C)[C@H](N)C(O)=O AGPKZVBTJJNPAG-WHFBIAKZSA-N 0.000 description 5
- QIAFMBKCNZACKA-UHFFFAOYSA-N N-benzoylglycine Chemical compound OC(=O)CNC(=O)C1=CC=CC=C1 QIAFMBKCNZACKA-UHFFFAOYSA-N 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 229960000310 isoleucine Drugs 0.000 description 5
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- QNAYBMKLOCPYGJ-UHFFFAOYSA-N D-alpha-Ala Natural products CC([NH3+])C([O-])=O QNAYBMKLOCPYGJ-UHFFFAOYSA-N 0.000 description 4
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 description 4
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 description 4
- 229910052791 calcium Inorganic materials 0.000 description 4
- 239000011575 calcium Substances 0.000 description 4
- AGPKZVBTJJNPAG-UHFFFAOYSA-N isoleucine Natural products CCC(C)C(N)C(O)=O AGPKZVBTJJNPAG-UHFFFAOYSA-N 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000005711 Benzoic acid Substances 0.000 description 3
- BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 description 3
- QNAYBMKLOCPYGJ-UWTATZPHSA-N L-Alanine Natural products C[C@@H](N)C(O)=O QNAYBMKLOCPYGJ-UWTATZPHSA-N 0.000 description 3
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-Lysine Natural products NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 3
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 3
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 3
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 description 3
- 239000004472 Lysine Substances 0.000 description 3
- 229960003767 alanine Drugs 0.000 description 3
- 229960005261 aspartic acid Drugs 0.000 description 3
- 235000010233 benzoic acid Nutrition 0.000 description 3
- -1 benzoyl aspartic acid Chemical compound 0.000 description 3
- 229910001424 calcium ion Inorganic materials 0.000 description 3
- 159000000007 calcium salts Chemical class 0.000 description 3
- 238000004140 cleaning Methods 0.000 description 3
- 229940079919 digestives enzyme preparation Drugs 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- FFEARJCKVFRZRR-UHFFFAOYSA-N methionine Chemical compound CSCCC(N)C(O)=O FFEARJCKVFRZRR-UHFFFAOYSA-N 0.000 description 3
- 229960004452 methionine Drugs 0.000 description 3
- 235000006408 oxalic acid Nutrition 0.000 description 3
- 229960005190 phenylalanine Drugs 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 229960004441 tyrosine Drugs 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000003855 acyl compounds Chemical class 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 108010003977 aminoacylase I Proteins 0.000 description 2
- 235000003704 aspartic acid Nutrition 0.000 description 2
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 2
- 208000015181 infectious disease Diseases 0.000 description 2
- 235000018977 lysine Nutrition 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 229930182817 methionine Natural products 0.000 description 2
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Chemical compound OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 2
- YAYNEUUHHLGGAH-UHFFFAOYSA-N 1-chlorododecane Chemical compound CCCCCCCCCCCCCl YAYNEUUHHLGGAH-UHFFFAOYSA-N 0.000 description 1
- CLWAXFZCVYJLLM-UHFFFAOYSA-N 1-chlorohexadecane Chemical compound CCCCCCCCCCCCCCCCCl CLWAXFZCVYJLLM-UHFFFAOYSA-N 0.000 description 1
- PPFRJEXUPZWQPI-UHFFFAOYSA-N 2-benzamido-4-methylsulfanylbutanoic acid Chemical compound CSCCC(C(O)=O)NC(=O)C1=CC=CC=C1 PPFRJEXUPZWQPI-UHFFFAOYSA-N 0.000 description 1
- 108090000531 Amidohydrolases Proteins 0.000 description 1
- 102000004092 Amidohydrolases Human genes 0.000 description 1
- 240000006439 Aspergillus oryzae Species 0.000 description 1
- 235000002247 Aspergillus oryzae Nutrition 0.000 description 1
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 1
- CKLJMWTZIZZHCS-UHFFFAOYSA-N D-OH-Asp Natural products OC(=O)C(N)CC(O)=O CKLJMWTZIZZHCS-UHFFFAOYSA-N 0.000 description 1
- KDXKERNSBIXSRK-RXMQYKEDSA-N D-lysine Chemical compound NCCCC[C@@H](N)C(O)=O KDXKERNSBIXSRK-RXMQYKEDSA-N 0.000 description 1
- VEXZGXHMUGYJMC-DYCDLGHISA-N Deuterium chloride Chemical compound [2H]Cl VEXZGXHMUGYJMC-DYCDLGHISA-N 0.000 description 1
- CKLJMWTZIZZHCS-UWTATZPHSA-N L-Aspartic acid Natural products OC(=O)[C@H](N)CC(O)=O CKLJMWTZIZZHCS-UWTATZPHSA-N 0.000 description 1
- 235000019766 L-Lysine Nutrition 0.000 description 1
- 150000008575 L-amino acids Chemical class 0.000 description 1
- 229930182844 L-isoleucine Natural products 0.000 description 1
- BVHLGVCQOALMSV-JEDNCBNOSA-N L-lysine hydrochloride Chemical compound Cl.NCCCC[C@H](N)C(O)=O BVHLGVCQOALMSV-JEDNCBNOSA-N 0.000 description 1
- 229930195722 L-methionine Natural products 0.000 description 1
- XUYPXLNMDZIRQH-LURJTMIESA-N N-acetyl-L-methionine Chemical compound CSCC[C@@H](C(O)=O)NC(C)=O XUYPXLNMDZIRQH-LURJTMIESA-N 0.000 description 1
- UAQVHNZEONHPQG-UHFFFAOYSA-N N-benzoylalanine Chemical compound OC(=O)C(C)NC(=O)C1=CC=CC=C1 UAQVHNZEONHPQG-UHFFFAOYSA-N 0.000 description 1
- LIIPHJDKZNTNII-HNNXBMFYSA-N N-phenylacetylphenylalanine Chemical compound C([C@@H](C(=O)O)NC(=O)CC=1C=CC=CC=1)C1=CC=CC=C1 LIIPHJDKZNTNII-HNNXBMFYSA-N 0.000 description 1
- 108010019160 Pancreatin Proteins 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 230000021736 acetylation Effects 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- QXDMQSPYEZFLGF-UHFFFAOYSA-L calcium oxalate Chemical compound [Ca+2].[O-]C(=O)C([O-])=O QXDMQSPYEZFLGF-UHFFFAOYSA-L 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000002026 chloroform extract Substances 0.000 description 1
- 230000001112 coagulating effect Effects 0.000 description 1
- 238000005345 coagulation Methods 0.000 description 1
- 230000015271 coagulation Effects 0.000 description 1
- IQFVPQOLBLOTPF-HKXUKFGYSA-L congo red Chemical compound [Na+].[Na+].C1=CC=CC2=C(N)C(/N=N/C3=CC=C(C=C3)C3=CC=C(C=C3)/N=N/C3=C(C4=CC=CC=C4C(=C3)S([O-])(=O)=O)N)=CC(S([O-])(=O)=O)=C21 IQFVPQOLBLOTPF-HKXUKFGYSA-L 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000006911 enzymatic reaction Methods 0.000 description 1
- 239000000469 ethanolic extract Substances 0.000 description 1
- 239000002024 ethyl acetate extract Substances 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 229960002449 glycine Drugs 0.000 description 1
- 235000013905 glycine and its sodium salt Nutrition 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 229940055695 pancreatin Drugs 0.000 description 1
- 229960003424 phenylacetic acid Drugs 0.000 description 1
- 239000003279 phenylacetic acid Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 235000013311 vegetables Nutrition 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
-
- 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
-
- 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
- C12P13/06—Alanine; Leucine; Isoleucine; Serine; Homoserine
-
- 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
- C12P13/08—Lysine; Diaminopimelic acid; Threonine; Valine
-
- 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
- C12P13/20—Aspartic acid; Asparagine
-
- 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
- C12P13/22—Tryptophan; Tyrosine; Phenylalanine; 3,4-Dihydroxyphenylalanine
-
- 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
- C12P41/00—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture
- C12P41/006—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture by reactions involving C-N bonds, e.g. nitriles, amides, hydantoins, carbamates, lactames, transamination reactions, or keto group formation from racemic mixtures
- C12P41/007—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture by reactions involving C-N bonds, e.g. nitriles, amides, hydantoins, carbamates, lactames, transamination reactions, or keto group formation from racemic mixtures by reactions involving acyl derivatives of racemic amines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (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)
- Analytical Chemistry (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB32493/49A GB675603A (en) | 1949-12-19 | 1949-12-19 | Improvements in or relating to the separation of racemic amino acids |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE814296C true DE814296C (de) | 1951-09-20 |
Family
ID=10339440
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEJ287D Expired DE814296C (de) | 1949-12-19 | 1949-12-20 | Verfahren zur Trennung und Gewinnung der optischen Antipoden von racemischen Aminosaeuren |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US2511867A (en, 2012) |
| BE (1) | BE494517A (en, 2012) |
| CH (1) | CH284412A (en, 2012) |
| DE (1) | DE814296C (en, 2012) |
| FR (1) | FR1018782A (en, 2012) |
| GB (1) | GB675603A (en, 2012) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1148140A1 (en) * | 2000-04-19 | 2001-10-24 | Basilea Pharmaceutica AG | Process for the preparation of D-asparagine derivatives |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2616828A (en) * | 1951-04-30 | 1952-11-04 | Levintow Leon | Method of enzymatic resolution of amino acids |
| US2799684A (en) * | 1954-06-18 | 1957-07-16 | Food Chemical And Res Lab Inc | Crystalline compounds of tryptophane and methods of manufacturing them |
| US2844513A (en) * | 1955-07-20 | 1958-07-22 | Ciba Pharm Prod Inc | Process for splitting racemates |
| US2833694A (en) * | 1955-08-25 | 1958-05-06 | Ciba Pharm Prod Inc | Process for splitting racemates |
| CH341493A (de) * | 1955-08-25 | 1959-10-15 | Ciba Geigy | Verfahren zur Racematspaltung |
| AT313224B (de) * | 1970-01-19 | 1974-01-15 | Astra Laekemedel Ab | Verfahren zur herstellung von l(-)-3-(3,4-dihydroxyphenyl)-alanin undl (-)-3-(3-hydroxyphenyl)-alanin und den entsprechenden veraetherten derivaten |
| US3963573A (en) * | 1975-03-03 | 1976-06-15 | The Procter & Gamble Company | Process for producing N-acyl-L-methionine |
| CH605474A5 (en, 2012) * | 1976-10-12 | 1978-09-29 | Hoffmann La Roche | |
| US4205183A (en) * | 1978-12-08 | 1980-05-27 | Beckman Instruments, Inc. | Facile method for isolating resolved amino acids |
| US4366250A (en) * | 1980-09-24 | 1982-12-28 | Anvar | Preparation process of optically active α-aminated acids by biological hydrolysis of nitriles |
| DE3318933C1 (de) * | 1983-05-25 | 1984-06-07 | Degussa Ag, 6000 Frankfurt | Verfahren zur Trennung von L-Leucin und L-Isoleucin |
| DE3318932C1 (de) * | 1983-05-25 | 1984-06-07 | Degussa Ag, 6000 Frankfurt | Verfahren zur Gewinnung von reinem L-Leucin |
| SU1719433A1 (ru) * | 1988-04-26 | 1992-03-15 | Научно-Исследовательский Технологический Институт Аминокислот | Способ получени L-аланина |
| RU2096460C1 (ru) * | 1991-03-06 | 1997-11-20 | Лонца Аг | Способ получения s-(+)-2,2-диметилциклопропанкарбоксамида, штаммы бактерий comamonas acidovorans, pseudomonas sp., bacterium sp., предназначенные для получения s-(+)-2,2-диметилциклопропанкарбоксамида (варианты) |
| DK0524604T3 (da) * | 1991-07-26 | 1999-06-23 | Lonza Ag | Genteknologisk fremgangsmåde til fremstilling af S-(+)-2,2-dimethylcyclopropancarboxamid ved hjælp af mikroorganismer |
-
1948
- 1948-07-17 US US3937348 patent/US2511867A/en not_active Expired - Lifetime
-
1949
- 1949-12-10 CH CH284412D patent/CH284412A/de unknown
- 1949-12-19 GB GB32493/49A patent/GB675603A/en not_active Expired
- 1949-12-20 DE DEJ287D patent/DE814296C/de not_active Expired
-
1950
- 1950-03-07 FR FR1018782D patent/FR1018782A/fr not_active Expired
- 1950-03-14 BE BE494517D patent/BE494517A/xx unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1148140A1 (en) * | 2000-04-19 | 2001-10-24 | Basilea Pharmaceutica AG | Process for the preparation of D-asparagine derivatives |
Also Published As
| Publication number | Publication date |
|---|---|
| CH284412A (de) | 1952-07-31 |
| FR1018782A (fr) | 1953-01-13 |
| US2511867A (en) | 1950-06-20 |
| BE494517A (en, 2012) | 1950-07-01 |
| GB675603A (en) | 1952-07-16 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE814296C (de) | Verfahren zur Trennung und Gewinnung der optischen Antipoden von racemischen Aminosaeuren | |
| DE1171931B (de) | Verfahren zur Herstellung antihypertonisch wirkender Phenylalaninderivate | |
| DE2526594A1 (de) | Verfahren zur enzymatischen spaltung von dl-phenylglycinamid in dessen optisch aktive antipoden | |
| DE2824116C2 (en, 2012) | ||
| DE2518160C2 (en, 2012) | ||
| EP0090087B1 (de) | Verfahren zur Gewinnung von S-(Carboxymethyl)-(R)-cystein und S-(Carboxymethyl)-(S)-cystein | |
| DE3317666C2 (en, 2012) | ||
| DE69016017T2 (de) | Verfahren zur reinigung von hemin, neues heminderivat und verfahren zur herstellung. | |
| CH497384A (de) | Verfahren zur Herstellung eines Dekapeptides | |
| DE1695894C3 (de) | Verfahren zur Herstellung von D- und L-Prolin | |
| DE1245982B (de) | Verfahren zur Herstellung von L(-)-B-(3,4-Dihydroxy-phenyl)-a-methyl-alanin | |
| DE2100445A1 (de) | Verfahren zur Herstellung von L Dopa und L m Tyrosin | |
| DE1902582A1 (de) | Verfahren zur Herstellung von Phenylalaninderivaten | |
| DE687555C (de) | Verfahren zur Herstellung von Aminoalkoholen | |
| AT261592B (de) | Verfahren zur Herstellung L-(-)-α-Methyl-β-(3,4-dihydroxyphenyl)-alanin | |
| DE1039061B (de) | Verfahren zur Herstellung N-substituierter 3-Aminoisocamphanverbindungen, deren Salzen, quaternaeren Ammoniumverbindungen und optisch aktiven Isomeren | |
| DE1493484C3 (de) | Verfahren zur Herstellung von L-(-)-aIpha-Methyl-beta-(3,4-dihydroxyphenyl)-alanin | |
| DE386743C (de) | Verfahren zur Darstellung von N-Alkylaminofettsaeuren und deren N-Acidylderivaten | |
| DE2348616A1 (de) | Verfahren zur trennung von dl-tryptophan-benzolsulfonat oder dl-tryptophan-pphenolsulfonat in ihre optischen antipoden und gegebenenfalls ueberfuehrung derselben in optisch aktives tryptophan | |
| AT333246B (de) | Verfahren zur herstellung von neuem 3-fluor-d-alanin, von neuen deutero-analogen desselben, von amid- und esterderivaten dieser verbindungen oder von n-derivaten dieser verbindungen | |
| DE2408747A1 (de) | Zubereitungen, die vollsynthetisch hergestelltes d-penicillamin enthalten | |
| DE2302937B2 (de) | Verfahren zur herstellung der optischen antipoden des alpha-methyl- beta-(3,4-dihydroxyphenyl)-alanins | |
| JPS63112571A (ja) | Ｌ−チアゾリジン−４−カルボン酸のラセミ化法 | |
| DE1065424B (de) | Verfahren zur Herstellung von Pepfiden | |
| DE1296641B (de) | Verfahren zur Herstellung von L-Aminosaeuren |