NL8201979A - Werkwijze voor de bereiding van l-alfa-methylfenylalaninen. - Google Patents
Werkwijze voor de bereiding van l-alfa-methylfenylalaninen. Download PDFInfo
- Publication number
- NL8201979A NL8201979A NL8201979A NL8201979A NL8201979A NL 8201979 A NL8201979 A NL 8201979A NL 8201979 A NL8201979 A NL 8201979A NL 8201979 A NL8201979 A NL 8201979A NL 8201979 A NL8201979 A NL 8201979A
- Authority
- NL
- Netherlands
- Prior art keywords
- methylphenylalanine
- genus
- amides
- ifo
- amide
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 22
- 238000002360 preparation method Methods 0.000 title claims description 5
- 239000000203 mixture Substances 0.000 claims description 21
- -1 DL-α-methylphenyl-alanine amides Chemical class 0.000 claims description 19
- 244000005700 microbiome Species 0.000 claims description 19
- 238000006460 hydrolysis reaction Methods 0.000 claims description 17
- 230000007062 hydrolysis Effects 0.000 claims description 16
- 102000004190 Enzymes Human genes 0.000 claims description 15
- 108090000790 Enzymes Proteins 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 241000222120 Candida <Saccharomycetales> Species 0.000 claims description 7
- 241000223218 Fusarium Species 0.000 claims description 5
- 241000235648 Pichia Species 0.000 claims description 5
- 241000589516 Pseudomonas Species 0.000 claims description 5
- 241000187654 Nocardia Species 0.000 claims description 4
- 230000035484 reaction time Effects 0.000 claims description 4
- 241000186063 Arthrobacter Species 0.000 claims description 3
- 241000193830 Bacillus <bacterium> Species 0.000 claims description 3
- 241000186359 Mycobacterium Species 0.000 claims description 3
- 241000235527 Rhizopus Species 0.000 claims description 3
- 241000187747 Streptomyces Species 0.000 claims description 3
- 241000223259 Trichoderma Species 0.000 claims description 3
- HYOWVAAEQCNGLE-UHFFFAOYSA-N alpha-Methylphenylalanine Chemical compound OC(=O)C(N)(C)CC1=CC=CC=C1 HYOWVAAEQCNGLE-UHFFFAOYSA-N 0.000 claims description 3
- 150000001408 amides Chemical class 0.000 claims description 3
- 241000588914 Enterobacter Species 0.000 claims description 2
- 241000223252 Rhodotorula Species 0.000 claims description 2
- 241000221566 Ustilago Species 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 239000000758 substrate Substances 0.000 description 17
- 229940088598 enzyme Drugs 0.000 description 14
- 239000000047 product Substances 0.000 description 14
- 239000011541 reaction mixture Substances 0.000 description 14
- 230000003287 optical effect Effects 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000007788 liquid Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 241000186367 Mycobacterium avium Species 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 239000012153 distilled water Substances 0.000 description 5
- 239000008055 phosphate buffer solution Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 241000588915 Klebsiella aerogenes Species 0.000 description 4
- 235000004279 alanine Nutrition 0.000 description 4
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 4
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 4
- 235000011130 ammonium sulphate Nutrition 0.000 description 4
- 238000005119 centrifugation Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- HQMLIDZJXVVKCW-REOHCLBHSA-N L-alaninamide Chemical compound C[C@H](N)C(N)=O HQMLIDZJXVVKCW-REOHCLBHSA-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
- HYOWVAAEQCNGLE-JTQLQIEISA-N alpha-methyl-L-phenylalanine Chemical class OC(=O)[C@](N)(C)CC1=CC=CC=C1 HYOWVAAEQCNGLE-JTQLQIEISA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 229940079919 digestives enzyme preparation Drugs 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 241000235389 Absidia Species 0.000 description 2
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 2
- 229920001817 Agar Polymers 0.000 description 2
- 241000588986 Alcaligenes Species 0.000 description 2
- 244000063299 Bacillus subtilis Species 0.000 description 2
- 235000014469 Bacillus subtilis Nutrition 0.000 description 2
- 241000235646 Cyberlindnera jadinii Species 0.000 description 2
- 244000286779 Hansenula anomala Species 0.000 description 2
- 235000014683 Hansenula anomala Nutrition 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 241000187480 Mycobacterium smegmatis Species 0.000 description 2
- 241000193596 Nadsonia Species 0.000 description 2
- 241000203720 Pimelobacter simplex Species 0.000 description 2
- 241000589540 Pseudomonas fluorescens Species 0.000 description 2
- 241000235528 Rhizopus microsporus var. chinensis Species 0.000 description 2
- 241000192023 Sarcina Species 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 241000187392 Streptomyces griseus Species 0.000 description 2
- 241000223261 Trichoderma viride Species 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000008272 agar Substances 0.000 description 2
- 125000005219 aminonitrile group Chemical group 0.000 description 2
- 238000002306 biochemical method Methods 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 238000001640 fractional crystallisation Methods 0.000 description 2
- 238000011534 incubation Methods 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- 230000000813 microbial effect Effects 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- MWZIRLKBMIZSIZ-JTQLQIEISA-N (2s)-2-(dihydroxyamino)-2-methyl-3-phenylpropanoic acid Chemical class ON(O)[C@@](C(O)=O)(C)CC1=CC=CC=C1 MWZIRLKBMIZSIZ-JTQLQIEISA-N 0.000 description 1
- PYRTVXRJEYPGJX-VIFPVBQESA-N (2s)-2-(methylamino)-3-phenylpropanamide Chemical compound CN[C@H](C(N)=O)CC1=CC=CC=C1 PYRTVXRJEYPGJX-VIFPVBQESA-N 0.000 description 1
- YKFCISHFRZHKHY-NGQGLHOPSA-N (2s)-2-amino-3-(3,4-dihydroxyphenyl)-2-methylpropanoic acid;trihydrate Chemical compound O.O.O.OC(=O)[C@](N)(C)CC1=CC=C(O)C(O)=C1.OC(=O)[C@](N)(C)CC1=CC=C(O)C(O)=C1 YKFCISHFRZHKHY-NGQGLHOPSA-N 0.000 description 1
- GYLLCZASLVXHHI-GRHHLOCNSA-N (2s)-2-amino-3-phenylpropanamide;(2s)-2-amino-3-phenylpropanoic acid Chemical compound NC(=O)[C@@H](N)CC1=CC=CC=C1.OC(=O)[C@@H](N)CC1=CC=CC=C1 GYLLCZASLVXHHI-GRHHLOCNSA-N 0.000 description 1
- MTPJEFOSTIKRSS-UHFFFAOYSA-N 3-(dimethylamino)propanenitrile Chemical compound CN(C)CCC#N MTPJEFOSTIKRSS-UHFFFAOYSA-N 0.000 description 1
- UHPMCKVQTMMPCG-UHFFFAOYSA-N 5,8-dihydroxy-2-methoxy-6-methyl-7-(2-oxopropyl)naphthalene-1,4-dione Chemical compound CC1=C(CC(C)=O)C(O)=C2C(=O)C(OC)=CC(=O)C2=C1O UHPMCKVQTMMPCG-UHFFFAOYSA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- 241000908198 Actinomucor Species 0.000 description 1
- 241000589158 Agrobacterium Species 0.000 description 1
- 241000589155 Agrobacterium tumefaciens Species 0.000 description 1
- 108700023418 Amidases Proteins 0.000 description 1
- 241000228212 Aspergillus Species 0.000 description 1
- 241000228245 Aspergillus niger Species 0.000 description 1
- 241000223678 Aureobasidium pullulans Species 0.000 description 1
- 241000722885 Brettanomyces Species 0.000 description 1
- 241001522017 Brettanomyces anomalus Species 0.000 description 1
- 241000186146 Brevibacterium Species 0.000 description 1
- 229920000298 Cellophane Polymers 0.000 description 1
- 241001149472 Clonostachys rosea Species 0.000 description 1
- 241000193403 Clostridium Species 0.000 description 1
- 241000193401 Clostridium acetobutylicum Species 0.000 description 1
- 102000008186 Collagen Human genes 0.000 description 1
- 108010035532 Collagen Proteins 0.000 description 1
- 241000186145 Corynebacterium ammoniagenes Species 0.000 description 1
- 241001337994 Cryptococcus <scale insect> Species 0.000 description 1
- 241000235555 Cunninghamella Species 0.000 description 1
- 241000235556 Cunninghamella elegans Species 0.000 description 1
- 241001149409 Cystobasidium minutum Species 0.000 description 1
- 241000589565 Flavobacterium Species 0.000 description 1
- 241000221778 Fusarium fujikuroi Species 0.000 description 1
- 241000221779 Fusarium sambucinum Species 0.000 description 1
- 241000159512 Geotrichum Species 0.000 description 1
- 244000168141 Geotrichum candidum Species 0.000 description 1
- 235000017388 Geotrichum candidum Nutrition 0.000 description 1
- 241000896533 Gliocladium Species 0.000 description 1
- 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 description 1
- 241000186660 Lactobacillus Species 0.000 description 1
- 244000199866 Lactobacillus casei Species 0.000 description 1
- 235000013958 Lactobacillus casei Nutrition 0.000 description 1
- 241001467579 Microbacterium arborescens Species 0.000 description 1
- 241000192041 Micrococcus Species 0.000 description 1
- 241000515012 Micrococcus flavus Species 0.000 description 1
- 125000003047 N-acetyl group Chemical group 0.000 description 1
- 241001443590 Naganishia albida Species 0.000 description 1
- 241000187678 Nocardia asteroides Species 0.000 description 1
- 241000228143 Penicillium Species 0.000 description 1
- 241000985530 Penicillium glabrum Species 0.000 description 1
- 239000005062 Polybutadiene Substances 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 241000235070 Saccharomyces Species 0.000 description 1
- 229920005654 Sephadex Polymers 0.000 description 1
- 239000012507 Sephadex™ Substances 0.000 description 1
- 241000228391 Sporidiobolus pararoseus Species 0.000 description 1
- 241000222068 Sporobolomyces <Sporidiobolaceae> Species 0.000 description 1
- 241000194017 Streptococcus Species 0.000 description 1
- 244000057717 Streptococcus lactis Species 0.000 description 1
- 235000014897 Streptococcus lactis Nutrition 0.000 description 1
- 244000301083 Ustilago maydis Species 0.000 description 1
- 235000015919 Ustilago maydis Nutrition 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 241000235033 Zygosaccharomyces rouxii Species 0.000 description 1
- SMEGJBVQLJJKKX-HOTMZDKISA-N [(2R,3S,4S,5R,6R)-5-acetyloxy-3,4,6-trihydroxyoxan-2-yl]methyl acetate Chemical compound CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)O)OC(=O)C)O)O SMEGJBVQLJJKKX-HOTMZDKISA-N 0.000 description 1
- 229940081735 acetylcellulose Drugs 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001295 alanines Chemical class 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 102000005922 amidase Human genes 0.000 description 1
- ICAIHGOJRDCMHE-UHFFFAOYSA-O ammonium cyanide Chemical compound [NH4+].N#[C-] ICAIHGOJRDCMHE-UHFFFAOYSA-O 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000003851 biochemical process Effects 0.000 description 1
- 239000000679 carrageenan Substances 0.000 description 1
- 229920001525 carrageenan Polymers 0.000 description 1
- 229940113118 carrageenan Drugs 0.000 description 1
- 235000010418 carrageenan Nutrition 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 229940083181 centrally acting adntiadrenergic agent methyldopa Drugs 0.000 description 1
- 229920001436 collagen Polymers 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 229940092559 enterobacter aerogenes Drugs 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000007863 gel particle Substances 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 229940039696 lactobacillus Drugs 0.000 description 1
- 229940017800 lactobacillus casei Drugs 0.000 description 1
- 235000009973 maize Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- QCCDLTOVEPVEJK-UHFFFAOYSA-N phenylacetone Chemical compound CC(=O)CC1=CC=CC=C1 QCCDLTOVEPVEJK-UHFFFAOYSA-N 0.000 description 1
- 238000000053 physical method Methods 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000011833 salt mixture Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 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
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
- C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
- C12N9/14—Hydrolases (3)
- C12N9/78—Hydrolases (3) acting on carbon to nitrogen bonds other than peptide bonds (3.5)
- C12N9/80—Hydrolases (3) acting on carbon to nitrogen bonds other than peptide bonds (3.5) acting on amide bonds in linear amides (3.5.1)
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Genetics & Genomics (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- General Engineering & Computer Science (AREA)
- Microbiology (AREA)
- Biotechnology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Biomedical Technology (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP56071397A JPS57186495A (en) | 1981-05-14 | 1981-05-14 | Preparation of l-alpha-methylphenylalanine |
| JP7139781 | 1981-05-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NL8201979A true NL8201979A (nl) | 1982-12-01 |
Family
ID=13459334
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL8201979A NL8201979A (nl) | 1981-05-14 | 1982-05-13 | Werkwijze voor de bereiding van l-alfa-methylfenylalaninen. |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US4443548A (en:Method) |
| JP (1) | JPS57186495A (en:Method) |
| DE (1) | DE3217908A1 (en:Method) |
| NL (1) | NL8201979A (en:Method) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4565782A (en) * | 1983-07-27 | 1986-01-21 | Imperial Chemical Industries Plc | Process for producing optically active aryloxypropionic acids and derivatives thereof useful as herbicides |
| JPS6098995A (ja) * | 1983-11-04 | 1985-06-01 | Microbial Chem Res Found | 光学活性３−（３，４−ジヒドロキシフエニル）セリン，およびその誘導体の製造法 |
| NL8400312A (nl) * | 1984-02-02 | 1985-09-02 | Stamicarbon | Optisch aktief gesubstitueerd boterzuuramide alsmede werkwijze voor de optische scheiding van gesubstitueerd boterzuuramide. |
| US5215897A (en) * | 1985-09-04 | 1993-06-01 | Nitto Chemical Industries Co., Ltd. | Process for producing L-amino acids |
| US5283193A (en) * | 1988-06-27 | 1994-02-01 | Asahi Kasei Kogyo K.K. | Process for producing optically active α-substituted organic acid and microorganism and enzyme used therefor |
| US5238828A (en) * | 1988-08-29 | 1993-08-24 | Idemitsu Kosan Company Limited | Method for the preparation of an optically active 2-substituted carboxylic acid |
| FR2655660B1 (fr) * | 1989-12-11 | 1992-03-20 | Rhone Poulenc Sante | Nouveaux polypeptides, sequences d'adn permettant leur expression, procede de preparation et leur utilisation. |
| NL9100038A (nl) * | 1991-01-11 | 1992-08-03 | Stamicarbon | Enzym-gekatalyseerde bereiding van optisch aktieve carbonzuren. |
| WO2003049752A2 (en) * | 2001-12-11 | 2003-06-19 | Institut Pasteur | Gram positive bacteria preparations for the treatment of diseases comprising an immune dysregulation |
| GB0413322D0 (en) * | 2004-06-15 | 2004-07-14 | Avecia Ltd | Process |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2807286A1 (de) * | 1978-02-21 | 1979-08-23 | Bayer Ag | Stereoselektive spaltung von phenylglycinderivaten und 4-hydroxyphenylglycinderivaten mit enzymharzen |
| US4366250A (en) * | 1980-09-24 | 1982-12-28 | Anvar | Preparation process of optically active α-aminated acids by biological hydrolysis of nitriles |
-
1981
- 1981-05-14 JP JP56071397A patent/JPS57186495A/ja active Pending
-
1982
- 1982-05-07 US US06/376,236 patent/US4443548A/en not_active Expired - Fee Related
- 1982-05-12 DE DE3217908A patent/DE3217908A1/de active Granted
- 1982-05-13 NL NL8201979A patent/NL8201979A/nl not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| DE3217908A1 (de) | 1982-12-23 |
| US4443548A (en) | 1984-04-17 |
| DE3217908C2 (en:Method) | 1989-02-09 |
| JPS57186495A (en) | 1982-11-16 |
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