DE3424440C2 - - Google Patents
Info
- Publication number
- DE3424440C2 DE3424440C2 DE3424440A DE3424440A DE3424440C2 DE 3424440 C2 DE3424440 C2 DE 3424440C2 DE 3424440 A DE3424440 A DE 3424440A DE 3424440 A DE3424440 A DE 3424440A DE 3424440 C2 DE3424440 C2 DE 3424440C2
- Authority
- DE
- Germany
- Prior art keywords
- mercapto
- cells
- acetyl
- reaction
- carboxylic acid
- 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 - Lifetime
Links
- 244000005700 microbiome Species 0.000 claims description 15
- 108090000790 Enzymes Proteins 0.000 claims description 13
- 102000004190 Enzymes Human genes 0.000 claims description 13
- 150000001733 carboxylic acid esters Chemical class 0.000 claims description 13
- 229940088598 enzyme Drugs 0.000 claims description 13
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 11
- 238000006460 hydrolysis reaction Methods 0.000 claims description 9
- 241000222120 Candida <Saccharomycetales> Species 0.000 claims description 8
- 230000007062 hydrolysis Effects 0.000 claims description 8
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 7
- 108090001060 Lipase Proteins 0.000 claims description 6
- 102000004882 Lipase Human genes 0.000 claims description 6
- 241000228212 Aspergillus Species 0.000 claims description 4
- 108090000371 Esterases Proteins 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 241000589158 Agrobacterium Species 0.000 claims description 3
- 241000588986 Alcaligenes Species 0.000 claims description 3
- 241000193830 Bacillus <bacterium> Species 0.000 claims description 3
- 241000186359 Mycobacterium Species 0.000 claims description 3
- 108010019160 Pancreatin Proteins 0.000 claims description 3
- 241000589516 Pseudomonas Species 0.000 claims description 3
- 108010027597 alpha-chymotrypsin Proteins 0.000 claims description 3
- 229940055695 pancreatin Drugs 0.000 claims description 3
- 241000186361 Actinobacteria <class> Species 0.000 claims description 2
- 241000894006 Bacteria Species 0.000 claims description 2
- 241000233866 Fungi Species 0.000 claims description 2
- 240000004808 Saccharomyces cerevisiae Species 0.000 claims description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 43
- 238000006243 chemical reaction Methods 0.000 description 22
- ODXYWRPJDYJIPT-UHFFFAOYSA-N methyl beta-(acetylthio)isobutyrate Chemical compound COC(=O)C(C)CSC(C)=O ODXYWRPJDYJIPT-UHFFFAOYSA-N 0.000 description 22
- 239000000284 extract Substances 0.000 description 18
- 150000002148 esters Chemical class 0.000 description 17
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
- VFVHNRJEYQGRGE-UHFFFAOYSA-N 3-acetylsulfanyl-2-methylpropanoic acid Chemical compound OC(=O)C(C)CSC(C)=O VFVHNRJEYQGRGE-UHFFFAOYSA-N 0.000 description 14
- 239000012531 culture fluid Substances 0.000 description 14
- 230000003287 optical effect Effects 0.000 description 14
- 239000012429 reaction media Substances 0.000 description 11
- 239000000243 solution Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- 239000008367 deionised water Substances 0.000 description 8
- 229910021641 deionized water Inorganic materials 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 8
- 239000001888 Peptone Substances 0.000 description 7
- 108010080698 Peptones Proteins 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 235000019319 peptone Nutrition 0.000 description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 239000008055 phosphate buffer solution Substances 0.000 description 6
- 238000005119 centrifugation Methods 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 239000004367 Lipase Substances 0.000 description 4
- 241000589776 Pseudomonas putida Species 0.000 description 4
- 239000006285 cell suspension Substances 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- 235000019421 lipase Nutrition 0.000 description 4
- 235000013372 meat Nutrition 0.000 description 4
- 230000007935 neutral effect Effects 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 241000187654 Nocardia Species 0.000 description 3
- 241000589540 Pseudomonas fluorescens Species 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 229940041514 candida albicans extract Drugs 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- 239000008103 glucose Substances 0.000 description 3
- 239000001963 growth medium Substances 0.000 description 3
- 230000003301 hydrolyzing effect Effects 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000013014 purified material Substances 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 150000007970 thio esters Chemical class 0.000 description 3
- 239000012138 yeast extract Substances 0.000 description 3
- 241000589155 Agrobacterium tumefaciens Species 0.000 description 2
- 241000588813 Alcaligenes faecalis Species 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 244000063299 Bacillus subtilis Species 0.000 description 2
- 235000014469 Bacillus subtilis Nutrition 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 241000187481 Mycobacterium phlei Species 0.000 description 2
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 2
- 108091005804 Peptidases Proteins 0.000 description 2
- 102000035195 Peptidases Human genes 0.000 description 2
- 239000004365 Protease Substances 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 239000011149 active material Substances 0.000 description 2
- 238000005273 aeration Methods 0.000 description 2
- 229940005347 alcaligenes faecalis Drugs 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000003262 carboxylic acid ester group Chemical group [H]C([H])([*:2])OC(=O)C([H])([H])[*:1] 0.000 description 2
- 239000012295 chemical reaction liquid Substances 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 230000000813 microbial effect Effects 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- 229940055036 mycobacterium phlei Drugs 0.000 description 2
- 230000003472 neutralizing effect Effects 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 238000010626 work up procedure Methods 0.000 description 2
- CFPHMAVQAJGVPV-UHFFFAOYSA-N 2-sulfanylbutanoic acid Chemical class CCC(S)C(O)=O CFPHMAVQAJGVPV-UHFFFAOYSA-N 0.000 description 1
- 241000131386 Aspergillus sojae Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 241000222175 Diutina rugosa Species 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- -1 Ester compounds Chemical class 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000009395 breeding Methods 0.000 description 1
- 230000001488 breeding effect Effects 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- 230000004663 cell proliferation Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- QVZZVRRYGFTWFH-UHFFFAOYSA-N cyclohept-2-en-1-yl acetate Chemical compound CC(=O)OC1CCCCC=C1 QVZZVRRYGFTWFH-UHFFFAOYSA-N 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- QRFBIEZLXPPQSV-UHFFFAOYSA-N methyl 2-methyl-3-(2-phenylacetyl)sulfanylpropanoate Chemical compound COC(=O)C(C)CSC(=O)CC1=CC=CC=C1 QRFBIEZLXPPQSV-UHFFFAOYSA-N 0.000 description 1
- ZERPWJMPLLLIIK-UHFFFAOYSA-N methyl 3-benzoylsulfanyl-2-methylpropanoate Chemical compound COC(=O)C(C)CSC(=O)C1=CC=CC=C1 ZERPWJMPLLLIIK-UHFFFAOYSA-N 0.000 description 1
- BECGSBWTFYFALC-UHFFFAOYSA-N methyl 4-acetylsulfanyl-2-methylbutanoate Chemical compound COC(=O)C(C)CCSC(C)=O BECGSBWTFYFALC-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 210000004923 pancreatic tissue Anatomy 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000002250 progressing effect Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- TXYPHYOYPVSHNN-UHFFFAOYSA-N s-cyclohept-2-en-1-yl ethanethioate Chemical compound CC(=O)SC1CCCCC=C1 TXYPHYOYPVSHNN-UHFFFAOYSA-N 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- UQDJGEHQDNVPGU-UHFFFAOYSA-N serine phosphoethanolamine Chemical compound [NH3+]CCOP([O-])(=O)OCC([NH3+])C([O-])=O UQDJGEHQDNVPGU-UHFFFAOYSA-N 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 108010079522 solysime Proteins 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 238000009423 ventilation Methods 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 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
- C12P41/00—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture
-
- 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
- C12P11/00—Preparation of sulfur-containing organic compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Zoology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Biotechnology (AREA)
- Microbiology (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (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 (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12028283A JPS6012993A (ja) | 1983-07-04 | 1983-07-04 | 光学活性カルボン酸の製造法 |
| JP58120281A JPH0632633B2 (ja) | 1983-07-04 | 1983-07-04 | 光学活性カルボン酸の製造法 |
| JP13947883A JPS6030692A (ja) | 1983-08-01 | 1983-08-01 | 光学活性カルボン酸の製造法 |
| JP58199943A JPH0632634B2 (ja) | 1983-10-27 | 1983-10-27 | 光学活性カルボン酸エステルの製造法 |
| JP24578483A JPS60141297A (ja) | 1983-12-28 | 1983-12-28 | 光学活性カルボン酸及びその対掌体エステルの製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3424440A1 DE3424440A1 (de) | 1985-01-17 |
| DE3424440C2 true DE3424440C2 (en:Method) | 1990-04-12 |
Family
ID=27526873
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19843424440 Granted DE3424440A1 (de) | 1983-07-04 | 1984-07-03 | Verfahren zur herstellung optisch aktiver carbonsaeuren und deren ester in form der optischen antipoden |
Country Status (3)
| Country | Link |
|---|---|
| US (1) | US4629701A (en:Method) |
| EP (1) | EP0130752B1 (en:Method) |
| DE (1) | DE3424440A1 (en:Method) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0130752B1 (en) * | 1983-07-04 | 1991-02-27 | Mitsubishi Rayon Co., Ltd. | Process for preparing optically active carboxylic acids and antipode esters thereof |
| JPS61227797A (ja) * | 1985-04-01 | 1986-10-09 | Kanegafuchi Chem Ind Co Ltd | 光学活性グリコ−ル類の製造方法 |
| JPS61280294A (ja) * | 1985-06-04 | 1986-12-10 | Nisshin Flour Milling Co Ltd | 光学活性カルバサイクリン中間体の製造方法 |
| GB8514489D0 (en) * | 1985-06-07 | 1985-07-10 | Shell Int Research | Producing 2-arylpropionic acids |
| EP0259465A1 (en) * | 1986-03-07 | 1988-03-16 | Wisconsin Alumni Research Foundation | Process for preparing optically-active 3-acylthio-2-methylpropionic acid derivatives |
| US4857469A (en) * | 1987-04-09 | 1989-08-15 | Toyo Jozo Co., Ltd. | Process for preparing optically active mercapto compound |
| DE3727243A1 (de) * | 1987-08-15 | 1989-02-23 | Hoechst Ag | Verfahren zur enzymatischen herstellung optisch aktiver phosphorhaltiger funktioneller essigsaeurederivate |
| US5057427A (en) * | 1988-04-07 | 1991-10-15 | Sepracor, Inc. | Method for resolution of stereoisomers |
| IT1217765B (it) * | 1988-06-02 | 1990-03-30 | Montedison Spa | Processo per la risoluzione enzimatica degli isomeri ottici di derivati racemi esterei dell,acido 3 mercapto 2 alchilpropionico |
| US5177006A (en) * | 1988-07-14 | 1993-01-05 | E. R. Squibb & Sons, Inc. | Enzymatic resolution process |
| CA1318627C (en) * | 1988-07-14 | 1993-06-01 | Jeffrey M. Howell | Enzymatic resolution process |
| US5128263A (en) * | 1988-07-14 | 1992-07-07 | E. R. Squibb & Sons, Inc. | Enzymatic resolution process hydrolyzing thio-ester |
| US5232852A (en) * | 1989-03-23 | 1993-08-03 | Hoffmann-La Roche Inc. | Process for the production of dioxolanes |
| US4912042A (en) * | 1989-08-17 | 1990-03-27 | Eastman Kodak Company | Preparation of D-malic acid or derivative |
| US4921798A (en) * | 1989-09-25 | 1990-05-01 | Eastman Kodak Company | Synthesis of (aryl or arylalkyl)-3-hydroxy propionic acids and aryl alkanediols having high optical purity |
| CA2023856A1 (en) * | 1989-09-26 | 1991-03-27 | Jeffrey M. Howell | Enzymatic resolution process |
| US5420037A (en) * | 1989-09-26 | 1995-05-30 | E. R. Squibb & Sons, Inc. | Process for separation of enantiomeric 3-mercapto-2-substituted alkanoic acid using lipase P30 and synthesis of captopril type compounds |
| US5149855A (en) * | 1989-12-26 | 1992-09-22 | Mitsubishi Rayon Co., Ltd. | Process for racemizing optically active carboxylic acid esters |
| EP0475255A3 (en) * | 1990-09-12 | 1993-04-14 | F. Hoffmann-La Roche Ag | Process for the preparation of optically pure (s)-alpha-((tert-butylsulfonyl)methyl)hydro cinnamic acid |
| US5106736A (en) * | 1991-04-23 | 1992-04-21 | E.R. Squibb & Sons, Inc. | Enzymatic process for enantiomer-specific perparation of mercapto alkanoic acid compounds |
| US5308765A (en) * | 1991-05-15 | 1994-05-03 | Mitsubishi Rayon Co., Ltd. | Esterase genes, esterase, recombinant plasmids and transformants containing the recombinant plasmid and methods of producing optically acitve carboxylic acids and their enantiomeric esters using said transformants |
| JPWO2003097851A1 (ja) * | 2002-05-15 | 2005-09-15 | 小野薬品工業株式会社 | 光学活性アルキルカルボン酸誘導体の製造方法 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4094741A (en) * | 1976-02-04 | 1978-06-13 | Kanegafuchi Kagaku Kogyo Kabushiki Kaisha | Process for preparing D-(-)-N-carbamoyl-2-(phenyl or substituted phenyl)glycines |
| JPS5366493A (en) * | 1976-11-19 | 1978-06-13 | Banyu Pharmaceut Co Ltd | Optical resolution of dl-phenylglycineamides |
| NL7809121A (nl) * | 1978-09-07 | 1980-03-11 | Oce Andeno B V Grubbenvorsterw | Optisch aktieve derivaten van mercapto-isoboterzuur. |
| JPS55118455A (en) * | 1979-03-02 | 1980-09-11 | Sumitomo Chem Co Ltd | Method of collecting optically active d-alpha-methyl-beta- mercapto propionic acid derivative |
| JPS5681557A (en) * | 1979-12-07 | 1981-07-03 | Sumitomo Chem Co Ltd | Preparation of optically active alpha-methyl-beta- mercaptopropionic acid derivative |
| US4294775A (en) * | 1980-03-03 | 1981-10-13 | Ethyl Corporation | Resolution of acylated D,L-alkyl substituted alkanoic acids |
| JPS57188563A (en) * | 1981-05-15 | 1982-11-19 | Tanabe Seiyaku Co Ltd | Preparation of optically active 3-benzoylthio-2-methyl- propionic acid |
| US4452897A (en) * | 1982-06-14 | 1984-06-05 | Takara Shuzo Co., Ltd. | Method of preparing optically active β-(S)-aminoglutaric acid monoalkyl esters |
| EP0130752B1 (en) * | 1983-07-04 | 1991-02-27 | Mitsubishi Rayon Co., Ltd. | Process for preparing optically active carboxylic acids and antipode esters thereof |
-
1984
- 1984-06-22 EP EP84304238A patent/EP0130752B1/en not_active Expired
- 1984-07-02 US US06/627,093 patent/US4629701A/en not_active Expired - Lifetime
- 1984-07-03 DE DE19843424440 patent/DE3424440A1/de active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| EP0130752A2 (en) | 1985-01-09 |
| DE3424440A1 (de) | 1985-01-17 |
| US4629701A (en) | 1986-12-16 |
| EP0130752A3 (en) | 1986-10-01 |
| EP0130752B1 (en) | 1991-02-27 |
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