JPS6043958B2 - Ｌ−α−アミノ酸およびＤ−α−アミノ酸アミドの製造方法 - Google Patents
Ｌ−α−アミノ酸およびＤ−α−アミノ酸アミドの製造方法Info
- Publication number
- JPS6043958B2 JPS6043958B2 JP52001122A JP112277A JPS6043958B2 JP S6043958 B2 JPS6043958 B2 JP S6043958B2 JP 52001122 A JP52001122 A JP 52001122A JP 112277 A JP112277 A JP 112277A JP S6043958 B2 JPS6043958 B2 JP S6043958B2
- Authority
- JP
- Japan
- Prior art keywords
- amino acid
- acid amide
- preparation
- producing
- phenylglycinamide
- 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
- 150000007650 D alpha amino acids Chemical class 0.000 title claims description 9
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- 150000007649 L alpha amino acids Chemical class 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 claims description 21
- 241000589776 Pseudomonas putida Species 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 16
- 244000005700 microbiome Species 0.000 claims description 12
- 230000000694 effects Effects 0.000 claims description 11
- ZGUNAGUHMKGQNY-ZETCQYMHSA-N L-alpha-phenylglycine zwitterion Chemical compound OC(=O)[C@@H](N)C1=CC=CC=C1 ZGUNAGUHMKGQNY-ZETCQYMHSA-N 0.000 claims description 9
- 238000012258 culturing Methods 0.000 claims description 7
- 241000589516 Pseudomonas Species 0.000 claims description 6
- KIYRSYYOVDHSPG-SSDOTTSWSA-N (2r)-2-amino-2-phenylacetamide Chemical compound NC(=O)[C@H](N)C1=CC=CC=C1 KIYRSYYOVDHSPG-SSDOTTSWSA-N 0.000 claims description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- 235000015097 nutrients Nutrition 0.000 claims description 4
- 150000001408 amides Chemical class 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- KIYRSYYOVDHSPG-UHFFFAOYSA-N 2-amino-2-phenylacetamide Chemical compound NC(=O)C(N)C1=CC=CC=C1 KIYRSYYOVDHSPG-UHFFFAOYSA-N 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims 1
- 229910052698 phosphorus Inorganic materials 0.000 claims 1
- 239000011574 phosphorus Substances 0.000 claims 1
- 102000004190 Enzymes Human genes 0.000 description 19
- 108090000790 Enzymes Proteins 0.000 description 19
- 229940088598 enzyme Drugs 0.000 description 19
- 210000004027 cell Anatomy 0.000 description 18
- 239000000243 solution Substances 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- 239000000284 extract Substances 0.000 description 11
- 235000001014 amino acid Nutrition 0.000 description 10
- 229940024606 amino acid Drugs 0.000 description 10
- 150000001413 amino acids Chemical class 0.000 description 10
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 8
- KIYRSYYOVDHSPG-ZETCQYMHSA-N (2s)-2-amino-2-phenylacetamide Chemical compound NC(=O)[C@@H](N)C1=CC=CC=C1 KIYRSYYOVDHSPG-ZETCQYMHSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 5
- 230000007062 hydrolysis Effects 0.000 description 5
- 238000006460 hydrolysis reaction Methods 0.000 description 5
- DCXYFEDJOCDNAF-UHFFFAOYSA-N Asparagine Natural products OC(=O)C(N)CC(N)=O DCXYFEDJOCDNAF-UHFFFAOYSA-N 0.000 description 4
- IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 4
- 235000008206 alpha-amino acids Nutrition 0.000 description 4
- 229910001629 magnesium chloride Inorganic materials 0.000 description 4
- 239000002609 medium Substances 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 150000001370 alpha-amino acid derivatives Chemical class 0.000 description 3
- 235000009582 asparagine Nutrition 0.000 description 3
- 229960001230 asparagine Drugs 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000001963 growth medium Substances 0.000 description 3
- 229960002510 mandelic acid Drugs 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 238000001694 spray drying Methods 0.000 description 3
- TZADAWVLFGIAKY-UHFFFAOYSA-N 2-amino-2-(4-methoxyphenyl)acetamide Chemical compound COC1=CC=C(C(N)C(N)=O)C=C1 TZADAWVLFGIAKY-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 108700023418 Amidases Proteins 0.000 description 2
- 241000228230 Aspergillus parasiticus Species 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- LJCWONGJFPCTTL-ZETCQYMHSA-N L-4-hydroxyphenylglycine Chemical compound OC(=O)[C@@H](N)C1=CC=C(O)C=C1 LJCWONGJFPCTTL-ZETCQYMHSA-N 0.000 description 2
- DCXYFEDJOCDNAF-REOHCLBHSA-N L-asparagine Chemical compound OC(=O)[C@@H](N)CC(N)=O DCXYFEDJOCDNAF-REOHCLBHSA-N 0.000 description 2
- FORGMRSGVSYZQR-YFKPBYRVSA-N L-leucinamide Chemical compound CC(C)C[C@H](N)C(N)=O FORGMRSGVSYZQR-YFKPBYRVSA-N 0.000 description 2
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 2
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 102000005922 amidase Human genes 0.000 description 2
- 230000003698 anagen phase Effects 0.000 description 2
- 239000012736 aqueous medium Substances 0.000 description 2
- 210000002421 cell wall Anatomy 0.000 description 2
- 239000012531 culture fluid Substances 0.000 description 2
- 229940079919 digestives enzyme preparation Drugs 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 230000012010 growth Effects 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052748 manganese Inorganic materials 0.000 description 2
- 239000011572 manganese Substances 0.000 description 2
- 239000008363 phosphate buffer Substances 0.000 description 2
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 230000000707 stereoselective effect Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- WQFROZWIRZWMFE-UHFFFAOYSA-N 2-(p-hydroxyphenyl)glycinamide Chemical compound NC(=O)C(N)C1=CC=C(O)C=C1 WQFROZWIRZWMFE-UHFFFAOYSA-N 0.000 description 1
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 240000006439 Aspergillus oryzae Species 0.000 description 1
- 235000002247 Aspergillus oryzae Nutrition 0.000 description 1
- 244000063299 Bacillus subtilis Species 0.000 description 1
- 235000014469 Bacillus subtilis Nutrition 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 150000008574 D-amino acids Chemical class 0.000 description 1
- 241000193385 Geobacillus stearothermophilus Species 0.000 description 1
- 150000008575 L-amino acids Chemical class 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 229910021380 Manganese Chloride Inorganic materials 0.000 description 1
- GLFNIEUTAYBVOC-UHFFFAOYSA-L Manganese chloride Chemical compound Cl[Mn]Cl GLFNIEUTAYBVOC-UHFFFAOYSA-L 0.000 description 1
- 241000187481 Mycobacterium phlei Species 0.000 description 1
- 241000425347 Phyla <beetle> Species 0.000 description 1
- 241000589517 Pseudomonas aeruginosa Species 0.000 description 1
- 241000589540 Pseudomonas fluorescens Species 0.000 description 1
- 241000589614 Pseudomonas stutzeri Species 0.000 description 1
- 241000607269 Vibrio proteolyticus Species 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001371 alpha-amino acids Chemical class 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- LLSDKQJKOVVTOJ-UHFFFAOYSA-L calcium chloride dihydrate Chemical compound O.O.[Cl-].[Cl-].[Ca+2] LLSDKQJKOVVTOJ-UHFFFAOYSA-L 0.000 description 1
- 229940052299 calcium chloride dihydrate Drugs 0.000 description 1
- 229940041514 candida albicans extract Drugs 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- UFMZWBIQTDUYBN-UHFFFAOYSA-N cobalt dinitrate Chemical compound [Co+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O UFMZWBIQTDUYBN-UHFFFAOYSA-N 0.000 description 1
- 229910001981 cobalt nitrate Inorganic materials 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 description 1
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
- 229910000397 disodium phosphate Inorganic materials 0.000 description 1
- 235000019800 disodium phosphate Nutrition 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000003102 growth factor Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 239000000411 inducer Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- SURQXAFEQWPFPV-UHFFFAOYSA-L iron(2+) sulfate heptahydrate Chemical compound O.O.O.O.O.O.O.[Fe+2].[O-]S([O-])(=O)=O SURQXAFEQWPFPV-UHFFFAOYSA-L 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- WRUGWIBCXHJTDG-UHFFFAOYSA-L magnesium sulfate heptahydrate Chemical compound O.O.O.O.O.O.O.[Mg+2].[O-]S([O-])(=O)=O WRUGWIBCXHJTDG-UHFFFAOYSA-L 0.000 description 1
- 229940061634 magnesium sulfate heptahydrate Drugs 0.000 description 1
- 239000011565 manganese chloride Substances 0.000 description 1
- 235000002867 manganese chloride Nutrition 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229940055036 mycobacterium phlei Drugs 0.000 description 1
- MGFYIUFZLHCRTH-UHFFFAOYSA-N nitrilotriacetic acid Chemical compound OC(=O)CN(CC(O)=O)CC(O)=O MGFYIUFZLHCRTH-UHFFFAOYSA-N 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 230000010349 pulsation Effects 0.000 description 1
- 230000006340 racemization Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time 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
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 239000012138 yeast extract Substances 0.000 description 1
- 150000003752 zinc compounds Chemical class 0.000 description 1
- 229910000368 zinc sulfate Inorganic materials 0.000 description 1
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 1
- 229960001763 zinc sulfate Drugs 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)
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S435/00—Chemistry: molecular biology and microbiology
- Y10S435/8215—Microorganisms
- Y10S435/822—Microorganisms using bacteria or actinomycetales
- Y10S435/874—Pseudomonas
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S435/00—Chemistry: molecular biology and microbiology
- Y10S435/8215—Microorganisms
- Y10S435/822—Microorganisms using bacteria or actinomycetales
- Y10S435/874—Pseudomonas
- Y10S435/877—Pseudomonas putida
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Zoology (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Microbiology (AREA)
- Biotechnology (AREA)
- Biochemistry (AREA)
- General Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Biomedical Technology (AREA)
- Molecular Biology (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Enzymes And Modification Thereof (AREA)
- Micro-Organisms Or Cultivation Processes Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| LU74142 | 1976-01-08 | ||
| LU74142A LU74142A1 (en]) | 1976-01-08 | 1976-01-08 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5294486A JPS5294486A (en) | 1977-08-09 |
| JPS6043958B2 true JPS6043958B2 (ja) | 1985-10-01 |
Family
ID=19728133
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP52001122A Expired JPS6043958B2 (ja) | 1976-01-08 | 1977-01-08 | Ｌ−α−アミノ酸およびＤ−α−アミノ酸アミドの製造方法 |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US4080259A (en]) |
| JP (1) | JPS6043958B2 (en]) |
| BE (1) | BE850177A (en]) |
| CH (1) | CH638241A5 (en]) |
| DE (1) | DE2700456A1 (en]) |
| DK (1) | DK143287C (en]) |
| FR (1) | FR2337761A1 (en]) |
| GB (1) | GB1552542A (en]) |
| LU (1) | LU74142A1 (en]) |
| NL (1) | NL7700092A (en]) |
| SE (1) | SE435731B (en]) |
Families Citing this family (25)
| 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 |
| FR2447359A1 (fr) * | 1979-01-24 | 1980-08-22 | Anvar | Procede de preparation d'acides a-amines optiquement actifs par hydrolyse biologique de nitriles ou d'amides a-amines |
| JPS5713000A (en) * | 1980-06-24 | 1982-01-22 | Ube Ind Ltd | Preparation of optical active tryptophane |
| US4366250A (en) * | 1980-09-24 | 1982-12-28 | Anvar | Preparation process of optically active α-aminated acids by biological hydrolysis of nitriles |
| JPS59146595A (ja) * | 1983-02-10 | 1984-08-22 | Nippon Zeon Co Ltd | Ｓ−アデノシル−ｌ−ホモシステインの製造法 |
| NL8400312A (nl) * | 1984-02-02 | 1985-09-02 | Stamicarbon | Optisch aktief gesubstitueerd boterzuuramide alsmede werkwijze voor de optische scheiding van gesubstitueerd boterzuuramide. |
| JPS60180599A (ja) * | 1984-02-27 | 1985-09-14 | Nippon Zeon Co Ltd | Ｓ−アデノシル−ｌ−ホモシステインの製造法 |
| NL8403093A (nl) * | 1984-10-11 | 1986-05-01 | Stamicarbon | Werkwijze voor de enzymatische hydrolyse van d-alfa-aminozuuramiden. |
| NL8403487A (nl) * | 1984-11-15 | 1986-06-02 | Stamicarbon | Werkwijze voor de enzymatische scheiding van dl-alfa-aminozuuramides. |
| JPS61293394A (ja) * | 1985-06-21 | 1986-12-24 | Mitsubishi Gas Chem Co Inc | Ｌ−α−アミノ酸の製法 |
| JPS6255097A (ja) * | 1985-09-04 | 1987-03-10 | Nitto Chem Ind Co Ltd | Ｌ−アミノ酸の製造法 |
| US5215897A (en) * | 1985-09-04 | 1993-06-01 | Nitto Chemical Industries Co., Ltd. | Process for producing L-amino acids |
| GB8630029D0 (en) * | 1986-12-16 | 1987-01-28 | Ici Plc | Decomposition of acrylamide |
| NL8800224A (nl) * | 1988-01-29 | 1989-08-16 | Stamicarbon | Werkwijze ter bereiding van zwavelhoudende l-alpha-aminozuren. |
| DE3816063A1 (de) * | 1988-05-06 | 1989-11-23 | Schering Ag | Verfahren zur herstellung von l-aminosaeuren und aminosaeure-amiden |
| 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. |
| CA2150526C (en) * | 1994-06-09 | 2005-11-15 | Andreas Kiener | Biotechnological process for the preparation of cyclic s-.alpha.-amino carboxylic acids and r-.alpha.-amino carboxamides |
| JPH11508761A (ja) * | 1995-05-08 | 1999-08-03 | ロンザ アーゲー | Ｒ−α−ピペラジンカルボン酸およびＳ−α−ピペラジンカルボキサミドを製造する生物工学的方法 |
| US20050166498A1 (en) * | 1999-12-17 | 2005-08-04 | Oakey David D. | Carpet tile with cutout section, method and apparatus for production and method of installation |
| JP2004536608A (ja) * | 2001-07-23 | 2004-12-09 | ディーエスエム アイピー アセッツ ビー．ブイ． | 鏡像体選択的アミダーゼをエンコードする核酸配列 |
| WO2004005517A2 (en) * | 2002-07-09 | 2004-01-15 | Degussa Ag | L-amidase from rhizobium huautlense |
| ATE455181T1 (de) | 2004-01-19 | 2010-01-15 | Dsm Ip Assets Bv | Biochemische synthese von 6-aminocapronsäure |
| GB0413322D0 (en) * | 2004-06-15 | 2004-07-14 | Avecia Ltd | Process |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5231031B2 (en]) * | 1973-06-30 | 1977-08-12 | ||
| FR2245585B1 (en]) * | 1973-09-19 | 1976-05-14 | Anvar | |
| FR2294999A1 (fr) * | 1974-12-18 | 1976-07-16 | Anvar | Procede de preparation d'amides par hydrolyse biologique |
-
1976
- 1976-01-08 LU LU74142A patent/LU74142A1/xx unknown
-
1977
- 1977-01-04 US US05/756,969 patent/US4080259A/en not_active Expired - Lifetime
- 1977-01-04 SE SE7700066A patent/SE435731B/xx not_active IP Right Cessation
- 1977-01-06 CH CH13077A patent/CH638241A5/de not_active IP Right Cessation
- 1977-01-06 NL NL7700092A patent/NL7700092A/xx not_active Application Discontinuation
- 1977-01-07 DE DE19772700456 patent/DE2700456A1/de active Granted
- 1977-01-07 BE BE173906A patent/BE850177A/xx not_active IP Right Cessation
- 1977-01-07 DK DK6477A patent/DK143287C/da active
- 1977-01-07 FR FR7700320A patent/FR2337761A1/fr active Granted
- 1977-01-07 GB GB646/77A patent/GB1552542A/en not_active Expired
- 1977-01-08 JP JP52001122A patent/JPS6043958B2/ja not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GB1552542A (en) | 1979-09-12 |
| SE435731B (sv) | 1984-10-15 |
| US4080259A (en) | 1978-03-21 |
| DE2700456C2 (en]) | 1988-11-24 |
| BE850177A (fr) | 1977-05-02 |
| DK6477A (da) | 1977-07-09 |
| LU74142A1 (en]) | 1977-07-22 |
| SE7700066L (sv) | 1977-07-09 |
| NL7700092A (nl) | 1977-07-12 |
| DK143287B (da) | 1981-08-03 |
| CH638241A5 (de) | 1983-09-15 |
| JPS5294486A (en) | 1977-08-09 |
| DK143287C (da) | 1982-01-11 |
| FR2337761B1 (en]) | 1983-08-26 |
| DE2700456A1 (de) | 1977-07-21 |
| FR2337761A1 (fr) | 1977-08-05 |
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