CA1206435A - Preparation de l-phenylalanine par reutilisation de la phenylalanine ammoniac lyase - Google Patents
Preparation de l-phenylalanine par reutilisation de la phenylalanine ammoniac lyaseInfo
- Publication number
- CA1206435A CA1206435A CA000435596A CA435596A CA1206435A CA 1206435 A CA1206435 A CA 1206435A CA 000435596 A CA000435596 A CA 000435596A CA 435596 A CA435596 A CA 435596A CA 1206435 A CA1206435 A CA 1206435A
- Authority
- CA
- Canada
- Prior art keywords
- phenylalanine
- ammonium
- substrate solution
- acid
- column
- 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
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 title claims abstract description 93
- 238000000034 method Methods 0.000 title claims abstract description 76
- 108700023158 Phenylalanine ammonia-lyases Proteins 0.000 title claims abstract description 58
- 229960005190 phenylalanine Drugs 0.000 title claims abstract description 49
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 6
- WBYWAXJHAXSJNI-VOTSOKGWSA-N trans-cinnamic acid Chemical compound OC(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-N 0.000 claims abstract description 18
- 239000000758 substrate Substances 0.000 claims description 57
- 239000000243 solution Substances 0.000 claims description 53
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 30
- -1 ammonium ions Chemical class 0.000 claims description 18
- 239000002253 acid Substances 0.000 claims description 17
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 15
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 14
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 12
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 claims description 8
- 150000003863 ammonium salts Chemical class 0.000 claims description 7
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 claims description 7
- 229910052921 ammonium sulfate Inorganic materials 0.000 claims description 7
- 235000011130 ammonium sulphate Nutrition 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 7
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 6
- PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 claims description 4
- YWYZEGXAUVWDED-UHFFFAOYSA-N triammonium citrate Chemical compound [NH4+].[NH4+].[NH4+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O YWYZEGXAUVWDED-UHFFFAOYSA-N 0.000 claims description 4
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 claims description 3
- 239000005695 Ammonium acetate Substances 0.000 claims description 3
- 239000004254 Ammonium phosphate Substances 0.000 claims description 3
- 229940043376 ammonium acetate Drugs 0.000 claims description 3
- 235000019257 ammonium acetate Nutrition 0.000 claims description 3
- 229910000148 ammonium phosphate Inorganic materials 0.000 claims description 3
- 235000019289 ammonium phosphates Nutrition 0.000 claims description 3
- MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 claims description 3
- 150000002500 ions Chemical class 0.000 claims description 3
- 239000012670 alkaline solution Substances 0.000 claims description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract description 29
- 230000000694 effects Effects 0.000 abstract description 19
- 229910021529 ammonia Inorganic materials 0.000 abstract description 10
- 239000003054 catalyst Substances 0.000 abstract description 4
- 210000004027 cell Anatomy 0.000 description 33
- 239000002609 medium Substances 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 11
- 102000004190 Enzymes Human genes 0.000 description 9
- 108090000790 Enzymes Proteins 0.000 description 9
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 9
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical group [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 241000223254 Rhodotorula mucilaginosa Species 0.000 description 7
- 230000001939 inductive effect Effects 0.000 description 6
- 210000001822 immobilized cell Anatomy 0.000 description 5
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 description 5
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 235000019270 ammonium chloride Nutrition 0.000 description 4
- 239000000908 ammonium hydroxide Substances 0.000 description 4
- 230000003197 catalytic effect Effects 0.000 description 4
- 230000014759 maintenance of location Effects 0.000 description 4
- 229910000069 nitrogen hydride Inorganic materials 0.000 description 4
- 238000000855 fermentation Methods 0.000 description 3
- 230000004151 fermentation Effects 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 2
- 108010008292 L-Amino Acid Oxidase Proteins 0.000 description 2
- 102000007070 L-amino-acid oxidase Human genes 0.000 description 2
- 229930182844 L-isoleucine Natural products 0.000 description 2
- 239000001888 Peptone Substances 0.000 description 2
- 108010080698 Peptones Proteins 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 238000003556 assay Methods 0.000 description 2
- 229930016911 cinnamic acid Natural products 0.000 description 2
- 235000013985 cinnamic acid Nutrition 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 238000007824 enzymatic assay Methods 0.000 description 2
- 230000000977 initiatory effect Effects 0.000 description 2
- 229960000310 isoleucine Drugs 0.000 description 2
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 2
- 235000019319 peptone Nutrition 0.000 description 2
- 235000008729 phenylalanine Nutrition 0.000 description 2
- 239000013587 production medium Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000000717 retained effect Effects 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 101710169152 L-amino oxidase Proteins 0.000 description 1
- AGPKZVBTJJNPAG-WHFBIAKZSA-N L-isoleucine Chemical compound CC[C@H](C)[C@H](N)C(O)=O AGPKZVBTJJNPAG-WHFBIAKZSA-N 0.000 description 1
- 108090000942 Lactalbumin Proteins 0.000 description 1
- 102000004407 Lactalbumin Human genes 0.000 description 1
- UQONAEXHTGDOIH-AWEZNQCLSA-N O=C(N1CC[C@@H](C1)N1CCCC1=O)C1=CC2=C(NC3(CC3)CCO2)N=C1 Chemical compound O=C(N1CC[C@@H](C1)N1CCCC1=O)C1=CC2=C(NC3(CC3)CCO2)N=C1 UQONAEXHTGDOIH-AWEZNQCLSA-N 0.000 description 1
- 108010058846 Ovalbumin Proteins 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- PBLWYVAEJYQTLU-UHFFFAOYSA-N azanium;3-phenylprop-2-enoate Chemical compound [NH4+].[O-]C(=O)C=CC1=CC=CC=C1 PBLWYVAEJYQTLU-UHFFFAOYSA-N 0.000 description 1
- 210000003719 b-lymphocyte Anatomy 0.000 description 1
- 229940041514 candida albicans extract Drugs 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000012258 culturing Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 235000020776 essential amino acid Nutrition 0.000 description 1
- 239000003797 essential amino acid Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 238000003306 harvesting Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000006916 nutrient agar Substances 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 230000035764 nutrition Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 229940092253 ovalbumin Drugs 0.000 description 1
- 238000010979 pH adjustment Methods 0.000 description 1
- 229940023462 paste product Drugs 0.000 description 1
- BULVZWIRKLYCBC-UHFFFAOYSA-N phorate Chemical compound CCOP(=S)(OCC)SCSCC BULVZWIRKLYCBC-UHFFFAOYSA-N 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000012138 yeast extract Substances 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
- C12P13/22—Tryptophan; Tyrosine; Phenylalanine; 3,4-Dihydroxyphenylalanine
- C12P13/222—Phenylalanine
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (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)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Immobilizing And Processing Of Enzymes And Microorganisms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US43218282A | 1982-10-01 | 1982-10-01 | |
| US432,182 | 1982-10-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1206435A true CA1206435A (fr) | 1986-06-24 |
Family
ID=23715088
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000435596A Expired CA1206435A (fr) | 1982-10-01 | 1983-08-29 | Preparation de l-phenylalanine par reutilisation de la phenylalanine ammoniac lyase |
Country Status (21)
| Country | Link |
|---|---|
| JP (1) | JPS5991890A (fr) |
| AU (1) | AU1864883A (fr) |
| BE (2) | BE897889A (fr) |
| BR (1) | BR8305366A (fr) |
| CA (1) | CA1206435A (fr) |
| CH (1) | CH658670A5 (fr) |
| DD (1) | DD217822A5 (fr) |
| DE (1) | DE3333246A1 (fr) |
| DK (1) | DK452783A (fr) |
| ES (1) | ES526165A1 (fr) |
| FI (1) | FI833552A (fr) |
| FR (1) | FR2533941B1 (fr) |
| GB (1) | GB2127821B (fr) |
| GR (1) | GR79053B (fr) |
| IL (1) | IL69672A0 (fr) |
| IT (1) | IT8368017A0 (fr) |
| LU (1) | LU85019A1 (fr) |
| NL (1) | NL8303369A (fr) |
| PL (1) | PL243972A1 (fr) |
| SE (1) | SE8305151L (fr) |
| ZA (1) | ZA836626B (fr) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4600692A (en) * | 1983-02-10 | 1986-07-15 | Purification Engineering, Inc. | Immobilized cells for preparing phenylalanine |
| EP0165757A3 (fr) * | 1984-06-11 | 1987-07-22 | Genex Corporation | Production de L-pnénylalanine |
| JPS61247395A (ja) * | 1985-04-23 | 1986-11-04 | Mitsui Toatsu Chem Inc | Ｌ−フェニルアラニンの製造法 |
| JP2931623B2 (ja) * | 1990-04-20 | 1999-08-09 | 三井化学株式会社 | Ｌ‐フェニルアラニンの製造方法 |
| JPH0739815Y2 (ja) * | 1991-06-14 | 1995-09-13 | 東洋製罐株式会社 | ワンタッチで開閉可能なアーチ状キャップ |
| US5981239A (en) * | 1997-09-24 | 1999-11-09 | Great Lakes Chemical Corp. | Synthesis of optically active phenylalanine analogs using Rhodotorula graminis |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5015955A (fr) * | 1973-06-15 | 1975-02-20 | ||
| ES433764A1 (es) * | 1974-02-22 | 1976-12-01 | Pfizer | Un procedimiento para preparar 1-fenilalanina. |
| JPS5922516B2 (ja) * | 1977-01-31 | 1984-05-26 | 田辺製薬株式会社 | Ｌ−フエニルアラニンの製造法 |
| JPS5626197A (en) * | 1979-08-09 | 1981-03-13 | Tanabe Seiyaku Co Ltd | Preparation of l-phenylalanine |
| US4434228A (en) * | 1982-04-20 | 1984-02-28 | Genex Corporation | Immobilization of biological materials in condensed polyalkyleneimine polymers |
| US4504582A (en) * | 1982-07-20 | 1985-03-12 | Genex Corporation | Vermiculite as a carrier support for immobilized biological materials |
-
1983
- 1983-08-29 CA CA000435596A patent/CA1206435A/fr not_active Expired
- 1983-09-02 AU AU18648/83A patent/AU1864883A/en not_active Abandoned
- 1983-09-06 IL IL69672A patent/IL69672A0/xx unknown
- 1983-09-06 ZA ZA836626A patent/ZA836626B/xx unknown
- 1983-09-14 DE DE19833333246 patent/DE3333246A1/de not_active Withdrawn
- 1983-09-15 GR GR72447A patent/GR79053B/el unknown
- 1983-09-23 SE SE8305151A patent/SE8305151L/ not_active Application Discontinuation
- 1983-09-26 FR FR8315229A patent/FR2533941B1/fr not_active Expired
- 1983-09-27 GB GB08325797A patent/GB2127821B/en not_active Expired
- 1983-09-28 LU LU85019A patent/LU85019A1/fr unknown
- 1983-09-29 BR BR8305366A patent/BR8305366A/pt unknown
- 1983-09-30 ES ES526165A patent/ES526165A1/es not_active Expired
- 1983-09-30 FI FI833552A patent/FI833552A/fi not_active Application Discontinuation
- 1983-09-30 BE BE0/211627A patent/BE897889A/fr not_active IP Right Cessation
- 1983-09-30 PL PL24397283A patent/PL243972A1/xx unknown
- 1983-09-30 NL NL8303369A patent/NL8303369A/nl not_active Application Discontinuation
- 1983-09-30 IT IT8368017A patent/IT8368017A0/it unknown
- 1983-09-30 CH CH5328/83A patent/CH658670A5/de not_active IP Right Cessation
- 1983-09-30 DD DD83255308A patent/DD217822A5/de unknown
- 1983-09-30 DK DK452783A patent/DK452783A/da not_active Application Discontinuation
- 1983-10-01 JP JP58184356A patent/JPS5991890A/ja active Pending
-
1985
- 1985-03-14 BE BE0/214649A patent/BE901938R/fr not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| IL69672A0 (en) | 1983-12-30 |
| IT8368017A0 (it) | 1983-09-30 |
| JPS5991890A (ja) | 1984-05-26 |
| GB8325797D0 (en) | 1983-10-26 |
| NL8303369A (nl) | 1984-05-01 |
| SE8305151L (sv) | 1984-04-02 |
| ZA836626B (en) | 1984-05-30 |
| ES526165A1 (es) | 1985-05-01 |
| DE3333246A1 (de) | 1984-04-05 |
| GR79053B (fr) | 1984-10-02 |
| CH658670A5 (de) | 1986-11-28 |
| BE897889A (fr) | 1984-01-16 |
| DK452783A (da) | 1984-04-02 |
| BR8305366A (pt) | 1984-05-08 |
| DK452783D0 (da) | 1983-09-30 |
| DD217822A5 (de) | 1985-01-23 |
| GB2127821A (en) | 1984-04-18 |
| FI833552A0 (fi) | 1983-09-30 |
| FR2533941B1 (fr) | 1988-02-05 |
| LU85019A1 (fr) | 1984-03-16 |
| SE8305151D0 (sv) | 1983-09-23 |
| AU1864883A (en) | 1984-04-05 |
| GB2127821B (en) | 1986-04-30 |
| FI833552A (fi) | 1984-04-02 |
| PL243972A1 (en) | 1984-07-30 |
| FR2533941A1 (fr) | 1984-04-06 |
| BE901938R (fr) | 1985-07-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry | ||
| MKEX | Expiry |
Effective date: 20030829 |