FR2518988A1 - Procede pour preparer la l-threonine - Google Patents
Procede pour preparer la l-threonine Download PDFInfo
- Publication number
- FR2518988A1 FR2518988A1 FR8221816A FR8221816A FR2518988A1 FR 2518988 A1 FR2518988 A1 FR 2518988A1 FR 8221816 A FR8221816 A FR 8221816A FR 8221816 A FR8221816 A FR 8221816A FR 2518988 A1 FR2518988 A1 FR 2518988A1
- Authority
- FR
- France
- Prior art keywords
- threonine
- aldolase
- allothreonine
- solution
- 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.)
- Granted
Links
- AYFVYJQAPQTCCC-GBXIJSLDSA-N L-threonine Chemical compound C[C@@H](O)[C@H](N)C(O)=O AYFVYJQAPQTCCC-GBXIJSLDSA-N 0.000 title claims abstract description 126
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 20
- AYFVYJQAPQTCCC-UHFFFAOYSA-N Threonine Natural products CC(O)C(N)C(O)=O AYFVYJQAPQTCCC-UHFFFAOYSA-N 0.000 claims abstract description 93
- 108010049097 threonine acetaldehyde-lyase Proteins 0.000 claims abstract description 39
- 239000000203 mixture Substances 0.000 claims abstract description 27
- 108030003182 L-allo-threonine aldolases Proteins 0.000 claims abstract description 19
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 68
- 102000004190 Enzymes Human genes 0.000 claims description 64
- 108090000790 Enzymes Proteins 0.000 claims description 64
- 239000004473 Threonine Substances 0.000 claims description 56
- 229960002898 threonine Drugs 0.000 claims description 56
- 238000000034 method Methods 0.000 claims description 52
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims description 48
- 230000000694 effects Effects 0.000 claims description 45
- 239000004471 Glycine Substances 0.000 claims description 34
- AYFVYJQAPQTCCC-STHAYSLISA-N D-threonine Chemical compound C[C@H](O)[C@@H](N)C(O)=O AYFVYJQAPQTCCC-STHAYSLISA-N 0.000 claims description 17
- 241000589516 Pseudomonas Species 0.000 claims description 14
- 229930182822 D-threonine Natural products 0.000 claims description 13
- 241000186063 Arthrobacter Species 0.000 claims description 12
- AYFVYJQAPQTCCC-PWNYCUMCSA-N D-Allothreonine Chemical compound C[C@@H](O)[C@@H](N)C(O)=O AYFVYJQAPQTCCC-PWNYCUMCSA-N 0.000 claims description 9
- AYFVYJQAPQTCCC-HRFVKAFMSA-N L-allothreonine Chemical compound C[C@H](O)[C@H](N)C(O)=O AYFVYJQAPQTCCC-HRFVKAFMSA-N 0.000 claims description 7
- 241000193830 Bacillus <bacterium> Species 0.000 claims description 6
- 244000005700 microbiome Species 0.000 claims description 4
- 241000588986 Alcaligenes Species 0.000 claims 1
- 239000000243 solution Substances 0.000 description 50
- 229960002449 glycine Drugs 0.000 description 32
- 235000008521 threonine Nutrition 0.000 description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
- 238000006243 chemical reaction Methods 0.000 description 20
- 239000013078 crystal Substances 0.000 description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- 238000002360 preparation method Methods 0.000 description 16
- 210000004027 cell Anatomy 0.000 description 14
- 108010068561 Fructose-Bisphosphate Aldolase Proteins 0.000 description 13
- 102000001390 Fructose-Bisphosphate Aldolase Human genes 0.000 description 13
- 238000006911 enzymatic reaction Methods 0.000 description 13
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 11
- 230000015572 biosynthetic process Effects 0.000 description 11
- 239000001963 growth medium Substances 0.000 description 11
- 230000008569 process Effects 0.000 description 11
- 238000003786 synthesis reaction Methods 0.000 description 11
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 230000002255 enzymatic effect Effects 0.000 description 9
- 239000007788 liquid Substances 0.000 description 9
- NGVDGCNFYWLIFO-UHFFFAOYSA-N pyridoxal 5'-phosphate Chemical compound CC1=NC=C(COP(O)(O)=O)C(C=O)=C1O NGVDGCNFYWLIFO-UHFFFAOYSA-N 0.000 description 9
- 235000007682 pyridoxal 5'-phosphate Nutrition 0.000 description 9
- 239000011589 pyridoxal 5'-phosphate Substances 0.000 description 9
- 239000002253 acid Substances 0.000 description 8
- 239000007864 aqueous solution Substances 0.000 description 8
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- 235000011114 ammonium hydroxide Nutrition 0.000 description 7
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- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 4
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- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 4
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- 229920002472 Starch Polymers 0.000 description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 4
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- 238000004458 analytical method Methods 0.000 description 4
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- 238000002955 isolation Methods 0.000 description 4
- 239000008363 phosphate buffer Substances 0.000 description 4
- 239000011591 potassium Substances 0.000 description 4
- 229910052700 potassium Inorganic materials 0.000 description 4
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 4
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- 238000005406 washing Methods 0.000 description 4
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 3
- 241000894006 Bacteria Species 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 229910002651 NO3 Inorganic materials 0.000 description 3
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 3
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 3
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- 235000011130 ammonium sulphate Nutrition 0.000 description 3
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- MUPFEKGTMRGPLJ-ZQSKZDJDSA-N raffinose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO[C@@H]2[C@@H]([C@@H](O)[C@@H](O)[C@@H](CO)O2)O)O1 MUPFEKGTMRGPLJ-ZQSKZDJDSA-N 0.000 description 1
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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
- C12P13/08—Lysine; Diaminopimelic acid; Threonine; Valine
-
- 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
- C12N9/88—Lyases (4.)
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)
- Enzymes And Modification Thereof (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP20998481A JPS58116691A (ja) | 1981-12-28 | 1981-12-28 | Ｌ−スレオニンの取得方法 |
| JP20998581A JPS58116692A (ja) | 1981-12-28 | 1981-12-28 | スレオニン混合物からのｌ−スレオニン取得方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2518988A1 true FR2518988A1 (fr) | 1983-07-01 |
| FR2518988B1 FR2518988B1 (enExample) | 1985-03-22 |
Family
ID=26517791
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8221816A Granted FR2518988A1 (fr) | 1981-12-28 | 1982-12-27 | Procede pour preparer la l-threonine |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US4492757A (enExample) |
| DE (1) | DE3247703C2 (enExample) |
| FR (1) | FR2518988A1 (enExample) |
| GB (1) | GB2113691B (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0507153A3 (en) * | 1991-03-27 | 1993-12-15 | Celgene Corp | Stereoisomeric enrichment of 2-amino-3-hydroxy-3-phenyl-propionic acids |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PT552041E (pt) * | 1992-01-15 | 2000-12-29 | Squibb & Sons Inc | Processo enzimaticos para a resolucao de misturas enantiomericas de compostos uteis como intermediarios para a preparacao de taxanos |
| TW397866B (en) * | 1993-07-14 | 2000-07-11 | Bristol Myers Squibb Co | Enzymatic processes for the resolution of enantiomeric mixtures of compounds useful as intermediates in the preparation of taxanes |
| US5860770A (en) * | 1997-06-10 | 1999-01-19 | A Creative Research & Testing Co. | Method of soil erosion control |
| EP1451168A4 (en) * | 2001-11-30 | 2005-08-24 | Bristol Myers Squibb Co | PACLITAXELSOLVATE |
| CN101838214A (zh) * | 2010-05-30 | 2010-09-22 | 中国科学院亚热带农业生态研究所 | 一种饲料添加剂dl-苏氨酸螯合铜的制备方法 |
| CN112387299B (zh) * | 2020-11-30 | 2022-02-01 | 江南大学 | 一种生物质化学-酶法制备l-呋喃丝氨酸的方法 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3600279A (en) * | 1970-06-01 | 1971-08-17 | Takeda Chemical Industries Ltd | Method for producing d-pantoic acid |
| DE2558158A1 (de) * | 1974-12-26 | 1976-07-01 | Tanabe Seiyaku Co | Neues verfahren zur herstellung von threo-threonin |
| JPS56121491A (en) * | 1980-02-25 | 1981-09-24 | Denki Kagaku Kogyo Kk | Preparation of l-threonine |
-
1982
- 1982-12-13 US US06/449,216 patent/US4492757A/en not_active Expired - Fee Related
- 1982-12-23 DE DE3247703A patent/DE3247703C2/de not_active Expired
- 1982-12-23 GB GB08236625A patent/GB2113691B/en not_active Expired
- 1982-12-27 FR FR8221816A patent/FR2518988A1/fr active Granted
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3600279A (en) * | 1970-06-01 | 1971-08-17 | Takeda Chemical Industries Ltd | Method for producing d-pantoic acid |
| DE2558158A1 (de) * | 1974-12-26 | 1976-07-01 | Tanabe Seiyaku Co | Neues verfahren zur herstellung von threo-threonin |
| JPS56121491A (en) * | 1980-02-25 | 1981-09-24 | Denki Kagaku Kogyo Kk | Preparation of l-threonine |
Non-Patent Citations (1)
| Title |
|---|
| Patent Abstracts of Japan Vol. 5, no. 200, 18 décembre 1981 & JP-A-56-121491 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0507153A3 (en) * | 1991-03-27 | 1993-12-15 | Celgene Corp | Stereoisomeric enrichment of 2-amino-3-hydroxy-3-phenyl-propionic acids |
Also Published As
| Publication number | Publication date |
|---|---|
| GB2113691A (en) | 1983-08-10 |
| DE3247703A1 (de) | 1983-07-14 |
| FR2518988B1 (enExample) | 1985-03-22 |
| DE3247703C2 (de) | 1984-11-22 |
| US4492757A (en) | 1985-01-08 |
| GB2113691B (en) | 1985-03-06 |
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