DE240423T1 - Verfahren zur herstellung von l-carnitin. - Google Patents
Verfahren zur herstellung von l-carnitin.Info
- Publication number
- DE240423T1 DE240423T1 DE198787400693T DE87400693T DE240423T1 DE 240423 T1 DE240423 T1 DE 240423T1 DE 198787400693 T DE198787400693 T DE 198787400693T DE 87400693 T DE87400693 T DE 87400693T DE 240423 T1 DE240423 T1 DE 240423T1
- Authority
- DE
- Germany
- Prior art keywords
- dehydrocarnitine
- solution
- process according
- carnitine
- reaction medium
- 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.)
- Pending
Links
- PHIQHXFUZVPYII-ZCFIWIBFSA-N (R)-carnitine Chemical compound C[N+](C)(C)C[C@H](O)CC([O-])=O PHIQHXFUZVPYII-ZCFIWIBFSA-N 0.000 title claims 4
- 238000004519 manufacturing process Methods 0.000 title 1
- 238000000034 method Methods 0.000 claims abstract 12
- YNOWULSFLVIUDH-UHFFFAOYSA-N 3-dehydrocarnitine Chemical compound C[N+](C)(C)CC(=O)CC([O-])=O YNOWULSFLVIUDH-UHFFFAOYSA-N 0.000 claims 7
- 239000000243 solution Substances 0.000 claims 7
- 239000012429 reaction media Substances 0.000 claims 5
- 108010029922 carnitine dehydrogenase Proteins 0.000 claims 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 2
- 108090000790 Enzymes Proteins 0.000 claims 2
- 102000004190 Enzymes Human genes 0.000 claims 2
- 108090000698 Formate Dehydrogenases Proteins 0.000 claims 2
- BAWFJGJZGIEFAR-NNYOXOHSSA-N NAD zwitterion Chemical compound NC(=O)C1=CC=C[N+]([C@H]2[C@@H]([C@H](O)[C@@H](COP([O-])(=O)OP(O)(=O)OC[C@@H]3[C@H]([C@@H](O)[C@@H](O3)N3C4=NC=NC(N)=C4N=C3)O)O2)O)=C1 BAWFJGJZGIEFAR-NNYOXOHSSA-N 0.000 claims 2
- 239000007864 aqueous solution Substances 0.000 claims 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims 2
- 229950006238 nadide Drugs 0.000 claims 2
- 229930027945 nicotinamide-adenine dinucleotide Natural products 0.000 claims 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 1
- 229910021529 ammonia Inorganic materials 0.000 claims 1
- VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 claims 1
- 230000002255 enzymatic effect Effects 0.000 claims 1
- 235000019253 formic acid Nutrition 0.000 claims 1
- BOPGDPNILDQYTO-NNYOXOHSSA-N nicotinamide-adenine dinucleotide Chemical compound C1=CCC(C(=O)N)=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OC[C@@H]2[C@H]([C@@H](O)[C@@H](O2)N2C3=NC=NC(N)=C3N=C2)O)O1 BOPGDPNILDQYTO-NNYOXOHSSA-N 0.000 claims 1
- PHIQHXFUZVPYII-ZCFIWIBFSA-O (R)-carnitinium Chemical compound C[N+](C)(C)C[C@H](O)CC(O)=O PHIQHXFUZVPYII-ZCFIWIBFSA-O 0.000 abstract 3
- 229960004203 carnitine Drugs 0.000 abstract 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- 239000012736 aqueous medium Substances 0.000 abstract 1
- 229910052500 inorganic mineral Inorganic materials 0.000 abstract 1
- 239000002609 medium Substances 0.000 abstract 1
- 239000011707 mineral Substances 0.000 abstract 1
- 102000004169 proteins and genes Human genes 0.000 abstract 1
- 108090000623 proteins and genes Proteins 0.000 abstract 1
- 238000000746 purification Methods 0.000 abstract 1
- 238000000926 separation method Methods 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 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
- C12P13/007—Carnitine; Butyrobetaine; Crotonobetaine
-
- 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
- C12P1/00—Preparation of compounds or compositions, not provided for in groups C12P3/00 - C12P39/00, by using microorganisms or enzymes
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Genetics & Genomics (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Microbiology (AREA)
- Mycology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Detergent Compositions (AREA)
- Washing And Drying Of Tableware (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pyrane Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
Claims (8)
1. Verfahren zur Herstellung von L-Carnitin durch Reduktion von Dehydrocarnitin mittels Nicotinamid-adenin-dinucleotid
(NADH) in Gegenwart von Carnitin-dehydrogenase (CDH), wobei das gebildete NAD+ mit einem Formiat unter Einwirkung von
Formiat-dehydrogenase (FDH) reduziert wird, dadurch gekennzeichnet, dass die das Reaktionsmedium darstellende
wässerige Lösung im Verlauf der Biokonversion eine Ionen-
° stärke von mindestens 0,5 m aufweist.
2. Verfahren nach Anspruch 1, dadurch gekennzeichnet, dass die Ionenstärke des Reaktionsmediums zumindest am Schluss des
Vorgangs 0,6 bis 3 m beträgt.
3. Verfahren nach Anspruch 1, bei dem eine wässerige Lösung von Dehydrocarnitin nach und nach in eine Lösung der Enzyme
gegossen wird, dadurch gekennzeichnet, dass das Reaktionsmedium zu Beginn des Vorgangs eine Ionenstärke von 0,1 bis
0,4 m und am Ende des Vorgangs von 0,8 bis 2,5 m aufweist.
4. Verfahren nach einem der Ansprüche 1 bis 3, dadurch gekennzeichnet,
dass die Ionenstärke vorwiegend durch Ammoniumformiat bereitgestellt wird.
5. Verfahren nach einem der Ansprüche 1 bis 4, bei dem das
Dehydrocarnitin in Form des Hydrochlorids eingesetzt wird und das Reaktionsmedium mit Ammoniak neutralisiert wird,
dadurch gekennzeichnet, dass eine Ameisensäurelösung gleichzeitig mit der Dehydrocarnitinlösung in das Medium
gegossen wird.
20
25
30
35
-2-
6. Verfahren nach einem der vorstehenden Ansprüche, dadurch gekennzeichnet, dass das Reaktionsmedium 200 bis 1000 Einheiten
des Enzyms CDH pro Mol an insgesamt verwendetem Dehydrocarnitin enthält.
7. Verfahren nach einem der vorstehenden Ansprüche, dadurch gekennzeichnet, dass die Dehydrocarnitinlösung eine Konzentration
von 0,2 bis 2 m aufweist.
8. Verfahren nach Anspruch 7, dadurch gekennzeichnet, dass
diese Lösung in eine Lösung der Enzyme mit einer solchen Geschwindigkeit gegossen wird, dass das Dehydrocarnitin in
dem Masse, wie es in die enzymatische Lösung gelangt, in L-Carnitin
übergeführt wird.
15
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR868604832A FR2596756B1 (fr) | 1986-04-04 | 1986-04-04 | Procede de purification de la carnitine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE240423T1 true DE240423T1 (de) | 1988-02-04 |
Family
ID=9333890
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE8787400692T Expired - Fee Related DE3764511D1 (de) | 1986-04-04 | 1987-03-27 | Verfahren zur reinigung von carnitin. |
| DE198787400692T Pending DE240422T1 (de) | 1986-04-04 | 1987-03-27 | Verfahren zur reinigung von carnitin. |
| DE198787400693T Pending DE240423T1 (de) | 1986-04-04 | 1987-03-27 | Verfahren zur herstellung von l-carnitin. |
Family Applications Before (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE8787400692T Expired - Fee Related DE3764511D1 (de) | 1986-04-04 | 1987-03-27 | Verfahren zur reinigung von carnitin. |
| DE198787400692T Pending DE240422T1 (de) | 1986-04-04 | 1987-03-27 | Verfahren zur reinigung von carnitin. |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US4751325A (de) |
| EP (2) | EP0240423A3 (de) |
| JP (2) | JPS62249956A (de) |
| AT (1) | ATE55982T1 (de) |
| CA (1) | CA1282428C (de) |
| DE (3) | DE3764511D1 (de) |
| DK (2) | DK172587A (de) |
| ES (2) | ES2000115A4 (de) |
| FR (1) | FR2596756B1 (de) |
| GR (2) | GR880300001T1 (de) |
| NO (2) | NO871359L (de) |
| PT (2) | PT84615B (de) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2621325B1 (fr) * | 1987-10-02 | 1990-03-30 | Elf Aquitaine | Procede perfectionne de preparation de l-carnitine |
| FR2623520B1 (fr) * | 1987-11-23 | 1990-04-20 | Sanofi Sa | Procede enzymatique continu de preparation de la l-carnitine |
| JP3059735B2 (ja) * | 1989-10-13 | 2000-07-04 | 旭化成工業株式会社 | Ｌ―カルニチンデヒドロゲナーゼおよびその製造法 |
| JP2009102258A (ja) * | 2007-10-23 | 2009-05-14 | Mitsubishi Rayon Co Ltd | Ｌ−カルニチンの精製方法 |
| JP2010143857A (ja) * | 2008-12-18 | 2010-07-01 | Mitsubishi Rayon Co Ltd | カルニチンの精製方法 |
| TWI485126B (zh) * | 2009-11-18 | 2015-05-21 | Lonza Ag | 製造ｌ－肉鹼的方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2398046A1 (fr) * | 1977-07-18 | 1979-02-16 | Inst Francais Du Petrole | Synthese enzymatique de la l-carnitine |
| FR2526442B1 (fr) * | 1982-05-06 | 1985-09-27 | Inst Francais Du Petrole | Production de glucose deshydrogenase et utilisation de l'enzyme obtenu dans la synthese enzymatique de la l-carnitine |
| DE3463261D1 (en) * | 1983-12-28 | 1987-05-27 | Sigma Tau Ind Farmaceuti | Salts of l-carnitine and alkanoyl l-carnitines and process for preparing same |
-
1986
- 1986-04-04 FR FR868604832A patent/FR2596756B1/fr not_active Expired
-
1987
- 1987-03-27 ES ES87400693T patent/ES2000115A4/es active Pending
- 1987-03-27 DE DE8787400692T patent/DE3764511D1/de not_active Expired - Fee Related
- 1987-03-27 DE DE198787400692T patent/DE240422T1/de active Pending
- 1987-03-27 ES ES87400692T patent/ES2000114A4/es active Pending
- 1987-03-27 EP EP87400693A patent/EP0240423A3/de not_active Withdrawn
- 1987-03-27 DE DE198787400693T patent/DE240423T1/de active Pending
- 1987-03-27 AT AT87400692T patent/ATE55982T1/de active
- 1987-03-27 EP EP87400692A patent/EP0240422B1/de not_active Expired - Lifetime
- 1987-04-01 NO NO871359A patent/NO871359L/no unknown
- 1987-04-01 NO NO871360A patent/NO167024C/no unknown
- 1987-04-02 JP JP62079856A patent/JPS62249956A/ja active Pending
- 1987-04-02 PT PT84615A patent/PT84615B/pt not_active IP Right Cessation
- 1987-04-02 JP JP62079857A patent/JPS62253388A/ja active Pending
- 1987-04-02 US US07/034,387 patent/US4751325A/en not_active Expired - Fee Related
- 1987-04-02 PT PT84616A patent/PT84616B/pt not_active IP Right Cessation
- 1987-04-03 DK DK172587A patent/DK172587A/da active IP Right Grant
- 1987-04-03 DK DK172487A patent/DK172487A/da active IP Right Grant
- 1987-04-03 CA CA000533863A patent/CA1282428C/fr not_active Expired - Fee Related
-
1988
- 1988-05-20 GR GR88300001T patent/GR880300001T1/el unknown
- 1988-05-20 GR GR88300002T patent/GR880300002T1/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DK172487A (da) | 1987-10-05 |
| FR2596756A1 (fr) | 1987-10-09 |
| NO871360D0 (no) | 1987-04-01 |
| FR2596756B1 (fr) | 1988-07-22 |
| CA1282428C (fr) | 1991-04-02 |
| EP0240422A2 (de) | 1987-10-07 |
| NO871359L (no) | 1987-10-05 |
| DK172487D0 (da) | 1987-04-03 |
| US4751325A (en) | 1988-06-14 |
| NO871359D0 (no) | 1987-04-01 |
| PT84615A (fr) | 1987-05-01 |
| DK172587D0 (da) | 1987-04-03 |
| GR880300002T1 (en) | 1988-10-18 |
| EP0240422B1 (de) | 1990-08-29 |
| PT84616B (pt) | 1989-11-30 |
| ES2000114A4 (es) | 1987-12-16 |
| NO167024B (no) | 1991-06-17 |
| GR880300001T1 (en) | 1988-10-18 |
| EP0240422A3 (en) | 1988-07-27 |
| DE3764511D1 (de) | 1990-10-04 |
| JPS62253388A (ja) | 1987-11-05 |
| DK172587A (da) | 1987-10-05 |
| NO871360L (no) | 1987-10-05 |
| NO167024C (no) | 1991-09-25 |
| EP0240423A2 (de) | 1987-10-07 |
| JPS62249956A (ja) | 1987-10-30 |
| DE240422T1 (de) | 1988-02-04 |
| ATE55982T1 (de) | 1990-09-15 |
| ES2000115A4 (es) | 1987-12-16 |
| PT84615B (pt) | 1989-11-30 |
| EP0240423A3 (de) | 1988-08-17 |
| PT84616A (fr) | 1987-05-01 |
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