SE8306714L - PROCEDURE FOR MANUFACTURING L-CARNITIN AND CHEMICAL INTERMEDIATES USED - Google Patents
PROCEDURE FOR MANUFACTURING L-CARNITIN AND CHEMICAL INTERMEDIATES USEDInfo
- Publication number
- SE8306714L SE8306714L SE8306714A SE8306714A SE8306714L SE 8306714 L SE8306714 L SE 8306714L SE 8306714 A SE8306714 A SE 8306714A SE 8306714 A SE8306714 A SE 8306714A SE 8306714 L SE8306714 L SE 8306714L
- Authority
- SE
- Sweden
- Prior art keywords
- hydroxybutyrate
- converting
- carnitine
- salt
- chemical intermediates
- Prior art date
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 abstract 4
- 238000000034 method Methods 0.000 title abstract 3
- 239000000543 intermediate Substances 0.000 title abstract 2
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- 239000000126 substance Substances 0.000 title abstract 2
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 abstract 3
- WGNSGQNASYNCBU-GSVOUGTGSA-N (3r)-4-bromo-3-hydroxybutanoic acid Chemical compound BrC[C@H](O)CC(O)=O WGNSGQNASYNCBU-GSVOUGTGSA-N 0.000 abstract 2
- AKDAXGMVRMXFOO-GSVOUGTGSA-N (3r)-4-chloro-3-hydroxybutanoic acid Chemical compound ClC[C@H](O)CC(O)=O AKDAXGMVRMXFOO-GSVOUGTGSA-N 0.000 abstract 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 abstract 1
- 101710088194 Dehydrogenase Proteins 0.000 abstract 1
- WDJHALXBUFZDSR-UHFFFAOYSA-N acetoacetic acid Chemical class CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 abstract 1
- 150000001408 amides Chemical class 0.000 abstract 1
- 230000002255 enzymatic effect Effects 0.000 abstract 1
- 244000005700 microbiome Species 0.000 abstract 1
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Inorganic materials [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 abstract 1
- 235000009518 sodium iodide Nutrition 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
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/24—Preparation of oxygen-containing organic compounds containing a carbonyl group
- C12P7/26—Ketones
-
- 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
- C12N9/0004—Oxidoreductases (1.)
- C12N9/0006—Oxidoreductases (1.) acting on CH-OH groups as donors (1.1)
-
- 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
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/40—Preparation of oxygen-containing organic compounds containing a carboxyl group including Peroxycarboxylic acids
- C12P7/42—Hydroxy-carboxylic acids
-
- 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
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/62—Carboxylic acid esters
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Health & Medical Sciences (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)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
A process for preparing L- carnitine which comprises exposing gamma - substituted acetoacetic acid esters or amides to the fermentative enzymatic action of a microorganism which elaborates L- beta -hydroxyacyl CoA dehydrogenase [EC1.1.1.35], recovering the resulting, optically active, corresponding gamma -substituted- beta - hydroxybutyric acid derivative and converting said derivative to L- carnitine. An improvement in the process is also disclosed which comprises reacting a 4-chloro-3(R)- hydroxybutyrate with sodium iodide or bromide to produce the corresponding 4-iodo- or 4-bromo-3(R)- hydroxybutyrate, converting the 4- iodo or 4-bromo-3(R)-hydroxybutyrate to the trimethylamino-3(R)- hydroxybutyrate salt, then converting the trimethylamino-3(R)- hydroxybutyrate salt into L-carnitine inner salt. Novel chemical intermediates prepared in the processes are also disclosed; namely the 3(R) forms of <IMAGE> where R represents specified esterifying or amidifying groups and X is Cl, Br, I or OH.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/447,171 US4642290A (en) | 1982-12-06 | 1982-12-06 | Process for preparing a compound for use in the production of L-carnitine |
| US54495783A | 1983-10-24 | 1983-10-24 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| SE8306714D0 SE8306714D0 (en) | 1983-12-05 |
| SE8306714L true SE8306714L (en) | 1984-06-07 |
| SE455501B SE455501B (en) | 1988-07-18 |
Family
ID=27034888
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE8306714A SE455501B (en) | 1982-12-06 | 1983-12-05 | OPTICALLY ACTIVE GAMMA-SUBSTITUTED BETA-HYDROXISMORIC ACID DERIVATIVES AND PROCEDURES FOR THE PRODUCTION OF THESE BY FERMENTATIVE ENZYMATIC EFFECT OF A MICRO-ORGANIS |
Country Status (23)
| Country | Link |
|---|---|
| JP (1) | JPH0767674A (en) |
| KR (1) | KR840008165A (en) |
| AT (1) | AT393136B (en) |
| AU (1) | AU566906B2 (en) |
| CA (1) | CA1225956A (en) |
| CH (1) | CH661498A5 (en) |
| DE (1) | DE3344085C2 (en) |
| DK (1) | DK163917C (en) |
| ES (1) | ES8601305A1 (en) |
| FI (1) | FI81115C (en) |
| FR (1) | FR2537130B1 (en) |
| GB (1) | GB2132614B (en) |
| GR (1) | GR78767B (en) |
| IE (1) | IE56322B1 (en) |
| IL (1) | IL70352A (en) |
| IT (1) | IT1167289B (en) |
| LU (1) | LU85115A1 (en) |
| NL (1) | NL8304190A (en) |
| NO (1) | NO159291C (en) |
| PH (1) | PH20456A (en) |
| PT (1) | PT77780B (en) |
| SE (1) | SE455501B (en) |
| TR (1) | TR23136A (en) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK544284A (en) * | 1983-12-06 | 1985-06-07 | Hoffmann La Roche | PROCEDURE FOR THE PREPARATION OF OPTIC ACTIVE PROPIONIC ACID DERIVATIVES |
| IT1181908B (en) * | 1984-07-12 | 1987-09-30 | Debi Derivati Biologici | PROCEDURE FOR THE PREPARATION OF L-CARNITINA |
| IT1181812B (en) * | 1984-07-27 | 1987-09-30 | Sigma Tau Ind Farmaceuti | PROCEDURE FOR THE PREPARATION OF THE GAMMA-DIMETHYLAMINE L-BETA-HYDROXYBUTIRRIC ACID |
| IT1190358B (en) * | 1985-05-24 | 1988-02-16 | Sclavo Spa | PROCEDURE FOR THE PREPARATION OF L-CARNITINA |
| JPS62126997A (en) * | 1985-11-28 | 1987-06-09 | Nippon Synthetic Chem Ind Co Ltd:The | Method for producing optically active γ-halo-β hydroxybutyric acid ester |
| IT1189070B (en) * | 1986-03-14 | 1988-01-28 | Donegani Guido Ist | PROCESS FOR THE PREPARATION OF THE L (-) - CARNITINE CHLORIDE FROM FOREIGN 3,4-EPOXYBUTYRRICS |
| JPH0678277B2 (en) * | 1988-02-19 | 1994-10-05 | 高砂香料工業株式会社 | Process for producing optically active alcohol and its derivative |
| JP2939646B2 (en) * | 1990-07-17 | 1999-08-25 | チッソ株式会社 | 4-Substituted-2-hydroxybutanoic acid esters and production method |
| US5215919A (en) * | 1991-02-25 | 1993-06-01 | Takeda Chemical Industries, Ltd. | Process for producing optically active 2-hydroxycycloalkanecarboxylic acid esters using microbially derived reductase |
| US5324662A (en) | 1992-05-15 | 1994-06-28 | E. R. Squibb & Sons, Inc. | Stereoselective microbial or enzymatic reduction of 3,5-dioxo esters to 3-hydroxy-5-oxo, 3-oxo-5-hydroxy, and 3,5-dihydroxy esters |
| JP3155107B2 (en) * | 1993-01-12 | 2001-04-09 | ダイセル化学工業株式会社 | Method for producing optically active 4-halo-3-hydroxybutyrate |
| JP2000189170A (en) * | 1998-05-08 | 2000-07-11 | Daicel Chem Ind Ltd | Method for producing optically active 4-halo-3-hydroxybutyrate |
| CN1162422C (en) | 1998-08-05 | 2004-08-18 | 钟渊化学工业株式会社 | Process for preparing optically active 2-[6-(hydroxymethyl)-1,3-dioxan-4-yl]acetic acid derivatives |
| JP4578240B2 (en) * | 2002-08-09 | 2010-11-10 | コデクシス， インコーポレイテッド | Enzymatic process for the production of 4-substituted 3-hydroxybutyric acid derivatives |
| DE10315760A1 (en) * | 2003-04-07 | 2004-10-21 | Basf Ag | L-carnitine dehydrogenases, their derivatives and a process for the preparation of substituted (S) -alkanols |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3931410A (en) * | 1974-02-28 | 1976-01-06 | The Upjohn Company | Composition and method of use |
| CH589604A5 (en) * | 1974-04-26 | 1977-07-15 | Lonza Ag | |
| JPS5139634A (en) * | 1974-09-27 | 1976-04-02 | Ono Pharmaceutical Co | Ganma amino beeta hidorokishibutansananirido no seizoho |
| JPS6017776B2 (en) * | 1979-11-07 | 1985-05-07 | 電気化学工業株式会社 | Production method of γ-chloro-β-hydroxybutyric acid alkyl ester |
| JPS5950661B2 (en) * | 1980-07-28 | 1984-12-10 | 電気化学工業株式会社 | Method for producing γ-amino-β-hydroxybutyric acid |
| JPS5950663B2 (en) * | 1981-04-28 | 1984-12-10 | 電気化学工業株式会社 | Method for producing γ-amino-β-hydroxybutyric acid |
-
1983
- 1983-11-22 IE IE2732/83A patent/IE56322B1/en not_active IP Right Cessation
- 1983-11-28 AU AU21758/83A patent/AU566906B2/en not_active Ceased
- 1983-11-29 CA CA000442170A patent/CA1225956A/en not_active Expired
- 1983-11-30 IL IL8370352A patent/IL70352A/en not_active IP Right Cessation
- 1983-12-01 GR GR73128A patent/GR78767B/el unknown
- 1983-12-02 FI FI834419A patent/FI81115C/en not_active IP Right Cessation
- 1983-12-02 CH CH6448/83A patent/CH661498A5/en not_active IP Right Cessation
- 1983-12-05 AT AT4237/83A patent/AT393136B/en not_active IP Right Cessation
- 1983-12-05 SE SE8306714A patent/SE455501B/en not_active IP Right Cessation
- 1983-12-05 NO NO834461A patent/NO159291C/en unknown
- 1983-12-05 DK DK559283A patent/DK163917C/en not_active IP Right Cessation
- 1983-12-05 GB GB08332359A patent/GB2132614B/en not_active Expired
- 1983-12-05 PH PH29928A patent/PH20456A/en unknown
- 1983-12-05 LU LU85115A patent/LU85115A1/en unknown
- 1983-12-05 IT IT8324018A patent/IT1167289B/en active
- 1983-12-05 ES ES83527807A patent/ES8601305A1/en not_active Expired
- 1983-12-06 FR FR8319505A patent/FR2537130B1/en not_active Expired
- 1983-12-06 DE DE3344085A patent/DE3344085C2/en not_active Expired - Fee Related
- 1983-12-06 PT PT77780A patent/PT77780B/en not_active IP Right Cessation
- 1983-12-06 NL NL8304190A patent/NL8304190A/en not_active Application Discontinuation
- 1983-12-06 TR TR10354/83A patent/TR23136A/en unknown
- 1983-12-06 KR KR1019830005765A patent/KR840008165A/en not_active Ceased
-
1993
- 1993-09-01 JP JP21771093A patent/JPH0767674A/en active Pending
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