ES8601305A1 - Process for preparing L- carnitine and chemical intermediates employed therein - Google Patents

Process for preparing L- carnitine and chemical intermediates employed therein

Info

Publication number
ES8601305A1
ES8601305A1 ES83527807A ES527807A ES8601305A1 ES 8601305 A1 ES8601305 A1 ES 8601305A1 ES 83527807 A ES83527807 A ES 83527807A ES 527807 A ES527807 A ES 527807A ES 8601305 A1 ES8601305 A1 ES 8601305A1
Authority
ES
Spain
Prior art keywords
hydroxybutyrate
carnitine
converting
preparing
salt
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
Application number
ES83527807A
Other languages
Spanish (es)
Other versions
ES527807A0 (en
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Sigma Tau Industrie Farmaceutiche Riunite SpA
Original Assignee
Sigma Tau Industrie Farmaceutiche Riunite SpA
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Priority claimed from US06/447,171 external-priority patent/US4642290A/en
Application filed by Sigma Tau Industrie Farmaceutiche Riunite SpA filed Critical Sigma Tau Industrie Farmaceutiche Riunite SpA
Publication of ES8601305A1 publication Critical patent/ES8601305A1/en
Publication of ES527807A0 publication Critical patent/ES527807A0/en
Granted legal-status Critical Current

Links

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)
  • 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)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Biomedical Technology (AREA)
  • Molecular Biology (AREA)
  • Medicinal Chemistry (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.
ES83527807A 1982-12-06 1983-12-05 A PROCEDURE FOR THE PREPARATION OF DERIVATIVES OF BETA-HYDROXYBUTYRIC ACID GAMMA-SUBSTITUTED Granted ES527807A0 (en)

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 (2)

Publication Number Publication Date
ES8601305A1 true ES8601305A1 (en) 1985-11-01
ES527807A0 ES527807A0 (en) 1985-11-01

Family

ID=27034888

Family Applications (1)

Application Number Title Priority Date Filing Date
ES83527807A Granted ES527807A0 (en) 1982-12-06 1983-12-05 A PROCEDURE FOR THE PREPARATION OF DERIVATIVES OF BETA-HYDROXYBUTYRIC ACID GAMMA-SUBSTITUTED

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) ES527807A0 (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)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0144832A3 (en) * 1983-12-06 1987-01-21 F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft Process for the preparation of optically active alpha-substituted 3-hydroxypropionic-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 Production of optically active gamma-halo-beta hydroxybutyric 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 Production of optically active 4-halo-3-hydroxybutyric acid ester
JP3803551B2 (en) 1998-08-05 2006-08-02 株式会社カネカ Process for producing optically active 2- [6- (hydroxymethyl) -1,3-dioxan-4-yl] acetic acid derivative
DE60336324D1 (en) * 2002-08-09 2011-04-21 Codexis Inc ENZYMATIC PROCEDURES FOR THE PREPARATION OF 4-SUBSTITUTED 3-HYDROXYBUTYLIC 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)

* Cited by examiner, † Cited by third party
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

Also Published As

Publication number Publication date
FR2537130A1 (en) 1984-06-08
GB8332359D0 (en) 1984-01-11
DE3344085C2 (en) 1993-10-14
GB2132614A (en) 1984-07-11
GB2132614B (en) 1986-03-26
IE832732L (en) 1984-06-06
IL70352A (en) 1987-10-20
JPH0767674A (en) 1995-03-14
IT1167289B (en) 1987-05-13
SE8306714D0 (en) 1983-12-05
NO159291C (en) 1988-12-14
FI834419A0 (en) 1983-12-02
IT8324018A0 (en) 1983-12-05
AU2175883A (en) 1984-06-14
IE56322B1 (en) 1991-06-19
PH20456A (en) 1987-01-14
FI834419A (en) 1984-06-07
SE455501B (en) 1988-07-18
DK559283A (en) 1984-06-07
DK163917C (en) 1992-09-14
FI81115B (en) 1990-05-31
AU566906B2 (en) 1987-11-05
SE8306714L (en) 1984-06-07
ATA423783A (en) 1991-01-15
PT77780A (en) 1984-01-01
NL8304190A (en) 1984-07-02
FI81115C (en) 1990-09-10
PT77780B (en) 1986-04-17
NO834461L (en) 1984-06-07
IL70352A0 (en) 1984-02-29
DK163917B (en) 1992-04-21
GR78767B (en) 1984-10-02
AT393136B (en) 1991-08-26
DE3344085A1 (en) 1984-06-07
FR2537130B1 (en) 1988-10-14
ES527807A0 (en) 1985-11-01
TR23136A (en) 1989-04-11
LU85115A1 (en) 1984-04-02
KR840008165A (en) 1984-12-13
DK559283D0 (en) 1983-12-05
CH661498A5 (en) 1987-07-31
CA1225956A (en) 1987-08-25
NO159291B (en) 1988-09-05

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Legal Events

Date Code Title Description
FD1A Patent lapsed

Effective date: 19970519