DK0874801T3 - Process for Extracting Optically Active L-Alpha-Amino-Carboxylic Acids from the Corresponding Racemic D, L-Alpha-Amino-Carboxylic Acids - Google Patents

Process for Extracting Optically Active L-Alpha-Amino-Carboxylic Acids from the Corresponding Racemic D, L-Alpha-Amino-Carboxylic Acids

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Publication number
DK0874801T3
DK0874801T3 DK96943040T DK96943040T DK0874801T3 DK 0874801 T3 DK0874801 T3 DK 0874801T3 DK 96943040 T DK96943040 T DK 96943040T DK 96943040 T DK96943040 T DK 96943040T DK 0874801 T3 DK0874801 T3 DK 0874801T3
Authority
DK
Denmark
Prior art keywords
alpha
aminocarboxylic
acetyl
acid
aminocarboxylic acids
Prior art date
Application number
DK96943040T
Other languages
Danish (da)
Inventor
Karlheinz Drauz
Andreas Bommarius
Michael Karrenbauer
Guenter Knaup
Original Assignee
Degussa
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
Application filed by Degussa filed Critical Degussa
Application granted granted Critical
Publication of DK0874801T3 publication Critical patent/DK0874801T3/en

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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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C227/30—Preparation of optical isomers
    • C07C227/34—Preparation of optical isomers by separation of optical isomers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C227/36—Racemisation of optical isomers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
    • C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
    • C07C319/20—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides by reactions not involving the formation of sulfide groups
    • 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
    • C12P41/00—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture
    • C12P41/006—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture by reactions involving C-N bonds, e.g. nitriles, amides, hydantoins, carbamates, lactames, transamination reactions, or keto group formation from racemic mixtures
    • C12P41/007—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture by reactions involving C-N bonds, e.g. nitriles, amides, hydantoins, carbamates, lactames, transamination reactions, or keto group formation from racemic mixtures by reactions involving acyl derivatives of racemic amines

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Zoology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Wood Science & Technology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Microbiology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Biotechnology (AREA)
  • Analytical Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Biochemistry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)

Abstract

The disclosure relates to a process for obtaining optically active L- alpha -aminocarboxylic acids from the corresponding racemic D,L, alpha -aminocarboxylic acids. The following steps are involved: (a) the D,L, alpha -aminocarboxylic acids are acetylated; (b) the N-acetyl-L- alpha -aminocarboxylic acid present in the mixture of N-acetyl-D,L, alpha -aminocarboxylic acids thus obtained is broken down enzymatically into the L- alpha -aminocarboxylic acid; (c) the L- alpha -aminocarboxylic acid is separated from the mixture, a quantity of a solution with N-acetyl-D(L)- alpha -aminocarboxylic acids and a quantity of acetate equivalent to the L- alpha -aminocarboxylic acid being retained; and (d) the N-acetyl-D(L)- alpha -aminocarboxylic acid is racemised and recycled for enzymatic breakdown. Known extraction processes involving steps (a) to (d) have the disadvantage of producing large quantities of salts. Specifically, the processes are far removed from the ideal equation, according to which one hundred percent of the acetic anhydride and the D,L, alpha -aminocarboxylic acids are converted to L- alpha -aminocarboxylic acids and acetic acid. Adjusting the retained solution from step (c) in such a way as to obtain a solution consisting essentially of N-acetyl-D-(L)- alpha -aminocarboxylic acid salt and free acetic acid in equilibrium with acetate and free N-acetyl-D(L)- alpha -aminocarboxylic acid and from which acetic acid is extracted by distillation makes it surprisingly easy to feed the solution formed as "mother liquor" following separation of the L- alpha -aminocarboxylic acids in the circuit and to achieve a materials balance as close as possible to the ideal.
DK96943040T 1995-12-13 1996-12-05 Process for Extracting Optically Active L-Alpha-Amino-Carboxylic Acids from the Corresponding Racemic D, L-Alpha-Amino-Carboxylic Acids DK0874801T3 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19546532A DE19546532C2 (en) 1995-12-13 1995-12-13 Process for obtaining optically active L-alpha-aminocarboxylic acids from corresponding racemic D, L-alpha-aminocarboxylic acids
PCT/EP1996/005440 WO1997021663A1 (en) 1995-12-13 1996-12-05 Process for obtaining optically active l-alpha-aminocarboxylic acids from corresponding racemic d,l-alpha-aminocarboxylic acids

Publications (1)

Publication Number Publication Date
DK0874801T3 true DK0874801T3 (en) 2001-07-23

Family

ID=7780007

Family Applications (1)

Application Number Title Priority Date Filing Date
DK96943040T DK0874801T3 (en) 1995-12-13 1996-12-05 Process for Extracting Optically Active L-Alpha-Amino-Carboxylic Acids from the Corresponding Racemic D, L-Alpha-Amino-Carboxylic Acids

Country Status (9)

Country Link
EP (1) EP0874801B1 (en)
JP (1) JP3639599B2 (en)
AT (1) ATE202074T1 (en)
AU (1) AU1190897A (en)
DE (2) DE19546532C2 (en)
DK (1) DK0874801T3 (en)
ES (1) ES2159773T3 (en)
PT (1) PT874801E (en)
WO (1) WO1997021663A1 (en)

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5037277B2 (en) * 1972-08-31 1975-12-01
JPS5233194B2 (en) * 1973-04-24 1977-08-26
DE3435095C2 (en) * 1984-09-25 1986-07-24 Degussa Ag, 6000 Frankfurt Process for the racemization of N-acetyl-D (L) -α-amino carboxylic acids
DE3438189A1 (en) * 1984-10-18 1986-04-24 Hoechst Ag, 6230 Frankfurt METHOD FOR PRODUCING AROMATICALLY SUBSTITUTED L-AMINO ACIDS
DE3603986A1 (en) * 1986-02-08 1987-08-13 Degussa METHOD FOR PROCESSING THE SOLUTION REMAINING FROM THE ENZYMATIC RACEMAT CLEAVING OF AN N-ACETYL-DL-AMINOCARBONIC ACID IN THE PRESENCE OF A L-AMINO ACID ACYLASE
DE3702689A1 (en) * 1987-01-30 1988-08-11 Degussa METHOD FOR ISOLATING L-AMINO ACIDS
SU1685924A1 (en) * 1988-03-22 1991-10-23 Армянский филиал Всесоюзного научно-исследовательского института химических реактивов и особо чистых химических веществ Method for obtaining optically active l-aminoacids

Also Published As

Publication number Publication date
JP3639599B2 (en) 2005-04-20
PT874801E (en) 2001-10-30
EP0874801B1 (en) 2001-06-13
DE19546532A1 (en) 1997-06-19
ES2159773T3 (en) 2001-10-16
EP0874801A1 (en) 1998-11-04
DE19546532C2 (en) 2000-04-20
AU1190897A (en) 1997-07-03
WO1997021663A1 (en) 1997-06-19
ATE202074T1 (en) 2001-06-15
JP2000501938A (en) 2000-02-22
DE59607102D1 (en) 2001-07-19

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