WO2003044206A3 - Process for the preparation of an enantiomerically enriched a-amino acid - Google Patents

Process for the preparation of an enantiomerically enriched a-amino acid Download PDF

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Publication number
WO2003044206A3
WO2003044206A3 PCT/NL2002/000758 NL0200758W WO03044206A3 WO 2003044206 A3 WO2003044206 A3 WO 2003044206A3 NL 0200758 W NL0200758 W NL 0200758W WO 03044206 A3 WO03044206 A3 WO 03044206A3
Authority
WO
WIPO (PCT)
Prior art keywords
amino acid
preparation
enantiomerically enriched
carbamoyl
carbamoylase
Prior art date
Application number
PCT/NL2002/000758
Other languages
French (fr)
Other versions
WO2003044206A2 (en
Inventor
Joannes Gerardus Theo Kierkels
Wilhelmus Hubertus Jos Boesten
Original Assignee
Dsm Ip Assets Bv
Joannes Gerardus Theo Kierkels
Boesten Wilhelmus H J
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 Dsm Ip Assets Bv, Joannes Gerardus Theo Kierkels, Boesten Wilhelmus H J filed Critical Dsm Ip Assets Bv
Priority to AU2002347652A priority Critical patent/AU2002347652A1/en
Priority to EP02783830A priority patent/EP1446492A2/en
Priority to JP2003545827A priority patent/JP2005509439A/en
Publication of WO2003044206A2 publication Critical patent/WO2003044206A2/en
Publication of WO2003044206A3 publication Critical patent/WO2003044206A3/en

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    • 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
    • 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
    • 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
    • C12P13/06—Alanine; Leucine; Isoleucine; Serine; Homoserine
    • 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
    • C12P13/12—Methionine; Cysteine; Cystine
    • 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
    • C12P13/22—Tryptophan; Tyrosine; Phenylalanine; 3,4-Dihydroxyphenylalanine
    • C12P13/222—Phenylalanine
    • 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
    • C12P41/009—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 hydantoins or carbamoylamino compounds

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

Abstract

The invention relates to a process for the preparation of an enantiomerically enriched D-α-amino acid in a reaction carried out in a one pot reaction in the presence of a hydantoinase and a D-carbamoylase, in which an N-carbamoyl-L-α-amino acid is converted into the corresponding D-α-amino acid and in which the N-carbamoyl-L-α-amino acid may be prepared from the corresponding L-α-amino acid. The enzymes used preferably originate from Agrobacterium radiobacter or Arthrobacter aurescens . Examples of very suitable α-amino acids are leucine, methionine, cysteine, threonine and phenylalanine.
PCT/NL2002/000758 2001-11-23 2002-11-22 Process for the preparation of an enantiomerically enriched a-amino acid WO2003044206A2 (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
AU2002347652A AU2002347652A1 (en) 2001-11-23 2002-11-22 Process for the preparation of an enantiomerically enriched a-amino acid
EP02783830A EP1446492A2 (en) 2001-11-23 2002-11-22 Process for the preparation of an enantiomerically enriched a-amino acid
JP2003545827A JP2005509439A (en) 2001-11-23 2002-11-22 Process for producing enantiomerically rich α-amino acids

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
NL1019416 2001-11-23
NL1019416A NL1019416C2 (en) 2001-11-23 2001-11-23 Process for preparing an enantiomerically enriched α-amino acid.

Publications (2)

Publication Number Publication Date
WO2003044206A2 WO2003044206A2 (en) 2003-05-30
WO2003044206A3 true WO2003044206A3 (en) 2003-12-18

Family

ID=19774336

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/NL2002/000758 WO2003044206A2 (en) 2001-11-23 2002-11-22 Process for the preparation of an enantiomerically enriched a-amino acid

Country Status (6)

Country Link
EP (1) EP1446492A2 (en)
JP (1) JP2005509439A (en)
CN (1) CN1592789A (en)
AU (1) AU2002347652A1 (en)
NL (1) NL1019416C2 (en)
WO (1) WO2003044206A2 (en)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1928103B (en) * 2006-08-30 2010-09-01 石家庄中天生物技术有限责任公司 Method of producing D-p-hydroxy-phenyl glycine by heterogeneous enzyme catalysis method
CN106676157A (en) * 2017-02-20 2017-05-17 南华大学 Application of legionella thalli in preparing amino acid profile transformation agent
CN110714035A (en) * 2019-11-15 2020-01-21 江南大学 Method for preparing D-aliphatic amino acid by cascade reaction

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0152977A1 (en) * 1984-02-02 1985-08-28 SCLAVO S.p.A. Process for the preparation of L-alpha-aminoacids
EP0625571A2 (en) * 1993-05-19 1994-11-23 Degussa Aktiengesellschaft Microorganisms, their use and method of production of L-alpha-amino acids
EP0745678A2 (en) * 1995-05-30 1996-12-04 Degussa Aktiengesellschaft Novel microorganism, its use and process for the preparation of L-alpha-aminoacids
EP0775748A2 (en) * 1995-11-23 1997-05-28 ENIRICERCHE S.p.A. Preparation of D-alpha-amino acids, using bacteria transformed with the carbamoylase-hydantoinase operon
WO2002061107A2 (en) * 2001-01-31 2002-08-08 Dsm Ip Assets B.V. Process for the preparation of enantiomer-enriched amino acids

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0152977A1 (en) * 1984-02-02 1985-08-28 SCLAVO S.p.A. Process for the preparation of L-alpha-aminoacids
EP0625571A2 (en) * 1993-05-19 1994-11-23 Degussa Aktiengesellschaft Microorganisms, their use and method of production of L-alpha-amino acids
EP0745678A2 (en) * 1995-05-30 1996-12-04 Degussa Aktiengesellschaft Novel microorganism, its use and process for the preparation of L-alpha-aminoacids
EP0775748A2 (en) * 1995-11-23 1997-05-28 ENIRICERCHE S.p.A. Preparation of D-alpha-amino acids, using bacteria transformed with the carbamoylase-hydantoinase operon
WO2002061107A2 (en) * 2001-01-31 2002-08-08 Dsm Ip Assets B.V. Process for the preparation of enantiomer-enriched amino acids

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
GROSS C ET AL: "PRODUCTION OF L-TRYPTOPHAN FROM D,L-5-INDOLYLMETHYLHYDANTOIN BY RESTING CELLS OF A MUTANT OF ARTHROBACTER SPECIES (DSM 3747)", JOURNAL OF BIOTECHNOLOGY, ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, NL, vol. 14, 1990, pages 363 - 375, XP000929684, ISSN: 0168-1656 *
RUNSER S ET AL: "D-P-HYDROXYPHENYLGLYCINE PRODUCTION FROM DL-5-P-HYDROXYPHENYLHYDANTOIN BY AGROBACTERIUM SP", APPLIED MICROBIOLOGY AND BIOTECHNOLOGY, SPRINGER VERLAG, BERLIN, DE, vol. 33, no. 4, 1990, pages 382 - 388, XP000951524, ISSN: 0175-7598 *

Also Published As

Publication number Publication date
EP1446492A2 (en) 2004-08-18
JP2005509439A (en) 2005-04-14
NL1019416C2 (en) 2003-06-02
CN1592789A (en) 2005-03-09
WO2003044206A2 (en) 2003-05-30
AU2002347652A1 (en) 2003-06-10
AU2002347652A8 (en) 2003-06-10

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