JPS5547630A - Optical resolution of phosphorus-containing amino acid - Google Patents

Optical resolution of phosphorus-containing amino acid

Info

Publication number
JPS5547630A
JPS5547630A JP12039078A JP12039078A JPS5547630A JP S5547630 A JPS5547630 A JP S5547630A JP 12039078 A JP12039078 A JP 12039078A JP 12039078 A JP12039078 A JP 12039078A JP S5547630 A JPS5547630 A JP S5547630A
Authority
JP
Japan
Prior art keywords
acyl
isomer
amino acid
containing amino
mpga
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.)
Granted
Application number
JP12039078A
Other languages
Japanese (ja)
Other versions
JPS6247520B2 (en
Inventor
Hitoshi Goi
Shinji Miyaji
Takashi Shomura
Akira Suzuki
Tomizo Niwa
Yujiro Yamada
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.)
Meiji Seika Kaisha Ltd
Original Assignee
Meiji Seika Kaisha Ltd
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 Meiji Seika Kaisha Ltd filed Critical Meiji Seika Kaisha Ltd
Priority to JP12039078A priority Critical patent/JPS5547630A/en
Priority to GB7933176A priority patent/GB2031896B/en
Priority to FR7925384A priority patent/FR2438054A1/en
Priority to DE2939269A priority patent/DE2939269C2/en
Publication of JPS5547630A publication Critical patent/JPS5547630A/en
Publication of JPS6247520B2 publication Critical patent/JPS6247520B2/ja
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
    • C12P13/00—Preparation of nitrogen-containing organic compounds
    • C12P13/04—Alpha- or beta- amino acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
    • C07F9/301—Acyclic saturated acids which can have further substituents on alkyl
    • 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
    • C12N9/14—Hydrolases (3)
    • C12N9/78—Hydrolases (3) acting on carbon to nitrogen bonds other than peptide bonds (3.5)
    • C12N9/80—Hydrolases (3) acting on carbon to nitrogen bonds other than peptide bonds (3.5) acting on amide bonds in linear amides (3.5.1)

Landscapes

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

Abstract

PURPOSE: To prepare the L-isomer of a phosphorus-containing amino acid, useful as an agricultural and horticultural fungicide and herbicide, by treating the racemic body of the phoshorus-containing amino acid with a specific microbial acylase which is inert to the D-isomer and specifically decomposes the acyl group of the L-isomer.
CONSTITUTION: The racemic compound of N-acyl-D, L-2-amino-4-methylphosphinobutric acid (N-acyl-D,L-MPGA) of formula (R is acyl which may be substituted by halogen) is resolved into L-MPGA and N-acyl-D-MPGA by the action of cultured cells of microorganisms such as bacteria, actinomycetes, or molds, having acyl-decomposing activity, or their treated product, in an aqueous medium. The L-isomer and the D-isomer are separated each other by conventional fractionation. The microorganisms having acyl-decomposing activity, are bacteria belonging to Pseudomonas genus, Actinomycetes belonging to Streptomyces genus, or molds belonging to Aspergillus genus.
COPYRIGHT: (C)1980,JPO&Japio
JP12039078A 1978-10-02 1978-10-02 Optical resolution of phosphorus-containing amino acid Granted JPS5547630A (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
JP12039078A JPS5547630A (en) 1978-10-02 1978-10-02 Optical resolution of phosphorus-containing amino acid
GB7933176A GB2031896B (en) 1978-10-02 1979-09-25 Process for the optical resolution of d,l-2-amino-4-methylphosphinobutyric acid
FR7925384A FR2438054A1 (en) 1978-10-02 1979-09-27 OPTICAL SPLITTING OF D, L-2-AMINO-4-METHYL-PHOSPHINOBUTYRIC ACID
DE2939269A DE2939269C2 (en) 1978-10-02 1979-09-28 Process for the optical separation of DL-2-amino-4-hydroxy (methyl) phosphinoylbutyric acid

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP12039078A JPS5547630A (en) 1978-10-02 1978-10-02 Optical resolution of phosphorus-containing amino acid

Publications (2)

Publication Number Publication Date
JPS5547630A true JPS5547630A (en) 1980-04-04
JPS6247520B2 JPS6247520B2 (en) 1987-10-08

Family

ID=14785011

Family Applications (1)

Application Number Title Priority Date Filing Date
JP12039078A Granted JPS5547630A (en) 1978-10-02 1978-10-02 Optical resolution of phosphorus-containing amino acid

Country Status (4)

Country Link
JP (1) JPS5547630A (en)
DE (1) DE2939269C2 (en)
FR (1) FR2438054A1 (en)
GB (1) GB2031896B (en)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3048612C2 (en) * 1980-12-23 1982-12-02 Hoechst Ag, 6000 Frankfurt "Process for the enzymatic separation of L-2-Ami no-4-methylphosphinobutyric acid"
JPS59219297A (en) * 1983-05-27 1984-12-10 Meiji Seika Kaisha Ltd Preparation of optically active ((3-amino-3-carboxy) propyl-1) phosphinic acid derivative
DE3544376A1 (en) * 1985-12-14 1987-06-19 Hoechst Ag DIPEPTIDES WITH C-TERMINAL PHOSPHINOTHRICIN, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE FOR CONTROLLING UNWANTED PLANT GROWTH
JPH0518339Y2 (en) * 1987-05-11 1993-05-17
DE3724722A1 (en) * 1987-07-25 1989-02-16 Hoechst Ag IMPROVED METHOD FOR THE ENZYMATIC PRODUCTION OF L-2-AMINO-4-METHYLPHOSPHINOBUTTERIC ACID
DE3817191A1 (en) * 1988-05-20 1989-11-30 Hoechst Ag METHOD FOR RACEMIZING OPTICALLY ACTIVE D-2-N-PHENACETYLAMINO-4-METHYLPHOSPHINOBUTTERIC ACID
DE3842025A1 (en) * 1988-12-14 1990-07-05 Hoechst Ag PROCESS FOR PREPARING L-PHOSPHINOTHRICINE
DE3903446A1 (en) * 1989-02-06 1990-10-18 Hoechst Ag METHOD FOR ENZYMATICALLY SEPARATING 2-AMINO-4-METHYLPHOSPHINOBUTTERIC ACID DERIVATIVES
EP0499376A1 (en) * 1991-01-31 1992-08-19 Hoechst Celanese Corporation Precipitation-induced asymmetric transformation of chiral alpha-amino acids and salts thereof
DE4422045A1 (en) 1994-06-26 1996-01-04 Hoechst Schering Agrevo Gmbh Process for the enzymatic cleavage of 2-amino-4-methylphosphinobutanoic acid derivatives
WO1997041214A1 (en) * 1996-04-25 1997-11-06 Novartis Ag Biocatalysts with amine acylase activity
DE19933362A1 (en) * 1999-07-20 2001-02-08 Aventis Cropscience Gmbh Process for the production of L-amino acids from their racemic N-acetyl-D, L derivatives by enzymatic racemate cleavage using isolated, recombinant enzymes
AU2003207323B2 (en) * 2002-02-26 2007-09-13 Syngenta Limited A method of selectively producing male or female sterile plants

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3816254A (en) * 1970-02-03 1974-06-11 Tanabe Seiyaku Co Optical resolution of racemic amino acids
JPS5318006B2 (en) * 1973-09-28 1978-06-13
FR2352827A1 (en) * 1976-05-26 1977-12-23 Rhone Poulenc Ind SUPPORT-AMINOACYLASE COMPLEXES

Also Published As

Publication number Publication date
FR2438054A1 (en) 1980-04-30
GB2031896A (en) 1980-04-30
DE2939269A1 (en) 1980-04-30
DE2939269C2 (en) 1982-07-08
FR2438054B1 (en) 1985-02-15
GB2031896B (en) 1983-03-23
JPS6247520B2 (en) 1987-10-08

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