GB1369462A - Enzymic resolution of racemic n-acyl-dl-amino acids - Google Patents

Enzymic resolution of racemic n-acyl-dl-amino acids

Info

Publication number
GB1369462A
GB1369462A GB5427971A GB5427971A GB1369462A GB 1369462 A GB1369462 A GB 1369462A GB 5427971 A GB5427971 A GB 5427971A GB 5427971 A GB5427971 A GB 5427971A GB 1369462 A GB1369462 A GB 1369462A
Authority
GB
United Kingdom
Prior art keywords
acyl
racemic
acid
give
amino acids
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
GB5427971A
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.)
Beecham Group PLC
Original Assignee
Beecham Group PLC
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 Beecham Group PLC filed Critical Beecham Group PLC
Priority to GB5427971A priority Critical patent/GB1369462A/en
Publication of GB1369462A publication Critical patent/GB1369462A/en
Expired 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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • 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

Abstract

1369462 Enzymic resolution of racemic N-acyl- DL-amino acids BEECHAM GROUP Ltd 23 Nov 1971 54279/71 Heading C2C A racemic acid of the formula where R is an alkyl, aryl or aralkyl group, each of which may be substituted, and R 1 is an acyl group, except that when R is phenyl, R 1 is not phenylacetyl, is resolved by treating in aqueous medium with a deacylase enzyme known to remove the N-acyl side chain of a penicillin to give 6-aminopenicillanic acid, to give the free L-amino acid and separating this from the N- acyl-D-amino acid. The latter is then subjected to acid hydrolysis to give the free D-amino acid. The deacylase enzyme is preferably derived from a suitable strain of Escherichia Coli and may be in a water-insoluble form.
GB5427971A 1971-11-23 1971-11-23 Enzymic resolution of racemic n-acyl-dl-amino acids Expired GB1369462A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB5427971A GB1369462A (en) 1971-11-23 1971-11-23 Enzymic resolution of racemic n-acyl-dl-amino acids

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB5427971A GB1369462A (en) 1971-11-23 1971-11-23 Enzymic resolution of racemic n-acyl-dl-amino acids

Publications (1)

Publication Number Publication Date
GB1369462A true GB1369462A (en) 1974-10-09

Family

ID=10470489

Family Applications (1)

Application Number Title Priority Date Filing Date
GB5427971A Expired GB1369462A (en) 1971-11-23 1971-11-23 Enzymic resolution of racemic n-acyl-dl-amino acids

Country Status (1)

Country Link
GB (1) GB1369462A (en)

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0003786A1 (en) * 1978-02-21 1979-09-05 Bayer Ag Stereoselective separation of phenylglycine derivatives and 4-hydroxyphenylglycine derivatives with enzyme-containing polymers
WO1980000921A1 (en) * 1978-11-13 1980-05-15 Elf Aquitaine Aqueous micro emulsions of organic substances
EP0054897A2 (en) 1980-12-23 1982-06-30 Hoechst Aktiengesellschaft Process for the enzymatic preparation of L-2-amino-4-methyl-phosphino-butyric acid
EP0137372A1 (en) * 1983-09-27 1985-04-17 Hoechst Aktiengesellschaft Process for the preparation of the optic antipodes of tertiary leucine
US4638086A (en) * 1983-09-27 1987-01-20 Hoechst Aktiengesellschaft Process for the racemization of optically active aminoacids
US4699879A (en) * 1983-11-04 1987-10-13 Zaidan Hojin Biseibutsu Kagaku Kenkyu Kai Process for microbial production of an optically active 3-(3,4-dihydroxyphenyl)serine
EP0301391A1 (en) * 1987-07-25 1989-02-01 Hoechst Aktiengesellschaft Process for the enzymatic production of L-2-amino-4-methyl-phosphinobutyric acid
US4859602A (en) * 1984-09-25 1989-08-22 Boehringer Mannheim Gmbh Process for the preparation of stereoisomers of 1-aminoalkylphosphonic and phosphinic acids
US5057607A (en) * 1990-06-08 1991-10-15 Eli Lilly And Company Enantiomerically selective biocatalyzed acylation

Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0003786A1 (en) * 1978-02-21 1979-09-05 Bayer Ag Stereoselective separation of phenylglycine derivatives and 4-hydroxyphenylglycine derivatives with enzyme-containing polymers
DE2953276C2 (en) * 1978-11-13 1986-05-22 Société Nationale Elf Aquitaine (Production) S.A., Courbevoie N-acyl-α-amino acid salts and their use as surface active agents for the preparation of aqueous microemulsions of hydrocarbons
WO1980000921A1 (en) * 1978-11-13 1980-05-15 Elf Aquitaine Aqueous micro emulsions of organic substances
FR2468402A2 (en) * 1978-11-13 1981-05-08 Elf Aquitaine AQUEOUS MICROEMULSIONS OF ORGANIC SUBSTANCES
US4404109A (en) 1978-11-13 1983-09-13 Societe Nationale Elf Aquitaine (Production) Aqueous micro-emulsions of organic substances
EP0054897A2 (en) 1980-12-23 1982-06-30 Hoechst Aktiengesellschaft Process for the enzymatic preparation of L-2-amino-4-methyl-phosphino-butyric acid
EP0054897A3 (en) * 1980-12-23 1982-09-08 Hoechst Aktiengesellschaft Process for the enzymatic preparation of l-2-amino-4-methyl-phosphino-butyric acid
EP0137372A1 (en) * 1983-09-27 1985-04-17 Hoechst Aktiengesellschaft Process for the preparation of the optic antipodes of tertiary leucine
US4638086A (en) * 1983-09-27 1987-01-20 Hoechst Aktiengesellschaft Process for the racemization of optically active aminoacids
AU573261B2 (en) * 1983-09-27 1988-06-02 Hoechst A.G. Preparation of tert-leucine
US4699879A (en) * 1983-11-04 1987-10-13 Zaidan Hojin Biseibutsu Kagaku Kenkyu Kai Process for microbial production of an optically active 3-(3,4-dihydroxyphenyl)serine
US4859602A (en) * 1984-09-25 1989-08-22 Boehringer Mannheim Gmbh Process for the preparation of stereoisomers of 1-aminoalkylphosphonic and phosphinic acids
EP0301391A1 (en) * 1987-07-25 1989-02-01 Hoechst Aktiengesellschaft Process for the enzymatic production of L-2-amino-4-methyl-phosphinobutyric acid
US5057607A (en) * 1990-06-08 1991-10-15 Eli Lilly And Company Enantiomerically selective biocatalyzed acylation

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Legal Events

Date Code Title Description
PS Patent sealed
PCNP Patent ceased through non-payment of renewal fee