US4260684A
Expired / Lapsed
US
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Stereoselective resolution of phenylglycine derivatives and 4-hydroxyphenylglycine derivatives with enzyme resins
Assignee: Bayer AG
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Filing: 1979-02-01
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Granted: 1981-04-07
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Expires: 1999-02-01
Abstract
Abstract The invention relates to a new enzymatic process for the stereoselective resolution of a DL-phenylglycine derivative comprising hydrolyzing an ester or amide group on an N-acyl-L-phenylglycine ester or amide in an N-acyl-DL-phenylglycine ester or amide in solution by the action of an enzyme bonded to a carrier, separating the N-acyl-D-phenylglycine ester or amide from the N-acyl-L-phenylglycine and then, if desired, hydrolyzing under acid conditions, the ester or amide group of the D-enantiomer and the acyl group. D-Phenylglycine and D-4-hydroxyphenylglycine are used as starting substances for the preparation of semisynthetic antibiotics of the penicillin series. L-Phenylglycine is a starting substance for L-aspartyl-L-phenylglycine methyl ester, which is used as a sweetener.
Inventors
- 👤 Hermann Schutt
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-26 15:39
CPC Classifications
C; C12; C12P; C12P41/00; C12N; C12N11/00; C12N11/02; C12P13/00; C12P13/04
Claims Analysis
Total Claims: 15
Claim 1
Independent Claim
79 words
A process for the stereoselective resolution of a DL-phenylglycine derivative which comprises hydrolyzing at 20° to 40° C. and at a pH range of 6 to 8 an ester or amide group on an N-acyl-L-phenylglycine ester or amide in an N-acyl-DL-phenylglycine ester or amide in solution by the action of an enzyme bonded to a carrier to form a mixture of .sup.(1) N-acyl-L-phenylglycine and .sup.(2) N-acyl-D-phenylglycine ester or amide and separating the N-acyl-D-phenylglycine ester or amide from the N-acyl-L-phenylglycine.
Claim 2
Dependent Claim
79 words
A process for the stereoselective resolution of a DL-phenylglycine derivative which comprises hydrolyzing at 20° to 40° C. and at a pH range of 6 to 8 an ester or amide group on an N-acyl-L-phenylglycine ester or amide in an N-acyl-DL-phenylglycine ester or amide in solution by the action of an enzyme bonded to a carrier to form a mixture of .sup.(1) N-acyl-L-phenylglycine and .sup.(2) N-acyl-D-phenylglycine ester or amide and separating the N-acyl-D-phenylglycine ester or amide from the N-acyl-L-phenylglycine.
Claim 3
Dependent Claim
14 words
A process according to claim 1 in which the enzyme is a proteolytic enzyme.
Claim 4
Dependent Claim
16 words
A process according to claim 2 in which the enzyme is a serine protease or sulphydryl-protease.
Claim 5
Dependent Claim
17 words
A process according to claim 1, in which the enzyme is subtilisin, α-chymotrypsin, papain, ficin or bromelain.
Claim 6
Dependent Claim
22 words
A process of claim 1 wherein the ester or amide group in the N-acyl-D-phenylglycine ester or amide is hydrolyzed under acid conditions.
Claim 7
Dependent Claim
28 words
A process according to claim 1 in which the carrier for the enzyme is a copolymer of a methacrylate, methacrylic acid and maleic anhydride, optionally crosslinked by glutardialdehyde.
Claim 8
Dependent Claim
29 words
A process according to claim 4, in which the carrier for the enzyme is a copolymer of tetraethylene glycol dimethacrylate, methacrylic acid and maleic anhydride, optionally crosslinked by glutardialdehyde.
Claim 9
Dependent Claim
14 words
A process according to claim 4 in which the enzyme is subtilisin (EC 3.4.4.16).
Claim 10
Dependent Claim
14 words
A process according to claim 4 in which the enzyme is α-chymotrypsin (EC 3.4.4.5).
Claim 11
Dependent Claim
14 words
A process according to claim 4 in which the enzyme is papain (EC 3.4.4.10).
Claim 12
Dependent Claim
91 words
A process according to claim 1, in which the DL-phenylglycine derivative corresponds to the formula ##STR2## in which R 1 denotes a hydrogen atom or a radical of an optionally substituted aliphatic or araliphatic monocarboxylic or dicarboxylic acid or of a naturally occurring or synthetic α-aminocarboxylic acid, R 2 denotes an alkoxy group, an amino group which is optionally monosubstituted or disubstituted by alkyl, or a radical of a naturally occurring or synthetic α-aminoacid and R 3 denotes a hydrogen atom or a hydroxyl, alkoxy, aralkoxy, aryloxy, cycloalkoxy or acyloxy group.
Claim 13
Dependent Claim
47 words
A process according to claim 1, in which the DL-phenylglycine derivative corresponds to the formula ##STR3## in which R 1 denotes a hydrogen atom or a mono-, di- or tri-chloromethyl, trifluoromethyl or w-carboxy-C 2 -C 6 -alkyl group and R 2 denotes a methoxy or ethoxy group.
Claim 14
Dependent Claim
58 words
A process according to claim 1, in which the DL-phenylglycine derivative corresponds to the formula ##STR4## in which R 1 denotes a hydrogen atom or a methyl, mono-, di- or tri-chloromethyl, trifluoromethyl or w-carboxy-C 2 -C 6 -alkyl group, R 2 denotes a methoxy or ethoxy group and R 3 denotes a hydroxyl, methoxy, ethoxy or acetoxy group.
Claim 15
Dependent Claim
46 words
A process according to claim 11, in which R 1 denotes a hydrogen atom or a radical of an aliphatic or araliphatic monocarboxylic or dicarboxylic acid or of a naturally occurring or synthetic α-aminocarboxylic acid and R 3 denotes a hydrogen atom or a hydroxyl group.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1984-04-06 | 1984-10-06 | 1985-04-07 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-04-06 | 1988-10-06 | 1989-04-07 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1992-04-06 | 1992-10-06 | 1993-04-07 | $7700.00 | Window Closed / Lapsed |