US4226941A
Expired / Lapsed
US
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Process for the optical resolution of d,l-2-amino-4-methylphosphinobutyric acid
Assignee: Meiji Seika Kaisha Ltd
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Filing: 1979-09-27
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Granted: 1980-10-07
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Expires: 1999-09-27
Abstract
Abstract L-2-Amino-4-methylphosphinobutyric acid (L-MPGA) which is useful as bactericide and herbicide can be prepared by optical resolution of its racemic mixture, D,L-MPGA with the action of a microbial acylase. The process comprises providing D,L-MPGA in the form of its N-acyl derivative, reacting N-acyl-D,L-MPGA in an aqueous medium with a microbial acylase having an optically specific hydrolytic activity, whereby selectively eliminating the acyl group of N-acyl-L-MPGA to give a mixture of L-MPGA and N-acyl-D-MPGA and isolating L-MPGA from the mixture. The acylase is produced by cultivating a microbial strain belonging to the genus Pseudomonas, Streptomyces or Aspergillus, particularly Pseudomonas maltophilia BN-233, Streptomyces violascens SF 2072, Streptomyces diastatochromogenes SF 2073, Aspergillus sp. KS-101 or Aspergillus sp. KS-102.
Inventors
- 👤 Hitoshi Goi
- 👤 Shinji Miyado
- 👤 Takashi Shomura
- 👤 Akira Suzuki
- 👤 Tomizo Niwa
- 👤 Yujiro Yamada
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-30 05:49
CPC Classifications
C; C07; C07F; C07F9/00; C07F9/02; C07F9/28; C07F9/30; C07F9/301; C12; C12N; C12N1/00; C12N1/14; C12N1/145; C12N1/20; C12N1/205; C12P; C12P13/00; C12P13/04; C12R; C12R2001/00; C12R2001/01; C12R2001/38; C12R2001/465; C12R2001/645; C12R2001/66
Claims Analysis
Total Claims: 16
Claim 1
Independent Claim
89 words
A process for the optical resolution of D,L-2-amino-4-methylphosphinobutyric acid which comprises the steps of: providing D,L-2-amino-4-methylphosphinobutyric acid in the form of its N-acyl derivative; reacting the N-acyl derivative of D,L-2-amino-4-methylphosphinobutyric acid in an aqueous medium with a microbial acylase having an optically specific hydrolytic activity which is produced by cultivating a microbial strain belonging to the genus Pseudomonas, Streptomyces or Aspergillus; whereby selectively eliminating the acyl group of N-acyl-L-2-amino-4-methylphosphinobutyric acid to give a mixture of L-2-amino-4-methylphosphinobutyric acid and N-acyl-D-2-amino-4-methylphosphinobutyric acid; and isolating and recovering L-2-amino-4-methylphosphinobutyric acid from the mixture.
Claim 2
Dependent Claim
89 words
A process for the optical resolution of D,L-2-amino-4-methylphosphinobutyric acid which comprises the steps of: providing D,L-2-amino-4-methylphosphinobutyric acid in the form of its N-acyl derivative; reacting the N-acyl derivative of D,L-2-amino-4-methylphosphinobutyric acid in an aqueous medium with a microbial acylase having an optically specific hydrolytic activity which is produced by cultivating a microbial strain belonging to the genus Pseudomonas, Streptomyces or Aspergillus; whereby selectively eliminating the acyl group of N-acyl-L-2-amino-4-methylphosphinobutyric acid to give a mixture of L-2-amino-4-methylphosphinobutyric acid and N-acyl-D-2-amino-4-methylphosphinobutyric acid; and isolating and recovering L-2-amino-4-methylphosphinobutyric acid from the mixture.
Claim 3
Dependent Claim
18 words
A process according to claim 1 wherein the microbial strain is a strain of the species Pseudomonas maltophilia.
Claim 4
Dependent Claim
21 words
A process according to claim 2 wherein the strain is Pseudomonas maltophilia BN-233 identified as FERM-P 4487 or ATCC No. 31559.
Claim 5
Dependent Claim
18 words
A process according to claim 1 wherein the microbial strain is a strain of the species Streptomyces violascens.
Claim 6
Dependent Claim
21 words
A process according to claim 4 wherein the strain is Streptomyces violascens SF-2072 identified as FERM-P 4617 and ATCC No. 31560.
Claim 7
Dependent Claim
18 words
A process according to claim 1 wherein the microbial strain is a strain of the species Streptomyces diastatochromogenes.
Claim 8
Dependent Claim
21 words
A process according to claim 6 wherein the strain is Streptomyces diastatochromogenes SF-2073 identified as FERM-P 4618 and ATCC No. 31561.
Claim 9
Dependent Claim
18 words
A process according to claim 1 wherein the microbial strain is a strain of the species Aspergillus niger.
Claim 10
Dependent Claim
21 words
A process according to claim 8 wherein the strain is Aspergillus sp. KS-101 identified as FERM-P 4614 and ATCC No. 20567.
Claim 11
Dependent Claim
18 words
A process according to claim 1 wherein the microbial strain is a strain of the species Aspergillus flavus-oryzae.
Claim 12
Dependent Claim
21 words
A process according to claim 10 wherein the strain is Aspergillus sp. KS-102 identified as FERM-P 4615 and ATCC No. 20568.
Claim 13
Dependent Claim
39 words
A process according to claim 1 wherein the microbial acylase is used in the form of a culture obtained by the cultivation of a microbial strain stated or an enzyme material derived from the culture by an after-treatment thereof.
Claim 14
Dependent Claim
62 words
A process according to claim 12 wherein the enzyme material is cells collected from the culture in a washed or unwashed form or a dried or undried form, disintegrated cells, their extracts rich in the microbial acylase which are derived by extraction of the disintegrated cells followed by purification or immobilized acylase preparations derived from the cells, disintegrated cells or their extracts.
Claim 15
Dependent Claim
50 words
A process according to claim 1 wherein the microbial acylase is produced by the cultivation of a microbial strain stated under aerobic conditions in a suitable culture medium at a temperature of 25°-37° C. for a period of time at which the activity of acylase produced reaches a maximum level.
Claim 16
Dependent Claim
40 words
A process according to claim 1 wherein the unreacted N-acyl-D-2-amino-4-methylphosphinobutyric acid is recovered from the reaction mixture and racemized in a known manner to produce a further amount of N-acyl-D,L-2-amino-4-methylphosphinobutyric acid for recycling to the reaction with the microbial acylase.
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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) | 1983-10-07 | 1984-04-07 | 1984-10-07 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-10-07 | 1988-04-07 | 1988-10-07 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-10-07 | 1992-04-07 | 1992-10-07 | $7700.00 | Window Closed / Lapsed |