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US3964970A
Expired / Lapsed
US
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Process for the preparation of L-car-bamyl-amino acids and of the corresponding L-amino acids
Assignee: Anic SpA
•
Filing: 1974-05-10
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Granted: 1976-06-22
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Expires: 1994-05-10
Abstract
Abstract A process for the preparation of only one of the two stereoisomer forms carbamyl amino acids is provided wherein certain heterocyclic compounds having an assymmetrical carbon, such as 5-substituted hydantoins, are hydrolyzed in the presence of certain enzymes, such as dihydropyrimidinase extracted from calf liver. In another embodiment of the invention, the corresponding amino acids are provided by hydrolyzing the carbamyl amino acids in the presence of these same enzymes.
Inventors
- 👤 Dino Dinelli
- 👤 Franco Morisi
- 👤 Delio Zaccardelli
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-03 09:09
CPC Classifications
C; C12; C12P; C12P13/00; C12P13/04; C12P41/00; C12P41/006; C12P41/009
Claims Analysis
Total Claims: 24
Claim 1
Independent Claim
116 words
A process for the preparation of only one of the two stereoisomer forms of carbamylamino acids comprising: a. subjecting to hydrolysis a racemic mixture of compounds of the formula ##EQU4## wherein X is selected from the group consisting of CO, CS and O, R is selected from the group consisting of hydrogen and hydrocarbon radicals having up to 8 carbon atoms, R 1 is the residue of an amino acid molecule wherefrom the ##EQU5## moiety has been removed, said hydrolysis being carried out in the presence of an enzyme which acts on the racemic mixture through a selective hydrolysis of only one of the optically active forms: b. separating the sole resultant carbamyl amino acid stereoisomer.
Claim 2
Dependent Claim
116 words
A process for the preparation of only one of the two stereoisomer forms of carbamylamino acids comprising: a. subjecting to hydrolysis a racemic mixture of compounds of the formula ##EQU4## wherein X is selected from the group consisting of CO, CS and O, R is selected from the group consisting of hydrogen and hydrocarbon radicals having up to 8 carbon atoms, R 1 is the residue of an amino acid molecule wherefrom the ##EQU5## moiety has been removed, said hydrolysis being carried out in the presence of an enzyme which acts on the racemic mixture through a selective hydrolysis of only one of the optically active forms: b. separating the sole resultant carbamyl amino acid stereoisomer.
Claim 3
Dependent Claim
55 words
The process of claim 1 further comprising the steps of: c. racemizing the hydrolysis product remaining after said carbamyl amino acid is separated, and d. subjecting the racemic mixture resulting from step (c) to hydrolysis in the presence of an enzyme used in step (a); and e. separating the sole resultant carbamyl amino acid stereoisomer.
Claim 4
Dependent Claim
23 words
The process of claim 1 which further comprises the step of converting said carbamyl amino acid stereoisomer obtained to the corresponding amino acid.
Claim 5
Dependent Claim
23 words
The process of claim 2 which further comprises the step of converting said carbamyl amino acid stereoisomer obtained to the corresponding amino acid.
Claim 6
Dependent Claim
9 words
The process of claim 1 wherein X is CO.
Claim 7
Dependent Claim
9 words
The process of claim 2 wherein X is CO.
Claim 8
Dependent Claim
14 words
The process of claim 2 wherein said enzyme is dihydropyrimidinase extracted from calf liver.
Claim 9
Dependent Claim
32 words
The process according to claim 2 wherein X is CO; said racemizing in step (c) is carried out in an aqueous solution at a racemizing temperature and at a pH above 7.
Claim 10
Dependent Claim
20 words
The process according to claim 1 wherein said enzymes are bound to a carrier or englobed in a fibrous carrier.
Claim 11
Dependent Claim
38 words
The process according to claim 3 wherein said carbamyl amino acid is converted into the corresponding amino acid by heating said carbamyl amino acid in an aqueous solution and gradually adding thereto an equimolecular amount of an acid.
Claim 12
Dependent Claim
26 words
The process according to claim 2 wherein said racemizing of the hydrolysis product is carried out without any previous separation of the carbamyl amino acid stereoisomer.
Claim 13
Dependent Claim
20 words
The process according to claim 2 wherein said racemization is carried out simultaneously with the enzymatic hydrolysis of step (d).
Claim 14
Dependent Claim
15 words
The process according to claim 1 wherein said enzyme is dihydropyrimidinase extracted from calf liver.
Claim 15
Dependent Claim
14 words
The process of claim 11 wherein said enzyme is dihydropyrimidinase extracted from calf liver.
Claim 16
Dependent Claim
14 words
The process of claim 12 wherein said enzyme is dihydropyrimidinase extracted from calf liver.
Claim 17
Dependent Claim
18 words
The process of claim 1 wherein X is CO and said enzyme is dihydropyrimidinase extracted from calf liver.
Claim 18
Dependent Claim
18 words
The proces of claim 2 wherein X is CO and said enzyme is dihydropyrimidinase extracted from calf liver.
Claim 19
Dependent Claim
18 words
The process of claim 3 wherein X is CO and said enzyme is dihydropyrimidinase extracted from calf liver.
Claim 20
Dependent Claim
18 words
The process of claim 4 wherein X is CO and said enzyme is dihydropyrimidinase extracted from calf liver.
Claim 21
Dependent Claim
24 words
The process of claim 1 wherein X is CO; R 1 is methyl or isopropyl; and said enzyme is dihydropyrimidinase extracted from calf liver.
Claim 22
Dependent Claim
24 words
The process of claim 2 wherein X is CO; R 1 is methyl or isopropyl; and said enzyme is dihydropyrimidinase extracted from calf liver.
Claim 23
Dependent Claim
24 words
The process of claim 3 wherein X is CO; R 1 is methyl or isopropyl; and said enzyme is dihydropyrimidinase extracted from calf liver.
Claim 24
Dependent Claim
24 words
The process of claim 4 wherein X is CO; R 1 is methyl or isopropyl; and said enzyme is dihydropyrimidinase extracted from calf liver.
References Cited (Backward Citations)
US3320135A
Cited
US3494831A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1979-06-22 | 1979-12-22 | 1980-06-22 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-06-22 | 1983-12-22 | 1984-06-22 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-06-22 | 1987-12-22 | 1988-06-22 | $7700.00 | Window Closed / Lapsed |