Patent US3907638A successfully refreshed from Google Patents.
US3907638A
Expired / Lapsed
US
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Selective deacylation of N-acyl-DL-amino acids
Assignee: Ajinomoto Co Inc
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Filing: 1974-04-17
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Granted: 1975-09-23
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Expires: 1994-04-17
Abstract
Abstract When N-acyl-DL-amino acids in acid aqueous solution are subjected to acylase which deacylates only one enantiomorph while the aqueous solution is in contact with an organic solvent not miscible with water, the optically active amino acid accumulates in the aqueous phase while the carboxylic acid furnishing the initial acyl group and optically active N-acyl-amino acid accumulates in the organic solvent phase. The amino acid is readily recovered from the aqueous phase, and the enzyme is available for deacylating more N-acyl-DL-amino acid without interference from the compounds transferred to the organic phase.
Inventors
- 👤 Teruo Uzuki
- 👤 Mayumi Takahashi
- 👤 Misa Noda
- 👤 Yoshioki Komachiya
- 👤 Hachiro Wakamatsu
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 13:01
CPC Classifications
C; C12; C12P; C12P13/00; C12P13/04; C12P41/00; C12P41/006; C12P41/007; Y; Y10; Y10S; Y10S435/00; Y10S435/803
Claims Analysis
Total Claims: 12
Claim 1
Independent Claim
137 words
IN A METHOD OF PREPARING AN OPTICALLY ACTIVE AMINO ACID FROM A RACEMIC N-ACYL DERIVATIVE OF SAID AMINO ACID, THE ACYL GROUP BEING THE ACYL RADICAL OF A CARBOXYLIC ACID, WHEREIN SAID RACEMIC N-ACYL DERIVATIVE IS ATTACKED BY ACYLASE IN AN AQUEOUS MEDIUM UNTIL SAID RACEMIC N-ACYL DERIVATIVE IS PARTLY DEACY/ LATED TO AN OPTICALLY ACTIVE ENANTIOMORPH OF SAID AMINO ACID, AND AN OPTICALLY ACTIVE ENANTIOMORPH OF SAID N-ACYL DERIVATIVE AND SAID CARBOXYLIC ACID ARE FORMED, THE IMPROVEMENT WHICH COMPRISES: A. CONTACTING SAID MEDIUM DURING SAID ATTACKING WITH AN ORGANIC SOLVENT NOT MISCIBLE WITH SAID MEDIUM, B. THE RESPECTIVE EQUILIBRIUM CONCENTRATIONS OF SAID RACEMIC N-ACYL DERIVATIVE AND OF SAID CARBOXYLIC ACID IN SAID SOLVENT BEING AT LEAST EQUAL TO THE CORRESPONDING CONCENTRATIONS IN SAID MEDIUM, AND C. THE PH VALUE OF SAID MEDIUM BEING LOWER THAN 7
Claim 2
Dependent Claim
137 words
IN A METHOD OF PREPARING AN OPTICALLY ACTIVE AMINO ACID FROM A RACEMIC N-ACYL DERIVATIVE OF SAID AMINO ACID, THE ACYL GROUP BEING THE ACYL RADICAL OF A CARBOXYLIC ACID, WHEREIN SAID RACEMIC N-ACYL DERIVATIVE IS ATTACKED BY ACYLASE IN AN AQUEOUS MEDIUM UNTIL SAID RACEMIC N-ACYL DERIVATIVE IS PARTLY DEACY/ LATED TO AN OPTICALLY ACTIVE ENANTIOMORPH OF SAID AMINO ACID, AND AN OPTICALLY ACTIVE ENANTIOMORPH OF SAID N-ACYL DERIVATIVE AND SAID CARBOXYLIC ACID ARE FORMED, THE IMPROVEMENT WHICH COMPRISES: A. CONTACTING SAID MEDIUM DURING SAID ATTACKING WITH AN ORGANIC SOLVENT NOT MISCIBLE WITH SAID MEDIUM, B. THE RESPECTIVE EQUILIBRIUM CONCENTRATIONS OF SAID RACEMIC N-ACYL DERIVATIVE AND OF SAID CARBOXYLIC ACID IN SAID SOLVENT BEING AT LEAST EQUAL TO THE CORRESPONDING CONCENTRATIONS IN SAID MEDIUM, AND C. THE PH VALUE OF SAID MEDIUM BEING LOWER THAN 7
Claim 3
Dependent Claim
16 words
In a method as set forth in claim 1, said pH value being at least 3.5.
Claim 4
Dependent Claim
19 words
In a method as set forth in claim 2, said solvent and said medium being agitated during said contacting.
Claim 5
Dependent Claim
24 words
In a method as set forth in claim 3, the volume of said solvent being at least 70% of the volume of said medium.
Claim 6
Dependent Claim
43 words
In a method as set forth in claim 4, the temperature of said medium being between 20* and 60*C, the concentration of said racemic N-acyl derivative in said aqueous medium prior to said attack being between 5 g and 60 g per deciliter.
Claim 7
Dependent Claim
86 words
In a method as set forth in claim 1, said solvent being a liquid triester of phosphoric acid, a lower alkyl ester of a lower alkanoic acid, a dialkyl ketone, or an alcohol, said triester having three alkyl groups jointly having five to 15 carbon atoms, said lower alkyl ester having one to four carbon atoms in the alcohol moiety thereof and two to four carbon atoms in the acid moiety, said dialkyl ketone and said alcohol having at least four carbon atoms and being liquid.
Claim 8
Dependent Claim
69 words
In a method as set forth in claim 1, said medium being contacted with said solvent until said optically active amino acid accumulates in said medium and said optically active enantiomorph of said N-acyl derivative and said carboxylic acid accumulates in said solvent, and separating the solvent together with the accumulated optically active enantiomorph of said N-acyl derivative and with said carboxylic acid from said optically active amino acid.
Claim 9
Dependent Claim
56 words
In a method as set forth in claim 7, heating a portion of said separated solvent and the accumulated optically active enantiomorph of said N-acyl derivative until said derivative is racemized, and thereafter contacting said portion of the separated solvent with an aqueous medium containing said acylase until said racemized derivative is deacylated by said acylase.
Claim 10
Dependent Claim
36 words
In a method as set forth in claim 8, said portion Of the separated solvent and the accumulated optically active enantiomorph of said N-acyl derivative being heated at 90* to 200*C until said derivative is racemized.
Claim 11
Dependent Claim
27 words
In a method as set forth in claim 1, said amino acid being valine, leucine, isoleucine, methionine, aspartic acid, glutamic acid, phenylalanine, phenylglycine, 3,4-methylenedihydroxyphenylalanine, 3,4-dimethoxyphenylalanine, and tryptophan.
Claim 12
Dependent Claim
150 words
In a method as set forth in claim 10, the acyl moiety of said N-acyl derivative being acetyl, formyl, chloroacetyl, propionyl, or benzoyl, the volume of said solvent being at least 70% of the volume of said medium, the temperature of said medium being between 20* and 60*C, the concentration of said racemic N-acyl derivative in said aqueous medium prior to said attack being between 5 g and 60 g per deciliter, and said solvent being a liquid triester of phosphoric acid, a lower alkyl ester of a lower alkanoic acid, a dialkyl ketone, or an alcohol, said triester having three alkyl groups jointly having five to fifteen carbon atoms, said lower alkyl ester having one to four carbon atoms in the alcohol moiety thereof and two to four carbon atoms in the acid moiety, said dialkyl ketone and said alcohol having at least four carbon atoms and being liquid.
References Cited (Backward Citations)
US3290225A
Cited
US3669837A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1978-09-22 | 1979-03-24 | 1979-09-23 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1982-09-22 | 1983-03-24 | 1983-09-23 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1986-09-22 | 1987-03-24 | 1987-09-23 | $7700.00 | Window Closed / Lapsed |