US4256836A
Expired / Lapsed
US
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Addition compound of dipeptide derivative and amino acid derivative
Assignee: Sagami Chemical Research Institute
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Filing: 1979-03-13
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Granted: 1981-03-17
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Expires: 1999-03-13
Abstract
Abstract Addition compounds having the formula <IMAGE> (I) wherein R1 represents an aliphatic oxycarbonyl group, benzyloxycarbonyl group which can have nuclear substituents, or benzoyl, aromatic sulfonyl or aromatic sulfinyl group; R2 represents methyl, isopropyl, isobutyl, isoamyl or benzyl group; R3 represents a lower alkoxyl, benzyloxy or benzhydryloxy group and n represents 1 or 2 are produced by reacting an N-substituted monoaminodicarboxylic acid having the formula <IMAGE> (IV) with an amino carboxylic acid ester having the formula <IMAGE> (V) in the presence of a protease.
Inventors
- 👤 Yoshikazu Isowa
- 👤 Muneki Ohmori
- 👤 Kaoru Mori
- 👤 Tetsuya Ichikawa
- 👤 Yuji Nonaka
- 👤 Keiichi Kihara
- 👤 Kiyotaka Oyama
- 👤 Heijiro Satoh
- 👤 Shigeaki Nishimura
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-26 01:34
CPC Classifications
C; C07; C07K; C07K5/00; C07K5/04; C07K5/06; C07K5/06104; C07K5/06113; C07K5/06121; C07K5/0613
Claims Analysis
Total Claims: 22
Claim 1
Independent Claim
121 words
A process for producing an addition compound having the formula ##STR10## wherein R 1 represents an aliphatic oxycarbonyl group, benzyloxycarbonyl group which can have nuclear substituents, or benzoyl, aromatic sulfonyl or aromatic sulfinyl group; R 2 represents methyl, isopropyl, isobutyl, isoamyl or benzyl group; R 3 represents a lower alkoxyl, benzyloxy, benzhydryloxy group and n represents 1 or 2 which comprises reacting an N-substituted monoaminodicarboxylic acid having the formula ##STR11## with an amino carboxylic acid ester having the formula ##STR12## in an aqueous medium in the presence of a protease in a pH range wherein the protease exerts enzymatic activity and reacting the resulting dipeptide ester with the amino carboxylic acid ester thereby depositing the addition compound and separating the same.
Claim 2
Dependent Claim
121 words
A process for producing an addition compound having the formula ##STR10## wherein R 1 represents an aliphatic oxycarbonyl group, benzyloxycarbonyl group which can have nuclear substituents, or benzoyl, aromatic sulfonyl or aromatic sulfinyl group; R 2 represents methyl, isopropyl, isobutyl, isoamyl or benzyl group; R 3 represents a lower alkoxyl, benzyloxy, benzhydryloxy group and n represents 1 or 2 which comprises reacting an N-substituted monoaminodicarboxylic acid having the formula ##STR11## with an amino carboxylic acid ester having the formula ##STR12## in an aqueous medium in the presence of a protease in a pH range wherein the protease exerts enzymatic activity and reacting the resulting dipeptide ester with the amino carboxylic acid ester thereby depositing the addition compound and separating the same.
Claim 3
Dependent Claim
24 words
A process according to claim 1, wherein R 1 is benzyloxycarbonyl or N-p-methoxycarbonyl, R 2 is benzyl and R 3 is methoxy or ethoxy.
Claim 4
Dependent Claim
10 words
A process according to claim 2, wherein n is 1.
Claim 5
Dependent Claim
10 words
A process according to claim 2, wherein n is 2.
Claim 6
Dependent Claim
14 words
A process according to claim 1, wherein the aqueous medium is an aqueous solution.
Claim 7
Dependent Claim
43 words
A process according to claim 1, wherein the N-substituted monoaminodicarboxylic acid and the amino acid ester being in a molar ratio ranging from about 5:1 to about 1:5 are subjected to the reaction in concentration ranging from about 0.1 to about 4 M.
Claim 8
Dependent Claim
12 words
A process according to claim 1, wherein the protease is a metalloprotease.
Claim 9
Dependent Claim
35 words
A process according to claim 7, wherein the metalloprotease is used in an amount ranging from about 2 to about 400 mg per one millimole of the N-substituted monoaminodicarboxylic acid and the amino acid ester.
Claim 10
Dependent Claim
30 words
A process according to claim 1, wherein the reaction is carried out at pH of 5 to 8 in a temperature range from about 20° C. to about 50° C.
Claim 11
Dependent Claim
102 words
A process according to claim 2, wherein the aqueous medium is an aqueous solution in which the N-substituted monoaminodicarboxylic acid and the amino acid ester are in a molar ratio ranging from about 5:1 to about 1:5 with concentrations ranging from about 0.1 to about 4 M and the protease is a metalloprotease used in an amount ranging from about 2 to about 400 mg per one millimole of said both starting materials and further the reaction is carried out in a temperature range from about 20° C. to 50° C. and in a pH range from about 5 to about 8.
Claim 12
Dependent Claim
10 words
A process according to claim 10, wherein n is 1.
Claim 13
Dependent Claim
10 words
A process according to claim 10, wherein n is 2.
Claim 14
Dependent Claim
20 words
A process according to claim 1 wherein the N-substituted monoaminodicarboxylic acid and the aminocarboxylic acid ester are both in L-form.
Claim 15
Dependent Claim
22 words
A process according to claim 1 wherein the N-substituted monoaminodicarboxylic acid and the amino acid ester are in L-form and DL-form, respectively.
Claim 16
Dependent Claim
22 words
A process according to claim 1 wherein the N-substituted monoaminodicarboxylic acid and the amino acid ester are in DL-form and L-form, respectively.
Claim 17
Dependent Claim
20 words
A process according to claim 1 wherein the N-substituted monoaminodicarboxylic acid and the amino acid ester are both in DL-form.
Claim 18
Dependent Claim
20 words
A process according to claim 10, wherein the N-substituted monoaminodicarboxylic acid and the aminocarboxylic acid ester are both in L-form.
Claim 19
Dependent Claim
22 words
A process according to claim 10, wherein the N-substituted monoaminodicarboxylic acid and the aminocarboxylic acid ester are in L-form and DL-form, respectively.
Claim 20
Dependent Claim
22 words
A process according to claim 10, wherein the N-substituted monoaminodicarboxylic acid and the amino acid ester are in DL-form and L-form, respectively.
Claim 21
Dependent Claim
20 words
A process according to claim 10, wherein the N-substituted monoaminodicarboxylic acid and the amino acid ester are both in DL-form.
Claim 22
Dependent Claim
10 words
A process according to claim 18, wherein n is 1.
References Cited (Backward Citations)
US3786039A
Cited
US3853835A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1984-03-16 | 1984-09-15 | 1985-03-17 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-03-16 | 1988-09-15 | 1989-03-17 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1992-03-16 | 1992-09-15 | 1993-03-17 | $7700.00 | Window Closed / Lapsed |