US3997516A
Expired / Lapsed
US
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Method for protecting guanidino group and restoring the same
Assignee: Takeda Pharmaceutical Co Ltd
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Filing: 1975-06-27
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Granted: 1976-12-14
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Expires: 1995-06-27
Abstract
Abstract A guanidino group in an amino acid or a peptide can be protected with a specific protective group, i.e. lower alkoxybenzenesulfonyl group or tri-lower alkylbenzenesulfonyl group, and the protective group may easily be removed without affecting the amino acid or the peptide to be derived from the protected amino acid or peptide. Thus, the method is useful in the related chemical industries, especially in the peptide synthesis.
Inventors
- 👤 Osamu Nishimura
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-01 04:03
CPC Classifications
C; C07; C07K; C07K1/00; C07K1/02; C07K1/06; C07K1/061; C07K1/064; C07K5/00; C07K5/04; C07K5/10; C07K5/1002; C07K5/1005; Y; Y02; Y02P; Y02P20/00; Y02P20/50; Y02P20/55
Claims Analysis
Total Claims: 19
Claim 1
Independent Claim
42 words
In an amino acid having a protected guanidino group or a peptide containing the residue of an amino acid having a protected guanidino group the improvement according to which the protective grouping is a lower alkoxybenzenesulfonyl group or a tri-lower alkylbenzenesulfonyl group.
Claim 2
Dependent Claim
42 words
In an amino acid having a protected guanidino group or a peptide containing the residue of an amino acid having a protected guanidino group the improvement according to which the protective grouping is a lower alkoxybenzenesulfonyl group or a tri-lower alkylbenzenesulfonyl group.
Claim 3
Dependent Claim
16 words
An amino acid or peptide as claimed in claim 1, wherein the amino acid is arginine.
Claim 4
Dependent Claim
22 words
An amino acid or peptide as claimed in claim 1, wherein the lower alkoxybenzenesulfonyl group is of one to three carbon atoms.
Claim 5
Dependent Claim
19 words
An amino acid or peptide as claimed in claim 1, wherein the lower alkoxybenzenesulfonyl group is the methoxybenzenesulfonyl group.
Claim 6
Dependent Claim
19 words
An amino acid or peptide as claimed in claim 1, wherein the lower alkoxybenzenesulfonyl group is the p-methoxybenzenesulfonyl group.
Claim 7
Dependent Claim
22 words
An amino acid or peptide as claimed in claim 1, wherein the tri-lower alkylbenzenesulfonyl group is of one to five carbon atoms.
Claim 8
Dependent Claim
19 words
An amino acid or peptide as claimed in claim 1, wherein the tri-lower alkylbenzenesulfonyl group is the tri-methylbenzenesulfonyl group.
Claim 9
Dependent Claim
19 words
An amino acid or peptide as claimed in claim 1, wherein the tri-lower alkylbenzenesulfonyl group is the 2,4,6-tri-methylbenzenesulfonyl group.
Claim 10
Dependent Claim
19 words
An amino acid or peptide as claimed in claim 1, wherein the tri-lower alkylbenzenesulfonyl group is the 2,4,6triisopropylbenzenesulfonyl group.
Claim 11
Dependent Claim
19 words
An amino acid or peptide as claimed in claim 1, wherein the tri-lower alkylbenzenesulfonyl group is the 2,4,6,-triisopropylbenzenesulfonyl group.
Claim 12
Dependent Claim
12 words
A peptide as claimed in claim 1, wherein the peptide is bradykinin.
Claim 13
Dependent Claim
15 words
A peptide as claimed in claim 1, wherein the peptide is of the formula (Pyr)Glu-Trp-Pro-Arg-Pro-Gln-Ileu-Pro-Pro-OH
Claim 14
Dependent Claim
14 words
A peptide as claimed in claim 1, wherein the peptide is luteinizing hormone-releasing hormone.
Claim 15
Dependent Claim
12 words
A peptide as claimed in claim 1, wherein the peptide is tuftsin.
Claim 16
Dependent Claim
15 words
A peptide as claimed in claim 1, wherein the peptide is of the formula H-Thr-Lys-Arg-OH.
Claim 17
Dependent Claim
77 words
In a method for producing an amino acid having a protected guanidino group or a peptide containing the residue of an amino acid having a protected guanidino group which comprises reacting an amino acid or peptide containing a guanidino group with a reactive derivative of a compound capable of introducing the protective grouping into the guanidino group the improvement according to which the reactive derivative is a reactive derivative of lower alkoxybenzenesulfonic acid or tri-lower alkylbenzenesulfonic acid.
Claim 18
Dependent Claim
77 words
In a method for producing an amino acid having a protected guanidino group or a peptide containing the residue of an amino acid having a protected guanidino group which comprises reacting an amino acid or peptide containing a guanidino group with a reactive derivative of a compound capable of introducing the protective grouping into the guanidino group the improvement according to which the reactive derivative is a reactive derivative of lower alkoxybenzenesulfonic acid or tri-lower alkylbenzenesulfonic acid.
Claim 19
Dependent Claim
39 words
A method according to claim 16 wherein the protective grouping introduced into the guanidino group is subsequently removed by reacting the amino acid or a peptide containing the protected guanidino group with lower alkyl sulfonic acid or halogenosulfonic acid.
References Cited (Backward Citations)
US3960830A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1979-12-14 | 1980-06-14 | 1980-12-14 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-12-14 | 1984-06-14 | 1984-12-14 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-12-14 | 1988-06-14 | 1988-12-14 | $7700.00 | Window Closed / Lapsed |