Patent US4138394A successfully refreshed from Google Patents.
US4138394A
Expired / Lapsed
US
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Peptide derivatives and a method of measuring collagenase activity
Assignee: Ajinomoto Co Inc
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Filing: 1977-01-21
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Granted: 1979-02-06
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Expires: 1997-01-21
Abstract
Abstract Peptide derivatives are obtained by eliminating the masking groups from masked peptide derivatives in which the guanidino group of an arginine residue and the carboxyl group of the arginine residue are masked. The guanidino group can be masked, for example, with a tosyl, nitro or benzyloxycarbonyl group, and the carboxyl group can be masked by converting it to an ester group, for example, a benzyl or t-butyl ester group. The masking groups can be eliminated using hydrogen fluoride, for example.
Inventors
- 👤 Shumpei Sakakibara
- 👤 Yutaka Nagai
- 👤 Kenji Fujiwara
- 👤 Takahiro Sakai
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-07 11:51
CPC Classifications
C; C07; C07K; C07K7/00; C07K7/04; C07K7/06; C07K14/00; C07K14/435; C07K14/78; C07K5/00; C07K5/04; C07K5/08; C07K5/0802; C07K5/0804; C07K5/0808; Y; Y10; Y10S; Y10S930/00; Y10S930/01; Y10S930/28
Claims Analysis
Total Claims: 17
Claim 1
Independent Claim
73 words
A peptide derivative having the structure A-Pro-B-Gly-C-Ala-Gly-E or A-b-gly-C-Ala-Gly-E where A is a hydrophobic, and neutral or acidic chromophore selected from the group consisting of 2, 4-dinitrophenyl, 5-dimethyl-amino-1-naphthalenesulfonyl, p-phenylazobenzyloxycarbonyl, p-nitrobenzyloxycarbonyl, p-(4-hydroxy-1-naphthylazo)benzenesulfonyl and p-phenylazobenzoyl, B is a residue of an alpha-amino acid having up to 15 carbon atoms occurring in protein, C is Ile or Leu, E is Gln-D-Arg-OH- or D-Arg-OH, and all amino acid residues except for Gly are L-configuration unless otherwise stated.
Claim 2
Dependent Claim
73 words
A peptide derivative having the structure A-Pro-B-Gly-C-Ala-Gly-E or A-b-gly-C-Ala-Gly-E where A is a hydrophobic, and neutral or acidic chromophore selected from the group consisting of 2, 4-dinitrophenyl, 5-dimethyl-amino-1-naphthalenesulfonyl, p-phenylazobenzyloxycarbonyl, p-nitrobenzyloxycarbonyl, p-(4-hydroxy-1-naphthylazo)benzenesulfonyl and p-phenylazobenzoyl, B is a residue of an alpha-amino acid having up to 15 carbon atoms occurring in protein, C is Ile or Leu, E is Gln-D-Arg-OH- or D-Arg-OH, and all amino acid residues except for Gly are L-configuration unless otherwise stated.
Claim 3
Dependent Claim
41 words
A derivative according to claim 1 wherein said B is a residue of an alpha-amino acid selected from the group consisting of glycine, alanine, valine, leucine, serine, threonine, proline, phenylalanine, tyrosine, tryptophane, lysine, arginine, aspartic acid, asparagine, glutamic acid and glutamine.
Claim 4
Dependent Claim
18 words
A derivative according to claim 1, wherein said B is a residue of alanine, proline, leucine or glutamine.
Claim 5
Dependent Claim
14 words
A derivative according to claim 1, wherein said A is 2,4-dinitrophenyl, p-(4-hydroxy-1-naphthylazo)-benzenesulfonyl, or p-phenylazobenzoyl.
Claim 6
Dependent Claim
5 words
2,4-Dinitrophenyl-Pro-Gln-Gly-Ile-Ala-Gly-Gln-D-Arg-OH according to claim 1.
Claim 7
Dependent Claim
5 words
2,4-Dinitrophenyl-Pro-Gln-Gly-Ile-Ala-Gly-D-Arg-OH according to claim 1.
Claim 8
Dependent Claim
5 words
2,4-Dinitrophenyl-Pro-Gln-Gly-Leu-Ala-Gly-Gln-D-Arg-OH according to claim 1.
Claim 9
Dependent Claim
5 words
2,4-Dinitrophenyl-Pro-Ala-Gly-Ile-Ala-Gly-Gln-D-Arg-OH according to claim 1.
Claim 10
Dependent Claim
5 words
2,4-Dinitrophenyl-Pro-Ala-Gly-Leu-Ala-Gly-Gln-D-Arg-OH according to claim 1.
Claim 11
Dependent Claim
5 words
2,4-Dinitrophenyl-Pro-Leu-Gly-Ile-Ala-Gly-Gln-D-Arg-OH according to claim 1.
Claim 12
Dependent Claim
5 words
2,4-Dinitrophenyl-Pro-Pro-Gly-Ile-Ala-Gly-Gln-D-Arg-OH according to claim 1.
Claim 13
Dependent Claim
5 words
p-(4-Hydroxy-1-naphthylazo)-benzenesulfonyl-Pro-Gln-Gly-Ile-Ala-Gly-Gln-D-Arg-OH according to claim 1.
Claim 14
Dependent Claim
5 words
p-phenylazobenzoyl-Pro-Gln-Gly-Ile-Ala-Gly-Gln-D-Arg-OH according to claim 1.
Claim 15
Dependent Claim
5 words
2,4-Dinitrophenyl-Gln-Gly-Ile-Ala-Gly-Gln-D-Arg-OH according to claim 1.
Claim 16
Dependent Claim
5 words
2,4-Dinitrophenyl-Ala-Gly-Ile-Ala-Gly-Gln-D-Arg-OH according to claim 1.
Claim 17
Dependent Claim
14 words
A derivative according to claim 3, wherein said A is 2,4-dinitrophenyl, p-(4-hydroxy-1-naphthylazo)-benzenesulfonyl, or p-phenylazobenzoyl.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1982-02-05 | 1982-08-07 | 1983-02-06 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1986-02-05 | 1986-08-07 | 1987-02-06 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1990-02-05 | 1990-08-07 | 1991-02-06 | $7700.00 | Window Closed / Lapsed |