US3960828A
Expired / Lapsed
US
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Catalytic hydrogenolysis of protected sulfur containing peptides
Assignee: United States Department of Health and Human Services
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Filing: 1974-03-20
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Granted: 1976-06-01
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Expires: 1994-03-20
Abstract
Abstract The use of catalytic hydrogenolysis to selectively deblock protected moieties in sulfur containing compounds has not been a practical process due to poisoning of the catalyst by the sulfur compound. It has now been found that catalytic hydrogenolysis of sulfur compounds can be successfully carried out by conducting the reaction in liquid ammonia as solvent.
Inventors
- 👤 Johannes Arnold Meienhofer
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-01 16:27
CPC Classifications
C; C07; C07K; C07K1/00; C07K1/12; C07K1/126; C07K5/00; C07K5/04; C07K5/10; C07K5/1002; C07K5/1005; C07K5/1013; Y; Y10; Y10S; Y10S930/00; Y10S930/01; Y10S930/15
Claims Analysis
Total Claims: 7
Claim 1
Independent Claim
54 words
A process for the catalytic hydrogenolysis of sulfur containing peptide compounds also containing a benzyloxycarbonyl protective group labile to hydrogenolysis and additionally containing one or more protective groups which are stable to hydrogenolysis which process comprises reacting said sulfur compounds with hydrogen in the presence of palladium catalyst in a liquid ammonia solvent medium.
Claim 2
Dependent Claim
54 words
A process for the catalytic hydrogenolysis of sulfur containing peptide compounds also containing a benzyloxycarbonyl protective group labile to hydrogenolysis and additionally containing one or more protective groups which are stable to hydrogenolysis which process comprises reacting said sulfur compounds with hydrogen in the presence of palladium catalyst in a liquid ammonia solvent medium.
Claim 3
Dependent Claim
26 words
The process of claim 1 wherein said sulfur containing peptides contain at least one residue of the group consisting of cysteine, homocysteine, methionine, penicillamine and thiazolidine.
Claim 4
Dependent Claim
26 words
The process of claim 1 wherein said stable protective group is selected from the group consisting of t-butyl ester, t-butyl ether, N-t-butyloxycarbonyl, N-p-toluenesulfonyl, S-benzyl and S-acetamidomethyl.
Claim 5
Dependent Claim
27 words
The process of claim 1 wherein the process is conducted in an open system and at a temperature in the range of from about -33 to -70°C.
Claim 6
Dependent Claim
25 words
The process of claim 1 wherein the process is conducted in a closed system, at elevated pressures and at a temperature of about room temperature.
Claim 7
Dependent Claim
16 words
The process of claim 1 wherein the said palladium is in the form of palladium black.
References Cited (Backward Citations)
No citation records indexed.
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1979-06-01 | 1979-12-01 | 1980-06-01 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-06-01 | 1983-12-01 | 1984-06-01 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-06-01 | 1987-12-01 | 1988-06-01 | $7700.00 | Window Closed / Lapsed |