US4041023A
Expired / Lapsed
US
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Labelled peptides
Assignee: Hoffmann La Roche Inc
•
Filing: 1976-04-14
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Granted: 1977-08-09
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Expires: 1996-04-14
Abstract
Abstract Radiolabelled and isotopically labelled peptides are prepared in a convenient and efficient manner by catalytically tritiating or deuterating an analog of the desired peptide containing one or more amino acid residues having an ethylenic type unsaturated bond therein. Preferred amino acid residues for this purpose include 3,4-dehydroproline (Δ 3 -proline) and trans-4,5-dehydrolysine (Δ 4 -lysine).
Inventors
- 👤 Arthur Martin Felix
- 👤 Arnold Alvin Liebman
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-23 22:34
CPC Classifications
C; C07; C07K; C07K5/00; C07K5/04; C07K5/08; C07K5/0821; C07K7/00; C07K7/04; C07K7/18
Claims Analysis
Total Claims: 25
Claim 1
Independent Claim
55 words
An improved process for preparing a non-randomized deuterated or tritiated amino acid or peptide product which process comprises treating respectively an ethylenically unsaturated amino acid or a peptide analogous to said peptide product, said analogous peptide containing at least one ethylenically unsaturated amino acid with deuterium or tritium in the presence of palladium oxide catalyst.
Claim 2
Dependent Claim
55 words
An improved process for preparing a non-randomized deuterated or tritiated amino acid or peptide product which process comprises treating respectively an ethylenically unsaturated amino acid or a peptide analogous to said peptide product, said analogous peptide containing at least one ethylenically unsaturated amino acid with deuterium or tritium in the presence of palladium oxide catalyst.
Claim 3
Dependent Claim
21 words
The process of claim 1 wherein said treatment with deuterium or tritium is carried out in absolute C 1-4 alkanol solvent.
Claim 4
Dependent Claim
12 words
The process of claim 2 wherein said C 1-4 alkanol is methanol.
Claim 5
Dependent Claim
21 words
The process of claim 1 wherein the ethylenically unsaturated amino acid in said analogous peptide is 3,4-dehydroproline or an enantiomer thereof.
Claim 6
Dependent Claim
17 words
The process of claim 4 wherein said analogous peptide is L-pyro-glutamyl-L-histidyl-L-3,4-dehydroprolinamide and the product peptide is L-pyroglutamyl-L-histidyl-L-3,4-dideuteroprolinamide.
Claim 7
Dependent Claim
17 words
The process of claim 4 wherein said analogous peptide is L-pyro-glutamyl-L-histidyl-L-3,4-dehydroprolinamide and the product peptide is L-pyroglutamyl-L-histidyl-L-3,4-ditritioprolinamide.
Claim 8
Dependent Claim
18 words
The process of claim 4 wherein said analogous peptide is L-3,4dehydroprolyl-L-leucylglycinamide and the product peptide is L-3,4-dideutero-prolyl-L-leucylglycinamide. prolyl-L-leucylglycinamide.
Claim 9
Dependent Claim
17 words
The process of claim 4 wherein said analogous peptide is L-3,4-dehydroprolyl-L-leucylglycinamide and the product peptide is L-3,4-ditritioprolyl-L-leucylglycinamide.
Claim 10
Dependent Claim
17 words
The process of claim 4 wherein said analogous peptide is L-glutamyl-L-prolyl-L-3,4-dehydroprolyl-glycyl-L-phenylalaninamide and the product peptide is L-glutamyl-L-prolyl-L-3,4-dideuteroprolyl-glycl-L-phenylalaninamide.
Claim 11
Dependent Claim
23 words
The process of claim 4 wherein said analogous peptide is (Δ 3 -Pro 3 )-bradykinin and the peptide product is 3,4-dideutero-Pro 3 -bradykinin.
Claim 12
Dependent Claim
22 words
The process of claim 1 wherein said ethylenically unsaturated amino acid is Δ 3 -proline and the amino acid produced is 3,4-dideuteroproline.
Claim 13
Dependent Claim
22 words
The process of claim 1 wherein said ethylenically unsaturated amino acid is Δ 3 -proline and the amino acid produced is 3,4-ditritioproline.
Claim 14
Dependent Claim
1 words
L-pyroglutamyl-L-histidyl-L-3,4-dideuteroprolinamide.
Claim 15
Dependent Claim
1 words
L-pyroglutamyl-L-histidyl-L-3,4-dideuteroprolinamide.
Claim 16
Dependent Claim
1 words
L-pyroglutamyl-L-histidyl-L-3,4-ditritioprolinamide.
Claim 17
Dependent Claim
1 words
L-pyroglutamyl-L-histidyl-L-3,4-ditritioprolinamide.
Claim 18
Dependent Claim
1 words
L-3,4-dideuteroprolyl-L-leucylglycinamide.
Claim 19
Dependent Claim
1 words
L-3,4-dideuteroprolyl-L-leucylglycinamide.
Claim 20
Dependent Claim
1 words
L-3,4-ditritioprolyl-L-leucylglycinamide.
Claim 21
Dependent Claim
1 words
L-3,4-ditritioprolyl-L-leucylglycinamide.
Claim 22
Dependent Claim
3 words
3,4-dideutero-Pro 3 -bradykinin.
Claim 23
Dependent Claim
3 words
3,4-dideutero-Pro 3 -bradykinin.
Claim 24
Dependent Claim
3 words
3,4-ditritio-Pro 3 -bradykinin.
Claim 25
Dependent Claim
3 words
3,4-ditritio-Pro 3 -bradykinin.
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) | 1980-08-08 | 1981-02-07 | 1981-08-09 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-08-08 | 1985-02-07 | 1985-08-09 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-08-08 | 1989-02-07 | 1989-08-09 | $7700.00 | Window Closed / Lapsed |