GR1006759B - Improved chemical synthesis of human relaxin - Google Patents
Improved chemical synthesis of human relaxinInfo
- Publication number
- GR1006759B GR1006759B GR20080100815A GR20080100815A GR1006759B GR 1006759 B GR1006759 B GR 1006759B GR 20080100815 A GR20080100815 A GR 20080100815A GR 20080100815 A GR20080100815 A GR 20080100815A GR 1006759 B GR1006759 B GR 1006759B
- Authority
- GR
- Greece
- Prior art keywords
- relaxin
- chains
- improved chemical
- methionine
- methionine sulfoxide
- Prior art date
Links
- 238000003786 synthesis reaction Methods 0.000 title abstract 2
- BJRCFZKVYNDCJE-WBSNEMHCSA-N 99489-95-9 Chemical compound C([C@@H]1NC(=O)[C@H](CCCCN)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CO)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CCCCN)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@@H]2CSSC[C@@H](C(=O)N[C@H](C(N[C@@H](CC(C)C)C(=O)N[C@H](C(=O)NCC(=O)N2)[C@@H](C)CC)=O)CSSC[C@@H](C(NCC(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@H](C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](C)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@H](C(=O)N[C@@H](C)C(=O)N[C@H](C(=O)N[C@@H](CSSC[C@H](NC1=O)C(O)=O)C(=O)NCC(=O)N[C@@H](CCSC)C(=O)N[C@@H](CO)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CO)C(=O)N[C@@H](CC(C)C)C(O)=O)[C@@H](C)CC)[C@@H](C)CC)C(C)C)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCCN)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@@H](N)CCCCN)C(C)C)[C@@H](C)CC)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](C)NC(=O)[C@@H](NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H]1N(CCC1)C(=O)[C@@H](N)CCCNC(N)=N)C(C)C)C1=CC=C(O)C=C1 BJRCFZKVYNDCJE-WBSNEMHCSA-N 0.000 title 1
- 101001091094 Homo sapiens Prorelaxin H1 Proteins 0.000 abstract 5
- 101001091088 Homo sapiens Prorelaxin H2 Proteins 0.000 abstract 5
- 102100034945 Prorelaxin H1 Human genes 0.000 abstract 5
- 102100034949 Prorelaxin H2 Human genes 0.000 abstract 5
- QEFRNWWLZKMPFJ-ZXPFJRLXSA-N L-methionine (R)-S-oxide Chemical compound C[S@@](=O)CC[C@H]([NH3+])C([O-])=O QEFRNWWLZKMPFJ-ZXPFJRLXSA-N 0.000 abstract 3
- QEFRNWWLZKMPFJ-UHFFFAOYSA-N L-methionine sulphoxide Natural products CS(=O)CCC(N)C(O)=O QEFRNWWLZKMPFJ-UHFFFAOYSA-N 0.000 abstract 3
- 102000003743 Relaxin Human genes 0.000 abstract 2
- 108090000103 Relaxin Proteins 0.000 abstract 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 abstract 1
- 239000003638 chemical reducing agent Substances 0.000 abstract 1
- 229940088679 drug related substance Drugs 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 229930182817 methionine Natural products 0.000 abstract 1
- 125000001360 methionine group Chemical group N[C@@H](CCSC)C(=O)* 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- 150000003462 sulfoxides Chemical class 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- C07K14/435—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
- C07K14/575—Hormones
- C07K14/64—Relaxins
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- A61K38/16—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- A61K38/17—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
- A61K38/22—Hormones
- A61K38/2221—Relaxins
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- General Health & Medical Sciences (AREA)
- Endocrinology (AREA)
- Zoology (AREA)
- Molecular Biology (AREA)
- Biophysics (AREA)
- Biochemistry (AREA)
- Genetics & Genomics (AREA)
- Gastroenterology & Hepatology (AREA)
- Engineering & Computer Science (AREA)
- Toxicology (AREA)
- Analytical Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Immunology (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Abstract
In our invention are described improved chemical methods for producing the pharmaceutically active peptides Relaxin-1 and Relaxin-2 which are better suited as drug substances in comparison to recombinant derivatives. The key step of the syntheses isthe production of Relaxin B-chains containing methionine sulfoxide instead of methionine at position 24 for Relaxin 1 and at position 25 for Relaxin 2. That methionine sulfoxide containing B-chains are better soluble and allow the random combinationof the Relaxin A and B-chains to give methioninee sulfoxide containing Relaxin-1 and Relaxin-2 in high yield. The methionine sulfoxide containing Relaxin-1 and Relaxin-2 are reduced finally to the native Relaxin 1 and Relaxin 2 using ammonium iodideas the reducing agent.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GR20080100815A GR1006759B (en) | 2008-12-22 | 2008-12-22 | Improved chemical synthesis of human relaxin |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GR20080100815A GR1006759B (en) | 2008-12-22 | 2008-12-22 | Improved chemical synthesis of human relaxin |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GR1006759B true GR1006759B (en) | 2010-04-20 |
Family
ID=42245147
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GR20080100815A GR1006759B (en) | 2008-12-22 | 2008-12-22 | Improved chemical synthesis of human relaxin |
Country Status (1)
| Country | Link |
|---|---|
| GR (1) | GR1006759B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010140060A3 (en) * | 2009-06-01 | 2011-05-19 | Chemical & Biopharmaceutical Laboratories Of Patras S.A. | Relaxin peptide synthesis |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4656249A (en) * | 1982-06-10 | 1987-04-07 | Howard Florey Institute Of Experimental Physiology And Medicine | Peptides with relaxin activity |
| EP0251615A2 (en) * | 1986-06-23 | 1988-01-07 | Genentech, Inc. | Method of chain combination |
| US6200953B1 (en) * | 1995-06-07 | 2001-03-13 | Connetics Corporation | Relaxin analogs and derivatives compositions |
| WO2004113381A1 (en) * | 2003-06-20 | 2004-12-29 | Howard Florey Institute Of Experimental Physiology And Medicine | Relaxin superfamily peptide analogues |
-
2008
- 2008-12-22 GR GR20080100815A patent/GR1006759B/en active IP Right Grant
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4656249A (en) * | 1982-06-10 | 1987-04-07 | Howard Florey Institute Of Experimental Physiology And Medicine | Peptides with relaxin activity |
| EP0251615A2 (en) * | 1986-06-23 | 1988-01-07 | Genentech, Inc. | Method of chain combination |
| US6200953B1 (en) * | 1995-06-07 | 2001-03-13 | Connetics Corporation | Relaxin analogs and derivatives compositions |
| WO2004113381A1 (en) * | 2003-06-20 | 2004-12-29 | Howard Florey Institute Of Experimental Physiology And Medicine | Relaxin superfamily peptide analogues |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010140060A3 (en) * | 2009-06-01 | 2011-05-19 | Chemical & Biopharmaceutical Laboratories Of Patras S.A. | Relaxin peptide synthesis |
| CN102647996A (en) * | 2009-06-01 | 2012-08-22 | 帕特拉斯化学与生物制药实验室 | Relaxin peptide synthesis |
| US8785384B2 (en) | 2009-06-01 | 2014-07-22 | Chemical & Biopharmaceutical Laboratories of Patras | Peptide synthesis |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PG | Patent granted |