CA2050216A1 - Process for the preparation of peptides by solid-phase synthesis - Google Patents
Process for the preparation of peptides by solid-phase synthesisInfo
- Publication number
- CA2050216A1 CA2050216A1 CA002050216A CA2050216A CA2050216A1 CA 2050216 A1 CA2050216 A1 CA 2050216A1 CA 002050216 A CA002050216 A CA 002050216A CA 2050216 A CA2050216 A CA 2050216A CA 2050216 A1 CA2050216 A1 CA 2050216A1
- Authority
- CA
- Canada
- Prior art keywords
- converting
- appropriate
- peptides
- amino acid
- preparation
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 108090000765 processed proteins & peptides Proteins 0.000 title abstract 4
- 238000000034 method Methods 0.000 title abstract 3
- 238000002360 preparation method Methods 0.000 title abstract 2
- 102000004196 processed proteins & peptides Human genes 0.000 title abstract 2
- 238000010532 solid phase synthesis reaction Methods 0.000 title 1
- 239000002253 acid Substances 0.000 abstract 2
- 125000006239 protecting group Chemical group 0.000 abstract 2
- 239000011347 resin Substances 0.000 abstract 2
- 229920005989 resin Polymers 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- 125000006850 spacer group Chemical group 0.000 abstract 2
- 150000007513 acids Chemical class 0.000 abstract 1
- 230000010933 acylation Effects 0.000 abstract 1
- 238000005917 acylation reaction Methods 0.000 abstract 1
- 150000001413 amino acids Chemical class 0.000 abstract 1
- 210000004899 c-terminal region Anatomy 0.000 abstract 1
- 230000008878 coupling Effects 0.000 abstract 1
- 238000010168 coupling process Methods 0.000 abstract 1
- 238000005859 coupling reaction Methods 0.000 abstract 1
- 150000004675 formic acid derivatives Chemical class 0.000 abstract 1
- 125000001841 imino group Chemical group [H]N=* 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 230000002194 synthesizing effect Effects 0.000 abstract 1
Classifications
-
- 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
- C07K1/04—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length on carriers
-
- 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
- C07K1/06—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length using protecting groups or activating agents
-
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Analytical Chemistry (AREA)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Abstract
A process for the preparation of peptides of the formula (X)n-A-NH2 in which X is a natural or unnatural amino acid, aza-amino acid or imino acid, n is an integer from 1 to 50, preferably 1 to 30, and A is an aza-amino acid, and the physiologically tolerated salts thereof is described. Said process comprises the steps of converting a spacer into a form which is capable of acylation, reacting the latter with a suitable formic acid derivative and subsequently with an appropriate amino hydrazide, where appropriate, converting the protective group into a protective group which is base-labile or labile to weak acids, coupling the spacer obtained in this way to a resin, synthesizing the required peptide stepwise from the C-terminal end, subsequently cleaving the peptide off the resin and, where appropriate, converting it into physiologically tolerated salts thereof.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP4027394.6 | 1990-08-30 | ||
| DE4027394 | 1990-08-30 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2050216A1 true CA2050216A1 (en) | 1992-03-01 |
| CA2050216C CA2050216C (en) | 2003-03-11 |
Family
ID=6413202
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002050216A Expired - Lifetime CA2050216C (en) | 1990-08-30 | 1991-08-29 | Process for the preparation of peptides by solid-phase synthesis |
Country Status (22)
| Country | Link |
|---|---|
| EP (1) | EP0475184B1 (en) |
| JP (1) | JP3177269B2 (en) |
| KR (1) | KR100203548B1 (en) |
| AU (1) | AU646488B2 (en) |
| CA (1) | CA2050216C (en) |
| CZ (1) | CZ282881B6 (en) |
| DE (1) | DE59104538D1 (en) |
| DK (1) | DK0475184T3 (en) |
| ES (1) | ES2069148T3 (en) |
| FI (1) | FI102380B1 (en) |
| GR (1) | GR3015359T3 (en) |
| HU (1) | HU208838B (en) |
| IE (1) | IE66524B1 (en) |
| IL (1) | IL99338A (en) |
| NO (1) | NO300216B1 (en) |
| NZ (1) | NZ239575A (en) |
| PL (1) | PL167504B1 (en) |
| PT (1) | PT98813B (en) |
| RU (1) | RU2036200C1 (en) |
| SK (1) | SK280319B6 (en) |
| TW (1) | TW295589B (en) |
| ZA (1) | ZA916848B (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5602231A (en) * | 1991-06-14 | 1997-02-11 | Zeneca Limited | Process for making peptides |
| US10450343B2 (en) | 2013-03-21 | 2019-10-22 | Sanofi-Aventis Deutschland Gmbh | Synthesis of cyclic imide containing peptide products |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9727123D0 (en) * | 1997-12-22 | 1998-02-25 | Int Centre Genetic Eng & Bio | Synthesis of diamines |
| ES2154590B1 (en) * | 1999-05-20 | 2001-11-01 | Lipotec Sa | SOLID PHASE SYNTHESIS PROCEDURE |
| KR101346886B1 (en) | 2005-01-21 | 2014-01-02 | 아스텍스 테라퓨틱스 리미티드 | Pharmaceutical compounds |
| WO2008044045A1 (en) | 2006-10-12 | 2008-04-17 | Astex Therapeutics Limited | Pharmaceutical combinations |
| US8916552B2 (en) | 2006-10-12 | 2014-12-23 | Astex Therapeutics Limited | Pharmaceutical combinations |
| HK1219477A1 (en) | 2013-03-21 | 2017-04-07 | Sanofi-Aventis Deutschland Gmbh | Synthesis of hydantoin containing peptide products |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2061714T3 (en) * | 1987-12-22 | 1994-12-16 | Hoechst Ag | UNSTABLE ANCHOR GROUPS AGAINST ACIDS FOR THE SYNTHESIS OF PEPTIDIC AMIDES THROUGH THE SOLID PHASE METHOD. |
-
1991
- 1991-08-17 TW TW080106522A patent/TW295589B/zh active
- 1991-08-27 DK DK91114332.9T patent/DK0475184T3/en active
- 1991-08-27 ES ES91114332T patent/ES2069148T3/en not_active Expired - Lifetime
- 1991-08-27 EP EP91114332A patent/EP0475184B1/en not_active Expired - Lifetime
- 1991-08-27 DE DE59104538T patent/DE59104538D1/en not_active Expired - Lifetime
- 1991-08-28 IL IL9933891A patent/IL99338A/en not_active IP Right Cessation
- 1991-08-28 FI FI914064A patent/FI102380B1/en not_active IP Right Cessation
- 1991-08-28 NZ NZ239575A patent/NZ239575A/en not_active IP Right Cessation
- 1991-08-29 ZA ZA916848A patent/ZA916848B/en unknown
- 1991-08-29 PT PT98813A patent/PT98813B/en not_active IP Right Cessation
- 1991-08-29 RU SU915001313A patent/RU2036200C1/en active
- 1991-08-29 NO NO913396A patent/NO300216B1/en not_active IP Right Cessation
- 1991-08-29 IE IE305191A patent/IE66524B1/en not_active IP Right Cessation
- 1991-08-29 CZ CS912666A patent/CZ282881B6/en not_active IP Right Cessation
- 1991-08-29 SK SK2666-91A patent/SK280319B6/en not_active IP Right Cessation
- 1991-08-29 KR KR1019910014992A patent/KR100203548B1/en not_active Expired - Lifetime
- 1991-08-29 PL PL91291561A patent/PL167504B1/en unknown
- 1991-08-29 CA CA002050216A patent/CA2050216C/en not_active Expired - Lifetime
- 1991-08-29 AU AU83402/91A patent/AU646488B2/en not_active Expired
- 1991-08-29 JP JP21852591A patent/JP3177269B2/en not_active Expired - Lifetime
- 1991-08-30 HU HU912825A patent/HU208838B/en unknown
-
1995
- 1995-03-10 GR GR950400517T patent/GR3015359T3/en unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5602231A (en) * | 1991-06-14 | 1997-02-11 | Zeneca Limited | Process for making peptides |
| US10450343B2 (en) | 2013-03-21 | 2019-10-22 | Sanofi-Aventis Deutschland Gmbh | Synthesis of cyclic imide containing peptide products |
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Vepřek et al. | Peptide and glycopeptide dendrimers. Part II | |
| EP1277762A3 (en) | Low allergenic protein variants | |
| Tuchscherer | Template assembled synthetic proteins: condensation of a multifunctional peptide to a topological template via chemoselective ligation | |
| AU1704092A (en) | Process for making peptides | |
| WO1988001173A1 (en) | Benzylthioether-linked solid support-bound thiol compounds and method for peptide synthesis | |
| US5869606A (en) | Amino acids peptides or derivatives thereof coupled to fats | |
| CA2050216A1 (en) | Process for the preparation of peptides by solid-phase synthesis | |
| CA2202390A1 (en) | Keratinocyte growth factor analogs | |
| Funakoshi et al. | Chemoselective one-step purification method for peptides synthesized by the solid-phase technique. | |
| WO2001062775A3 (en) | Novel antiarrhythmic peptides | |
| US5391711A (en) | Biotinylating reagent and purification process for synthesized peptide using thereof | |
| ATE153028T1 (en) | PEPTIDE SYNTHESIS IN A SOLID PHASE | |
| CA1174623A (en) | Process for preparing human insulin or b-30 esters thereof | |
| HU204071B (en) | Process for producing immune stimulant peptides and pharmaceutical compositions comprising same | |
| Ishii et al. | Silyl linker-based approach to the solid-phase synthesis of Fmoc glycopeptide thioesters | |
| US7420035B2 (en) | Purification of polypeptides | |
| JPH03503958A (en) | Method for producing calcitonin gene-related peptide | |
| Lang et al. | Chemoselectively addressable HCan building blocks in peptide synthesis: l‐homocanaline derivatives | |
| HU221619B1 (en) | Process for synthetise peptides and intermediates thereof | |
| EP0277561B1 (en) | New arginine derivative, process for the preparation thereof and its use in peptide synthesis | |
| CA2125636A1 (en) | Process for preparing an .alpha.-amino acid amide, useful for peptidic synthesis | |
| US20070111930A1 (en) | Process for preparing vapreotide | |
| GB9522302D0 (en) | Growth promoters | |
| WO1996012729A3 (en) | Method for peptide synthesis based on n-(n'-nitrosocarbamoyl)amino acids | |
| JPS58500739A (en) | Method for producing insulin derivatives |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKEX | Expiry |