DE2047413C3 - Verfahren zur Herstellung von Peptiden in homogener Phase - Google Patents
Verfahren zur Herstellung von Peptiden in homogener PhaseInfo
- Publication number
- DE2047413C3 DE2047413C3 DE2047413A DE2047413A DE2047413C3 DE 2047413 C3 DE2047413 C3 DE 2047413C3 DE 2047413 A DE2047413 A DE 2047413A DE 2047413 A DE2047413 A DE 2047413A DE 2047413 C3 DE2047413 C3 DE 2047413C3
- Authority
- DE
- Germany
- Prior art keywords
- päg
- vai
- giy
- amino acid
- coupling
- 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.)
- Expired
Links
- 108090000765 processed proteins & peptides Proteins 0.000 title claims description 18
- 238000000034 method Methods 0.000 title claims description 13
- 102000004196 processed proteins & peptides Human genes 0.000 title claims description 9
- 230000008569 process Effects 0.000 title claims description 6
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- 238000010168 coupling process Methods 0.000 claims description 14
- 238000005859 coupling reaction Methods 0.000 claims description 14
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical group NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims description 13
- 230000008878 coupling Effects 0.000 claims description 12
- 210000004899 c-terminal region Anatomy 0.000 claims description 9
- 239000003153 chemical reaction reagent Substances 0.000 claims description 9
- 229920001223 polyethylene glycol Polymers 0.000 claims description 9
- 238000000502 dialysis Methods 0.000 claims description 4
- 239000012528 membrane Substances 0.000 claims description 4
- 238000005374 membrane filtration Methods 0.000 claims description 4
- 230000032050 esterification Effects 0.000 claims description 2
- 238000005886 esterification reaction Methods 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 36
- 150000001413 amino acids Chemical class 0.000 description 30
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 238000004458 analytical method Methods 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- 239000000706 filtrate Substances 0.000 description 8
- 238000000926 separation method Methods 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 6
- 229960000583 acetic acid Drugs 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 239000012071 phase Substances 0.000 description 6
- 238000000108 ultra-filtration Methods 0.000 description 6
- 239000002202 Polyethylene glycol Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 238000010647 peptide synthesis reaction Methods 0.000 description 5
- -1 tert-butyloxycarbonyl-amino Chemical group 0.000 description 5
- ODHCTXKNWHHXJC-VKHMYHEASA-N 5-oxo-L-proline Chemical compound OC(=O)[C@@H]1CCC(=O)N1 ODHCTXKNWHHXJC-VKHMYHEASA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 125000006239 protecting group Chemical group 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- WORJRXHJTUTINR-UHFFFAOYSA-N 1,4-dioxane;hydron;chloride Chemical compound Cl.C1COCCO1 WORJRXHJTUTINR-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 239000004793 Polystyrene Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- 108010085325 histidylproline Proteins 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 229920002223 polystyrene Polymers 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- 230000007717 exclusion Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000011068 loading method Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- XNSAINXGIQZQOO-UHFFFAOYSA-N n-[1-(2-carbamoylpyrrolidin-1-yl)-3-(1h-imidazol-5-yl)-1-oxopropan-2-yl]-5-oxopyrrolidine-2-carboxamide Chemical compound NC(=O)C1CCCN1C(=O)C(NC(=O)C1NC(=O)CC1)CC1=CN=CN1 XNSAINXGIQZQOO-UHFFFAOYSA-N 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- JXGVXCZADZNAMJ-NSHDSACASA-N (2s)-1-phenylmethoxycarbonylpyrrolidine-2-carboxylic acid Chemical compound OC(=O)[C@@H]1CCCN1C(=O)OCC1=CC=CC=C1 JXGVXCZADZNAMJ-NSHDSACASA-N 0.000 description 1
- YOETUEMZNOLGDB-UHFFFAOYSA-N 2-methylpropyl carbonochloridate Chemical compound CC(C)COC(Cl)=O YOETUEMZNOLGDB-UHFFFAOYSA-N 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- 102100029880 Glycodelin Human genes 0.000 description 1
- 101000585553 Homo sapiens Glycodelin Proteins 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 description 1
- MDXGYYOJGPFFJL-QMMMGPOBSA-N N(alpha)-t-butoxycarbonyl-L-leucine Chemical compound CC(C)C[C@@H](C(O)=O)NC(=O)OC(C)(C)C MDXGYYOJGPFFJL-QMMMGPOBSA-N 0.000 description 1
- NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical class ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Natural products CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 238000007098 aminolysis reaction Methods 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000029087 digestion Effects 0.000 description 1
- 238000007720 emulsion polymerization reaction Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- MHYCRLGKOZWVEF-UHFFFAOYSA-N ethyl acetate;hydrate Chemical compound O.CCOC(C)=O MHYCRLGKOZWVEF-UHFFFAOYSA-N 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- OWFXIOWLTKNBAP-UHFFFAOYSA-N isoamyl nitrite Chemical compound CC(C)CCON=O OWFXIOWLTKNBAP-UHFFFAOYSA-N 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229910000069 nitrogen hydride Inorganic materials 0.000 description 1
- 238000010979 pH adjustment Methods 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- NMHMNPHRMNGLLB-UHFFFAOYSA-N phloretic acid Chemical compound OC(=O)CCC1=CC=C(O)C=C1 NMHMNPHRMNGLLB-UHFFFAOYSA-N 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000012465 retentate Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 238000003836 solid-state method Methods 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
- 239000004474 valine Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 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
- C07K1/042—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length on carriers characterised by the nature of the carrier
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/10—Tetrapeptides
- C07K5/1002—Tetrapeptides with the first amino acid being neutral
- C07K5/1005—Tetrapeptides with the first amino acid being neutral and aliphatic
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Genetics & Genomics (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Life Sciences & Earth Sciences (AREA)
- Analytical Chemistry (AREA)
- Peptides Or Proteins (AREA)
- Separation Using Semi-Permeable Membranes (AREA)
Priority Applications (11)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2047413A DE2047413C3 (de) | 1970-09-26 | 1970-09-26 | Verfahren zur Herstellung von Peptiden in homogener Phase |
| CH1309971A CH567458A5 (enExample) | 1970-09-26 | 1971-09-07 | |
| IL37698A IL37698A (en) | 1970-09-26 | 1971-09-13 | Process for the manufacture of peptides |
| US00181609A US3772264A (en) | 1970-09-26 | 1971-09-17 | Homogenous peptide synthesis |
| NL7113179A NL7113179A (enExample) | 1970-09-26 | 1971-09-24 | |
| FR7134440A FR2108520A5 (enExample) | 1970-09-26 | 1971-09-24 | |
| BE773013A BE773013A (fr) | 1970-09-26 | 1971-09-24 | Procede pour la preparation de peptides |
| CA123,614A CA1000271A (en) | 1970-09-26 | 1971-09-24 | Process for the manufacture of peptides |
| SU1700240A SU454736A3 (ru) | 1970-09-26 | 1971-09-24 | Способ получени пептидов |
| SE7112135A SE398347B (sv) | 1970-09-26 | 1971-09-24 | Sett att framstella peptider genom koppling av en aminosyra med ytterligare aminosyror i homogen fas |
| GB4470171A GB1310656A (en) | 1970-09-26 | 1971-09-24 | Process for the manufacture of peptides |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2047413A DE2047413C3 (de) | 1970-09-26 | 1970-09-26 | Verfahren zur Herstellung von Peptiden in homogener Phase |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2047413A1 DE2047413A1 (de) | 1972-03-30 |
| DE2047413B2 DE2047413B2 (de) | 1979-09-06 |
| DE2047413C3 true DE2047413C3 (de) | 1980-05-29 |
Family
ID=5783460
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2047413A Expired DE2047413C3 (de) | 1970-09-26 | 1970-09-26 | Verfahren zur Herstellung von Peptiden in homogener Phase |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US3772264A (enExample) |
| BE (1) | BE773013A (enExample) |
| CA (1) | CA1000271A (enExample) |
| CH (1) | CH567458A5 (enExample) |
| DE (1) | DE2047413C3 (enExample) |
| FR (1) | FR2108520A5 (enExample) |
| GB (1) | GB1310656A (enExample) |
| IL (1) | IL37698A (enExample) |
| NL (1) | NL7113179A (enExample) |
| SE (1) | SE398347B (enExample) |
| SU (1) | SU454736A3 (enExample) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5183B2 (enExample) * | 1973-03-07 | 1976-01-05 | ||
| FR2419278A1 (fr) * | 1978-03-10 | 1979-10-05 | Pierce Chemical Co | Procede de synthese de chaines peptidiques |
| DE2930542A1 (de) * | 1979-07-27 | 1981-02-12 | Hoechst Ag | Neue insulinderivate und verfahren zu ihrer herstellung |
| DK608589D0 (da) * | 1989-12-01 | 1989-12-01 | Holm Arne | Kemisk fremgangsmaade |
| US5824784A (en) * | 1994-10-12 | 1998-10-20 | Amgen Inc. | N-terminally chemically modified protein compositions and methods |
| GB0814519D0 (en) | 2008-08-08 | 2008-09-17 | Imp Innovations Ltd | Process |
| GB0820865D0 (en) * | 2008-11-14 | 2008-12-24 | Membrane Extraction Tech Ltd | Degradable supports for tide synthesis |
| GB201413954D0 (en) | 2014-08-06 | 2014-09-17 | Imp Innovations Ltd | Process for preparing polymers |
-
1970
- 1970-09-26 DE DE2047413A patent/DE2047413C3/de not_active Expired
-
1971
- 1971-09-07 CH CH1309971A patent/CH567458A5/xx not_active IP Right Cessation
- 1971-09-13 IL IL37698A patent/IL37698A/xx unknown
- 1971-09-17 US US00181609A patent/US3772264A/en not_active Expired - Lifetime
- 1971-09-24 BE BE773013A patent/BE773013A/xx unknown
- 1971-09-24 GB GB4470171A patent/GB1310656A/en not_active Expired
- 1971-09-24 NL NL7113179A patent/NL7113179A/xx not_active Application Discontinuation
- 1971-09-24 FR FR7134440A patent/FR2108520A5/fr not_active Expired
- 1971-09-24 CA CA123,614A patent/CA1000271A/en not_active Expired
- 1971-09-24 SE SE7112135A patent/SE398347B/xx unknown
- 1971-09-24 SU SU1700240A patent/SU454736A3/ru active
Also Published As
| Publication number | Publication date |
|---|---|
| DE2047413A1 (de) | 1972-03-30 |
| FR2108520A5 (enExample) | 1972-05-19 |
| SU454736A3 (ru) | 1974-12-25 |
| DE2047413B2 (de) | 1979-09-06 |
| CH567458A5 (enExample) | 1975-10-15 |
| NL7113179A (enExample) | 1972-03-28 |
| GB1310656A (en) | 1973-03-21 |
| CA1000271A (en) | 1976-11-23 |
| IL37698A0 (en) | 1971-11-29 |
| IL37698A (en) | 1975-04-25 |
| SE398347B (sv) | 1977-12-19 |
| BE773013A (fr) | 1972-03-24 |
| US3772264A (en) | 1973-11-13 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| 8339 | Ceased/non-payment of the annual fee |