CH620671A5 - Process for the preparation of a peptide - Google Patents
Process for the preparation of a peptide Download PDFInfo
- Publication number
- CH620671A5 CH620671A5 CH1336376A CH1336376A CH620671A5 CH 620671 A5 CH620671 A5 CH 620671A5 CH 1336376 A CH1336376 A CH 1336376A CH 1336376 A CH1336376 A CH 1336376A CH 620671 A5 CH620671 A5 CH 620671A5
- Authority
- CH
- Switzerland
- Prior art keywords
- group
- acid
- amino acid
- proteinase
- water
- Prior art date
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- IPJUIRDNBFZGQN-SCZZXKLOSA-N (2s,3r)-3-hydroxy-2-(phenylmethoxycarbonylamino)butanoic acid Chemical compound C[C@@H](O)[C@@H](C(O)=O)NC(=O)OCC1=CC=CC=C1 IPJUIRDNBFZGQN-SCZZXKLOSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 235000001674 Agaricus brunnescens Nutrition 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- WYBVBIHNJWOLCJ-IUCAKERBSA-N Arg-Leu Chemical compound CC(C)C[C@@H](C(O)=O)NC(=O)[C@@H](N)CCCNC(N)=N WYBVBIHNJWOLCJ-IUCAKERBSA-N 0.000 description 1
- 108090000101 Asclepain Proteins 0.000 description 1
- DCXYFEDJOCDNAF-UHFFFAOYSA-N Asparagine Natural products OC(=O)C(N)CC(N)=O DCXYFEDJOCDNAF-UHFFFAOYSA-N 0.000 description 1
- 235000014469 Bacillus subtilis Nutrition 0.000 description 1
- 125000001433 C-terminal amino-acid group Chemical group 0.000 description 1
- 108010013369 Enteropeptidase Proteins 0.000 description 1
- 102100029727 Enteropeptidase Human genes 0.000 description 1
- 102000018389 Exopeptidases Human genes 0.000 description 1
- 108010091443 Exopeptidases Proteins 0.000 description 1
- 229930183217 Genin Natural products 0.000 description 1
- 241001245789 Goodea atripinnis Species 0.000 description 1
- 241000193159 Hathewaya histolytica Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 241000242768 Metridium Species 0.000 description 1
- UEQUQVLFIPOEMF-UHFFFAOYSA-N Mianserin Chemical compound C1C2=CC=CC=C2N2CCN(C)CC2C2=CC=CC=C21 UEQUQVLFIPOEMF-UHFFFAOYSA-N 0.000 description 1
- KUUUDPTUEOKITK-AWEZNQCLSA-N N-benzoyl-L-tyrosine Chemical compound C([C@@H](C(=O)O)NC(=O)C=1C=CC=CC=1)C1=CC=C(O)C=C1 KUUUDPTUEOKITK-AWEZNQCLSA-N 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium on carbon Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
- 102000007079 Peptide Fragments Human genes 0.000 description 1
- 108010033276 Peptide Fragments Proteins 0.000 description 1
- 102000015731 Peptide Hormones Human genes 0.000 description 1
- 108010038988 Peptide Hormones Proteins 0.000 description 1
- 241000219833 Phaseolus Species 0.000 description 1
- 101100008569 Rattus norvegicus Cst4 gene Proteins 0.000 description 1
- 101001091368 Rattus norvegicus Glandular kallikrein-7, submandibular/renal Proteins 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- 101000898773 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) Saccharopepsin Proteins 0.000 description 1
- 108090000787 Subtilisin Proteins 0.000 description 1
- 108010056079 Subtilisins Proteins 0.000 description 1
- 102000005158 Subtilisins Human genes 0.000 description 1
- 108090000190 Thrombin Proteins 0.000 description 1
- 108090000631 Trypsin Proteins 0.000 description 1
- 102000004142 Trypsin Human genes 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000004442 acylamino group Chemical group 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 108010051873 alkaline protease Proteins 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 235000009582 asparagine Nutrition 0.000 description 1
- 229960001230 asparagine Drugs 0.000 description 1
- 229960002319 barbital Drugs 0.000 description 1
- 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 108090001015 cancer procoagulant Proteins 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 229960002433 cysteine Drugs 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- MGHPNCMVUAKAIE-UHFFFAOYSA-N diphenylmethanamine Chemical group C=1C=CC=CC=1C(N)C1=CC=CC=C1 MGHPNCMVUAKAIE-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003248 enzyme activator Substances 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- MVEAAGBEUOMFRX-UHFFFAOYSA-N ethyl acetate;hydrochloride Chemical compound Cl.CCOC(C)=O MVEAAGBEUOMFRX-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- TYVBXJMXOIQEMZ-HNNXBMFYSA-N n-[(2s)-1-[(2-amino-2-oxoethyl)amino]-3-(4-hydroxyphenyl)-1-oxopropan-2-yl]benzamide Chemical compound C([C@@H](C(=O)NCC(=O)N)NC(=O)C=1C=CC=CC=1)C1=CC=C(O)C=C1 TYVBXJMXOIQEMZ-HNNXBMFYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229910000069 nitrogen hydride Inorganic materials 0.000 description 1
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 description 1
- 239000000813 peptide hormone Substances 0.000 description 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- 235000019419 proteases Nutrition 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 229960004072 thrombin Drugs 0.000 description 1
- 239000012588 trypsin Substances 0.000 description 1
- 150000003672 ureas Chemical class 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
- C07K1/02—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length in solution
-
- 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
- C07K5/06—Dipeptides
- C07K5/06086—Dipeptides with the first amino acid being basic
- C07K5/06095—Arg-amino acid
-
- 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
- C07K5/08—Tripeptides
- C07K5/0819—Tripeptides with the first amino acid being acidic
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P21/00—Preparation of peptides or proteins
- C12P21/02—Preparation of peptides or proteins having a known sequence of two or more amino acids, e.g. glutathione
-
- 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)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Medicinal Chemistry (AREA)
- Biophysics (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Engineering & Computer Science (AREA)
- Microbiology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biotechnology (AREA)
- Analytical Chemistry (AREA)
- Peptides Or Proteins (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP50126878A JPS5251093A (en) | 1975-10-23 | 1975-10-23 | Mthod of preparing peptides |
| JP50126876A JPS5251092A (en) | 1975-10-23 | 1975-10-23 | Method of preparing peptides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH620671A5 true CH620671A5 (en) | 1980-12-15 |
Family
ID=26462969
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1336376A CH620671A5 (en) | 1975-10-23 | 1976-10-22 | Process for the preparation of a peptide |
Country Status (7)
| Country | Link |
|---|---|
| CA (1) | CA1059938A (enExample) |
| CH (1) | CH620671A5 (enExample) |
| DE (1) | DE2647188C2 (enExample) |
| FR (1) | FR2328694A1 (enExample) |
| GB (1) | GB1533129A (enExample) |
| IT (1) | IT1077078B (enExample) |
| NL (2) | NL173979C (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0126009A1 (fr) * | 1983-05-16 | 1984-11-21 | Etablissement Public dit: CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE (CNRS) | Nouveaux dérivés de peptides, leur préparation et leur application comme inhibiteurs de l'élastase |
| EP0204374A3 (en) * | 1985-06-05 | 1988-07-13 | Eniricerche S.P.A. | Tripeptidic compounds having hypotensive activity |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5002872A (en) * | 1989-05-10 | 1991-03-26 | W. R. Grace & Co.-Conn. | Enzyme mediated coupling reactions |
-
1976
- 1976-10-15 GB GB42958/76A patent/GB1533129A/en not_active Expired
- 1976-10-19 DE DE2647188A patent/DE2647188C2/de not_active Expired
- 1976-10-22 CH CH1336376A patent/CH620671A5/de not_active IP Right Cessation
- 1976-10-22 CA CA263,981A patent/CA1059938A/en not_active Expired
- 1976-10-22 NL NLAANVRAGE7611698,A patent/NL173979C/xx not_active IP Right Cessation
- 1976-10-22 FR FR7631893A patent/FR2328694A1/fr active Granted
- 1976-10-22 IT IT28604/76A patent/IT1077078B/it active
-
1983
- 1983-03-29 NL NL8301093A patent/NL8301093A/nl active Search and Examination
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0126009A1 (fr) * | 1983-05-16 | 1984-11-21 | Etablissement Public dit: CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE (CNRS) | Nouveaux dérivés de peptides, leur préparation et leur application comme inhibiteurs de l'élastase |
| FR2546164A1 (fr) * | 1983-05-16 | 1984-11-23 | Centre Nat Rech Scient | Nouveaux derives de peptides, leur preparation et leur application comme inhibiteurs de l'elastase |
| EP0204374A3 (en) * | 1985-06-05 | 1988-07-13 | Eniricerche S.P.A. | Tripeptidic compounds having hypotensive activity |
Also Published As
| Publication number | Publication date |
|---|---|
| NL173979B (nl) | 1983-11-01 |
| DE2647188C2 (de) | 1983-03-24 |
| GB1533129A (en) | 1978-11-22 |
| IT1077078B (it) | 1985-04-27 |
| FR2328694B1 (enExample) | 1980-03-28 |
| NL173979C (nl) | 1984-04-02 |
| FR2328694A1 (fr) | 1977-05-20 |
| CA1059938A (en) | 1979-08-07 |
| NL7611698A (nl) | 1977-04-26 |
| DE2647188A1 (de) | 1977-04-28 |
| NL8301093A (nl) | 1983-08-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |