CA1040123A - Physiologically active peptide and its n-acyl derivatives and processes for producing thereof - Google Patents
Physiologically active peptide and its n-acyl derivatives and processes for producing thereofInfo
- Publication number
- CA1040123A CA1040123A CA221,066A CA221066A CA1040123A CA 1040123 A CA1040123 A CA 1040123A CA 221066 A CA221066 A CA 221066A CA 1040123 A CA1040123 A CA 1040123A
- Authority
- CA
- Canada
- Prior art keywords
- val
- ala
- atcc
- peptide
- acyl
- 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
- 238000000034 method Methods 0.000 title claims abstract description 90
- 108090000765 processed proteins & peptides Proteins 0.000 title claims abstract description 69
- 230000008569 process Effects 0.000 title claims abstract description 30
- KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Chemical compound CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 claims abstract description 31
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 22
- 125000003277 amino group Chemical group 0.000 claims abstract description 21
- 102000004196 processed proteins & peptides Human genes 0.000 claims abstract description 20
- 229960004295 valine Drugs 0.000 claims abstract description 19
- 241000024188 Andala Species 0.000 claims abstract description 18
- KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 claims abstract description 18
- 150000002148 esters Chemical group 0.000 claims abstract description 15
- 238000002360 preparation method Methods 0.000 claims abstract description 15
- DFVFTMTWCUHJBL-UHFFFAOYSA-N 4-azaniumyl-3-hydroxy-6-methylheptanoate Chemical compound CC(C)CC(N)C(O)CC(O)=O DFVFTMTWCUHJBL-UHFFFAOYSA-N 0.000 claims abstract description 14
- 150000003839 salts Chemical group 0.000 claims abstract description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 13
- 229960003767 alanine Drugs 0.000 claims abstract description 7
- 125000005843 halogen group Chemical group 0.000 claims abstract description 7
- 150000001768 cations Chemical group 0.000 claims abstract description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 5
- QNAYBMKLOCPYGJ-UHFFFAOYSA-N D-alpha-Ala Natural products CC([NH3+])C([O-])=O QNAYBMKLOCPYGJ-UHFFFAOYSA-N 0.000 claims abstract description 4
- QNAYBMKLOCPYGJ-UWTATZPHSA-N L-Alanine Natural products C[C@@H](N)C(O)=O QNAYBMKLOCPYGJ-UWTATZPHSA-N 0.000 claims abstract description 4
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 claims abstract description 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims abstract 2
- 230000000694 effects Effects 0.000 claims description 73
- 102000004190 Enzymes Human genes 0.000 claims description 60
- 108090000790 Enzymes Proteins 0.000 claims description 60
- -1 carboxylic acid halides Chemical class 0.000 claims description 50
- 244000005700 microbiome Species 0.000 claims description 27
- 239000000126 substance Substances 0.000 claims description 14
- 229940024606 amino acid Drugs 0.000 claims description 13
- 150000001413 amino acids Chemical class 0.000 claims description 13
- 230000010933 acylation Effects 0.000 claims description 12
- 238000005917 acylation reaction Methods 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 9
- 239000003795 chemical substances by application Substances 0.000 claims description 9
- 239000000758 substrate Substances 0.000 claims description 8
- 241001660259 Cereus <cactus> Species 0.000 claims description 7
- 241000589516 Pseudomonas Species 0.000 claims description 6
- 241000193830 Bacillus <bacterium> Species 0.000 claims description 5
- 102000035195 Peptidases Human genes 0.000 claims description 5
- 108091005804 Peptidases Proteins 0.000 claims description 5
- 241000778032 Aureobasidium caulivorum Species 0.000 claims description 4
- 150000008064 anhydrides Chemical class 0.000 claims description 4
- 235000019833 protease Nutrition 0.000 claims description 4
- ULGJWNIHLSLQPZ-UHFFFAOYSA-N 7-[(6,8-dichloro-1,2,3,4-tetrahydroacridin-9-yl)amino]-n-[2-(1h-indol-3-yl)ethyl]heptanamide Chemical compound C1CCCC2=NC3=CC(Cl)=CC(Cl)=C3C(NCCCCCCC(=O)NCCC=3C4=CC=CC=C4NC=3)=C21 ULGJWNIHLSLQPZ-UHFFFAOYSA-N 0.000 claims description 3
- 241000186320 Cellulomonas fimi Species 0.000 claims description 3
- 241000588724 Escherichia coli Species 0.000 claims description 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 3
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 claims description 3
- 125000002714 alpha-linolenoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])/C([H])=C([H])\C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 108010003977 aminoacylase I Proteins 0.000 claims description 3
- 125000001124 arachidoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 3
- 125000001721 carboxyacetyl group Chemical group 0.000 claims description 3
- 125000000400 lauroyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000002669 linoleoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000001419 myristoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000002801 octanoyl group Chemical group C(CCCCCCC)(=O)* 0.000 claims description 3
- 125000002811 oleoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000003431 oxalo group Chemical group 0.000 claims description 3
- 125000001312 palmitoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000000612 phthaloyl group Chemical group C(C=1C(C(=O)*)=CC=CC1)(=O)* 0.000 claims description 3
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000003696 stearoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 241000589212 Acetobacter pasteurianus Species 0.000 claims description 2
- 241000588813 Alcaligenes faecalis Species 0.000 claims description 2
- 241001480643 Colletotrichum sp. Species 0.000 claims description 2
- 241000191948 Kocuria rosea Species 0.000 claims description 2
- 241001495426 Macrophomina phaseolina Species 0.000 claims description 2
- 241000586779 Protaminobacter Species 0.000 claims description 2
- 241000158504 Rhodococcus hoagii Species 0.000 claims description 2
- 241000191963 Staphylococcus epidermidis Species 0.000 claims description 2
- 229940005347 alcaligenes faecalis Drugs 0.000 claims description 2
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 claims description 2
- 150000003566 thiocarboxylic acids Chemical class 0.000 claims description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 2
- 230000000813 microbial effect Effects 0.000 claims 2
- 241000607528 Aeromonas hydrophila Species 0.000 claims 1
- 241000589155 Agrobacterium tumefaciens Species 0.000 claims 1
- 241000194107 Bacillus megaterium Species 0.000 claims 1
- 241001274890 Boeremia exigua Species 0.000 claims 1
- 241000193171 Clostridium butyricum Species 0.000 claims 1
- 241000186145 Corynebacterium ammoniagenes Species 0.000 claims 1
- 241000194032 Enterococcus faecalis Species 0.000 claims 1
- 241001149959 Fusarium sp. Species 0.000 claims 1
- 241000588915 Klebsiella aerogenes Species 0.000 claims 1
- 240000001929 Lactobacillus brevis Species 0.000 claims 1
- 235000013957 Lactobacillus brevis Nutrition 0.000 claims 1
- 241000192132 Leuconostoc Species 0.000 claims 1
- 241001467566 Microbacterium lacticum Species 0.000 claims 1
- 241000191938 Micrococcus luteus Species 0.000 claims 1
- 241000242366 Microcyclus Species 0.000 claims 1
- 241001524178 Paenarthrobacter ureafaciens Species 0.000 claims 1
- 241000186334 Propionibacterium freudenreichii subsp. shermanii Species 0.000 claims 1
- 241000684075 Rhizoctonia sp. Species 0.000 claims 1
- 241000266363 Stemphylium sarciniforme Species 0.000 claims 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 229940092559 enterobacter aerogenes Drugs 0.000 claims 1
- 125000000268 heptanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 229940088598 enzyme Drugs 0.000 description 55
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
- 150000001875 compounds Chemical class 0.000 description 40
- 210000004027 cell Anatomy 0.000 description 36
- 239000002609 medium Substances 0.000 description 36
- 238000002474 experimental method Methods 0.000 description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
- 239000000243 solution Substances 0.000 description 24
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- 238000006731 degradation reaction Methods 0.000 description 22
- 239000000203 mixture Substances 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 20
- 239000000284 extract Substances 0.000 description 18
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 16
- 125000002252 acyl group Chemical group 0.000 description 16
- 238000003756 stirring Methods 0.000 description 16
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- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
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- 238000006460 hydrolysis reaction Methods 0.000 description 12
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 12
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 12
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- 239000004474 valine Substances 0.000 description 11
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- GWYFCOCPABKNJV-UHFFFAOYSA-N beta-methyl-butyric acid Natural products CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 8
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- 239000005720 sucrose Substances 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 239000011573 trace mineral Substances 0.000 description 1
- 235000013619 trace mineral Nutrition 0.000 description 1
- 238000000108 ultra-filtration Methods 0.000 description 1
- 229940005605 valeric acid Drugs 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000015099 wheat brans Nutrition 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- JLYXXMFPNIAWKQ-UHFFFAOYSA-N γ Benzene hexachloride Chemical compound ClC1C(Cl)C(Cl)C(Cl)C(Cl)C1Cl JLYXXMFPNIAWKQ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/02—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link
- C07K5/0205—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link containing the structure -NH-(X)3-C(=0)-, e.g. statine or derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
- C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
- C12N9/14—Hydrolases (3)
- C12N9/48—Hydrolases (3) acting on peptide bonds (3.4)
- C12N9/50—Proteinases, e.g. Endopeptidases (3.4.21-3.4.25)
- C12N9/52—Proteinases, e.g. Endopeptidases (3.4.21-3.4.25) derived from bacteria or Archaea
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
- C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
- C12N9/14—Hydrolases (3)
- C12N9/48—Hydrolases (3) acting on peptide bonds (3.4)
- C12N9/50—Proteinases, e.g. Endopeptidases (3.4.21-3.4.25)
- C12N9/58—Proteinases, e.g. Endopeptidases (3.4.21-3.4.25) derived from fungi
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
- C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
- C12N9/14—Hydrolases (3)
- C12N9/78—Hydrolases (3) acting on carbon to nitrogen bonds other than peptide bonds (3.5)
- C12N9/80—Hydrolases (3) acting on carbon to nitrogen bonds other than peptide bonds (3.5) acting on amide bonds in linear amides (3.5.1)
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Genetics & Genomics (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- General Engineering & Computer Science (AREA)
- Biomedical Technology (AREA)
- Biotechnology (AREA)
- Microbiology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Crystallography & Structural Chemistry (AREA)
- Biophysics (AREA)
- Mycology (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Enzymes And Modification Thereof (AREA)
- Peptides Or Proteins (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2395374A JPS5339513B2 (enrdf_load_stackoverflow) | 1974-02-28 | 1974-02-28 | |
| JP2884974A JPS5533880B2 (enrdf_load_stackoverflow) | 1974-03-12 | 1974-03-12 | |
| JP49040696A JPS5233094B2 (enrdf_load_stackoverflow) | 1974-04-10 | 1974-04-10 | |
| JP14520874A JPS537516B2 (enrdf_load_stackoverflow) | 1974-12-17 | 1974-12-17 | |
| JP14647474A JPS5173187A (en) | 1974-12-19 | 1974-12-19 | nn ashirupeputaidoruibunkaikosono seizoho |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1040123A true CA1040123A (en) | 1978-10-10 |
Family
ID=27520592
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA221,066A Expired CA1040123A (en) | 1974-02-28 | 1975-02-27 | Physiologically active peptide and its n-acyl derivatives and processes for producing thereof |
Country Status (4)
| Country | Link |
|---|---|
| CA (1) | CA1040123A (enrdf_load_stackoverflow) |
| DE (1) | DE2506601C3 (enrdf_load_stackoverflow) |
| FR (1) | FR2262532B1 (enrdf_load_stackoverflow) |
| GB (1) | GB1493969A (enrdf_load_stackoverflow) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5424845A (en) * | 1977-07-22 | 1979-02-24 | Microbial Chem Res Found | Novel bio-active peptide and its derivative |
| US4384994A (en) * | 1981-10-08 | 1983-05-24 | Merck & Co., Inc. | Renin inhibitory peptides |
| CA1258748A (en) * | 1981-10-08 | 1989-08-22 | Daniel F. Veber | Renin inhibitory peptides |
| CA1245217A (en) * | 1981-12-10 | 1988-11-22 | Joshua S. Boger | Renin inhibitory peptides having phe su13 xx deletion |
| FR2531951A1 (fr) * | 1982-08-17 | 1984-02-24 | Sanofi Sa | Derives peptidiques inhibiteurs de proteases acides, procede pour leur preparation et medicaments qui en contiennent |
-
1975
- 1975-02-17 DE DE19752506601 patent/DE2506601C3/de not_active Expired
- 1975-02-18 GB GB681975A patent/GB1493969A/en not_active Expired
- 1975-02-25 FR FR7505849A patent/FR2262532B1/fr not_active Expired
- 1975-02-27 CA CA221,066A patent/CA1040123A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE2506601B2 (de) | 1980-04-24 |
| FR2262532B1 (enrdf_load_stackoverflow) | 1978-12-22 |
| FR2262532A1 (enrdf_load_stackoverflow) | 1975-09-26 |
| DE2506601A1 (de) | 1975-09-04 |
| GB1493969A (en) | 1977-12-07 |
| DE2506601C3 (de) | 1980-12-11 |
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