CA1129847A - Substrates for angiotensin converting enzyme - Google Patents
Substrates for angiotensin converting enzymeInfo
- Publication number
- CA1129847A CA1129847A CA302,876A CA302876A CA1129847A CA 1129847 A CA1129847 A CA 1129847A CA 302876 A CA302876 A CA 302876A CA 1129847 A CA1129847 A CA 1129847A
- Authority
- CA
- Canada
- Prior art keywords
- compound
- substrate
- enzyme
- iodo
- remnant
- 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
- 239000000758 substrate Substances 0.000 title claims abstract description 95
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- 102000004270 Peptidyl-Dipeptidase A Human genes 0.000 title claims description 45
- 108090000882 Peptidyl-Dipeptidase A Proteins 0.000 title claims description 45
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- 108090000765 processed proteins & peptides Proteins 0.000 claims abstract description 15
- 239000003960 organic solvent Substances 0.000 claims abstract description 10
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 5
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical group CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 51
- 238000000034 method Methods 0.000 claims description 34
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- YFFIDNWSAVHIRP-FKBYEOEOSA-N (2s)-2-[[(2s)-2-[[(2s)-1-benzoylpyrrolidine-2-carbonyl]amino]-3-phenylpropanoyl]amino]-5-(diaminomethylideneamino)pentanoic acid Chemical group C([C@@H](C(=O)N[C@@H](CCCNC(=N)N)C(O)=O)NC(=O)[C@H]1N(CCC1)C(=O)C=1C=CC=CC=1)C1=CC=CC=C1 YFFIDNWSAVHIRP-FKBYEOEOSA-N 0.000 claims 5
- CYQZRSVDAIOAIY-UHFFFAOYSA-N 2-[[2-[(2-benzamidoacetyl)amino]acetyl]amino]acetic acid Chemical group OC(=O)CNC(=O)CNC(=O)CNC(=O)C1=CC=CC=C1 CYQZRSVDAIOAIY-UHFFFAOYSA-N 0.000 claims 4
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- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 2
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- XMBWDFGMSWQBCA-YPZZEJLDSA-N iodane Chemical group [125IH] XMBWDFGMSWQBCA-YPZZEJLDSA-N 0.000 claims 2
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- 239000011541 reaction mixture Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 6
- QIAFMBKCNZACKA-UHFFFAOYSA-N N-benzoylglycine Chemical compound OC(=O)CNC(=O)C1=CC=CC=C1 QIAFMBKCNZACKA-UHFFFAOYSA-N 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
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- 102400000345 Angiotensin-2 Human genes 0.000 description 4
- 101800000733 Angiotensin-2 Proteins 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
- CZGUSIXMZVURDU-JZXHSEFVSA-N Ile(5)-angiotensin II Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC=1C=CC=CC=1)C([O-])=O)NC(=O)[C@@H](NC(=O)[C@H](CCCNC(N)=[NH2+])NC(=O)[C@@H]([NH3+])CC([O-])=O)C(C)C)C1=CC=C(O)C=C1 CZGUSIXMZVURDU-JZXHSEFVSA-N 0.000 description 4
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
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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
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/08—Tripeptides
- C07K5/0821—Tripeptides with the first amino acid being heterocyclic, e.g. His, Pro, Trp
- C07K5/0823—Tripeptides with the first amino acid being heterocyclic, e.g. His, Pro, Trp and Pro-amino acid; Derivatives thereof
-
- 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
- C07K5/0802—Tripeptides with the first amino acid being neutral
- C07K5/0804—Tripeptides with the first amino acid being neutral and aliphatic
- C07K5/0806—Tripeptides with the first amino acid being neutral and aliphatic the side chain containing 0 or 1 carbon atoms, i.e. Gly, Ala
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12Q—MEASURING OR TESTING PROCESSES INVOLVING ENZYMES, NUCLEIC ACIDS OR MICROORGANISMS; COMPOSITIONS OR TEST PAPERS THEREFOR; PROCESSES OF PREPARING SUCH COMPOSITIONS; CONDITION-RESPONSIVE CONTROL IN MICROBIOLOGICAL OR ENZYMOLOGICAL PROCESSES
- C12Q1/00—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions
- C12Q1/34—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving hydrolase
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12Q—MEASURING OR TESTING PROCESSES INVOLVING ENZYMES, NUCLEIC ACIDS OR MICROORGANISMS; COMPOSITIONS OR TEST PAPERS THEREFOR; PROCESSES OF PREPARING SUCH COMPOSITIONS; CONDITION-RESPONSIVE CONTROL IN MICROBIOLOGICAL OR ENZYMOLOGICAL PROCESSES
- C12Q1/00—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions
- C12Q1/34—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving hydrolase
- C12Q1/37—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving hydrolase involving peptidase or proteinase
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N2333/00—Assays involving biological materials from specific organisms or of a specific nature
- G01N2333/90—Enzymes; Proenzymes
- G01N2333/914—Hydrolases (3)
- G01N2333/948—Hydrolases (3) acting on peptide bonds (3.4)
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N2333/00—Assays involving biological materials from specific organisms or of a specific nature
- G01N2333/90—Enzymes; Proenzymes
- G01N2333/914—Hydrolases (3)
- G01N2333/948—Hydrolases (3) acting on peptide bonds (3.4)
- G01N2333/95—Proteinases, i.e. endopeptidases (3.4.21-3.4.99)
- G01N2333/964—Proteinases, i.e. endopeptidases (3.4.21-3.4.99) derived from animal tissue
- G01N2333/96425—Proteinases, i.e. endopeptidases (3.4.21-3.4.99) derived from animal tissue from mammals
- G01N2333/96427—Proteinases, i.e. endopeptidases (3.4.21-3.4.99) derived from animal tissue from mammals in general
- G01N2333/9643—Proteinases, i.e. endopeptidases (3.4.21-3.4.99) derived from animal tissue from mammals in general with EC number
- G01N2333/96486—Metalloendopeptidases (3.4.24)
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Genetics & Genomics (AREA)
- Zoology (AREA)
- Engineering & Computer Science (AREA)
- Biophysics (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Microbiology (AREA)
- Physics & Mathematics (AREA)
- General Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Analytical Chemistry (AREA)
- Immunology (AREA)
- Biotechnology (AREA)
- Medicinal Chemistry (AREA)
- Investigating Or Analysing Biological Materials (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Peptides Or Proteins (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/795,497 US4115374A (en) | 1977-05-10 | 1977-05-10 | Substrates for angiotensin converting enzyme |
| US795,497 | 1977-05-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1129847A true CA1129847A (en) | 1982-08-17 |
Family
ID=25165666
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA302,876A Expired CA1129847A (en) | 1977-05-10 | 1978-05-08 | Substrates for angiotensin converting enzyme |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US4115374A (en, 2012) |
| CA (1) | CA1129847A (en, 2012) |
| DE (3) | DE2760342C2 (en, 2012) |
| GB (1) | GB1555832A (en, 2012) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4251628A (en) * | 1978-03-14 | 1981-02-17 | Ryan James W | Substrates for angiotensin converting enzyme |
| US4260682A (en) * | 1979-04-04 | 1981-04-07 | Ryan James W | High sensitivity assays for angiotensin converting enzyme |
| US4327178A (en) * | 1979-05-01 | 1982-04-27 | University Of Miami | Urinary kallikrein assay: specific substrates and assay method |
| US4372941A (en) * | 1980-09-05 | 1983-02-08 | Ryan James W | Novel radioassay procedure |
| JPS5935597B2 (ja) * | 1980-12-23 | 1984-08-29 | 富士レビオ株式会社 | アンジオテンシン変換酵素の活性測定法 |
| US4563305A (en) * | 1981-01-07 | 1986-01-07 | University Of Miami | Radiolabelled substrates for assaying mammalian enzymes |
| US4448715A (en) * | 1981-11-02 | 1984-05-15 | University Of Miami | Tagged pyroglu-L-Phe-L-Arg derivatives, substrates and assays for kallikrein |
| US5045303A (en) * | 1985-05-17 | 1991-09-03 | Neorx Corporation | Radiohalogenated small molecules for protein labeling |
| JPS62277331A (ja) * | 1986-04-21 | 1987-12-02 | ネオルツクス コ−ポレイシヨン | 蛋白質標識のための放射性ハロゲン化小分子 |
| US4883862A (en) * | 1988-04-13 | 1989-11-28 | Albert Einstein College Of Medicine - Of Yeshiva University | Mercaptosuccinyl glycyl-glycyl-glycine a complex thereof with Tc-99m, and methods of making the same |
| CN2409803Y (zh) * | 1999-12-21 | 2000-12-13 | 黄义全 | 导流通风安全帽 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4057629A (en) * | 1974-12-18 | 1977-11-08 | Daiichi Seiyaku Co., Ltd. | Tyrosine derivatives and process for preparing the same |
-
1977
- 1977-05-10 US US05/795,497 patent/US4115374A/en not_active Expired - Lifetime
- 1977-10-26 DE DE2760342A patent/DE2760342C2/de not_active Expired - Fee Related
- 1977-10-26 DE DE2760343A patent/DE2760343C2/de not_active Expired - Fee Related
- 1977-10-26 DE DE2747853A patent/DE2747853C2/de not_active Expired
- 1977-11-07 GB GB46226/77A patent/GB1555832A/en not_active Expired
-
1978
- 1978-05-08 CA CA302,876A patent/CA1129847A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE2760342A1 (en, 2012) | 1986-03-20 |
| DE2760343C2 (en, 2012) | 1990-06-28 |
| GB1555832A (en) | 1979-11-14 |
| DE2747853A1 (de) | 1978-11-23 |
| DE2760343A1 (en, 2012) | 1986-03-20 |
| DE2760342C2 (en, 2012) | 1990-06-28 |
| US4115374A (en) | 1978-09-19 |
| DE2747853C2 (de) | 1986-11-13 |
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Legal Events
| Date | Code | Title | Description |
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| MKEX | Expiry |