CS199631B2 - Method of producing new chromogen enzyme substrate - Google Patents
Method of producing new chromogen enzyme substrate Download PDFInfo
- Publication number
- CS199631B2 CS199631B2 CS764543A CS454376A CS199631B2 CS 199631 B2 CS199631 B2 CS 199631B2 CS 764543 A CS764543 A CS 764543A CS 454376 A CS454376 A CS 454376A CS 199631 B2 CS199631 B2 CS 199631B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- group
- lysine
- substrates
- reaction
- terminal
- Prior art date
Links
- 239000000758 substrate Substances 0.000 title claims description 49
- 102000004190 Enzymes Human genes 0.000 title claims description 24
- 108090000790 Enzymes Proteins 0.000 title claims description 24
- 238000000034 method Methods 0.000 title claims description 13
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims abstract description 13
- 239000004472 Lysine Substances 0.000 claims abstract description 10
- 150000001413 amino acids Chemical class 0.000 claims description 15
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical group NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims description 10
- 238000002523 gelfiltration Methods 0.000 claims description 9
- 125000006239 protecting group Chemical group 0.000 claims description 8
- 125000000637 arginyl group Chemical group N[C@@H](CCCNC(N)=N)C(=O)* 0.000 claims description 6
- AHLPHDHHMVZTML-BYPYZUCNSA-N ornithyl group Chemical group N[C@@H](CCCN)C(=O)O AHLPHDHHMVZTML-BYPYZUCNSA-N 0.000 claims description 6
- 210000004899 c-terminal region Anatomy 0.000 claims description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
- 108010022999 Serine Proteases Proteins 0.000 claims description 4
- 102000012479 Serine Proteases Human genes 0.000 claims description 4
- 108010016626 Dipeptides Proteins 0.000 claims description 3
- 239000012634 fragment Substances 0.000 claims description 3
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- 238000004519 manufacturing process Methods 0.000 claims description 3
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- 244000137850 Marrubium vulgare Species 0.000 claims description 2
- IADUEWIQBXOCDZ-UHFFFAOYSA-N azetidine-2-carboxylic acid Chemical compound OC(=O)C1CCN1 IADUEWIQBXOCDZ-UHFFFAOYSA-N 0.000 claims description 2
- 239000000543 intermediate Substances 0.000 claims description 2
- 238000004255 ion exchange chromatography Methods 0.000 claims description 2
- 125000006501 nitrophenyl group Chemical group 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 abstract description 17
- 239000004475 Arginine Substances 0.000 abstract description 2
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- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 abstract 1
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- 229940088598 enzyme Drugs 0.000 description 22
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- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 description 3
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 3
- 150000008575 L-amino acids Chemical class 0.000 description 3
- AGPKZVBTJJNPAG-WHFBIAKZSA-N L-isoleucine Chemical compound CC[C@H](C)[C@H](N)C(O)=O AGPKZVBTJJNPAG-WHFBIAKZSA-N 0.000 description 3
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- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 3
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 3
- 239000000872 buffer Substances 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 235000019439 ethyl acetate Nutrition 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
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- 108090000915 Aminopeptidases Proteins 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
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- 229920002307 Dextran Polymers 0.000 description 2
- 108010088842 Fibrinolysin Proteins 0.000 description 2
- 108060005987 Kallikrein Proteins 0.000 description 2
- 102000001399 Kallikrein Human genes 0.000 description 2
- AHLPHDHHMVZTML-UHFFFAOYSA-N Orn-delta-NH2 Natural products NCCCC(N)C(O)=O AHLPHDHHMVZTML-UHFFFAOYSA-N 0.000 description 2
- UTJLXEIPEHZYQJ-UHFFFAOYSA-N Ornithine Natural products OC(=O)C(C)CCCN UTJLXEIPEHZYQJ-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 108090000190 Thrombin Proteins 0.000 description 2
- 108090000631 Trypsin Proteins 0.000 description 2
- 102000004142 Trypsin Human genes 0.000 description 2
- KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Chemical compound CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 description 2
- 230000004913 activation Effects 0.000 description 2
- 150000003862 amino acid derivatives Chemical class 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 230000008033 biological extinction Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 238000010828 elution Methods 0.000 description 2
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 239000013067 intermediate product Substances 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 229960003104 ornithine Drugs 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- UQDJGEHQDNVPGU-UHFFFAOYSA-N serine phosphoethanolamine Chemical compound [NH3+]CCOP([O-])(=O)OCC([NH3+])C([O-])=O UQDJGEHQDNVPGU-UHFFFAOYSA-N 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- 229960004072 thrombin Drugs 0.000 description 2
- 239000012588 trypsin Substances 0.000 description 2
- GQAAGJRJCUHPEZ-GLKKMWKASA-N (2s)-6-amino-2-[[2-[[(2r)-2-amino-3-methylbutanoyl]amino]-3-methylpentanoyl]amino]-n-(4-nitrophenyl)hexanamide Chemical compound CC(C)[C@@H](N)C(=O)NC(C(C)CC)C(=O)N[C@@H](CCCCN)C(=O)NC1=CC=C([N+]([O-])=O)C=C1 GQAAGJRJCUHPEZ-GLKKMWKASA-N 0.000 description 1
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 1
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- JQFZHHSQMKZLRU-IUCAKERBSA-N Arg-Lys Chemical group NCCCC[C@@H](C(O)=O)NC(=O)[C@@H](N)CCCN=C(N)N JQFZHHSQMKZLRU-IUCAKERBSA-N 0.000 description 1
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- 239000007983 Tris buffer Substances 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 235000004279 alanine Nutrition 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 108010062796 arginyllysine Proteins 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 150000001540 azides Chemical class 0.000 description 1
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000003593 chromogenic compound Substances 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 238000001952 enzyme assay Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- AGPKZVBTJJNPAG-UHFFFAOYSA-N isoleucine Natural products CCC(C)C(N)C(O)=O AGPKZVBTJJNPAG-UHFFFAOYSA-N 0.000 description 1
- 229960000310 isoleucine Drugs 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000401 methanolic extract Substances 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- HOGDNTQCSIKEEV-UHFFFAOYSA-N n'-hydroxybutanediamide Chemical compound NC(=O)CCC(=O)NO HOGDNTQCSIKEEV-UHFFFAOYSA-N 0.000 description 1
- 239000006225 natural substrate Substances 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 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
- 150000003141 primary amines Chemical class 0.000 description 1
- 230000005588 protonation Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000010802 sludge Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 238000002798 spectrophotometry method Methods 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 229960001322 trypsin Drugs 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- 239000004474 valine Substances 0.000 description 1
Classifications
-
- 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
- C12Q1/56—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving blood clotting factors, e.g. involving thrombin, thromboplastin, fibrinogen
-
- 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
- C07K5/0808—Tripeptides with the first amino acid being neutral and aliphatic the side chain containing 2 to 4 carbon atoms, e.g. Val, Ile, Leu
-
- 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
-
- 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
- C12Q2337/00—N-linked chromogens for determinations of peptidases and proteinases
- C12Q2337/10—Anilides
- C12Q2337/12—Para-Nitroanilides p-NA
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Biophysics (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Microbiology (AREA)
- Immunology (AREA)
- Biotechnology (AREA)
- Analytical Chemistry (AREA)
- Physics & Mathematics (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- Neurosurgery (AREA)
- Hematology (AREA)
- Medicinal Chemistry (AREA)
- Peptides Or Proteins (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE7507974A SE407571B (sv) | 1975-07-11 | 1975-07-11 | Nya kromogena enzymsubstrat for serinproteaser |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS199631B2 true CS199631B2 (en) | 1980-07-31 |
Family
ID=20325115
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS764543A CS199631B2 (en) | 1975-07-11 | 1976-07-08 | Method of producing new chromogen enzyme substrate |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US4214049A (en]) |
| JP (1) | JPS5224581A (en]) |
| AT (1) | AT349648B (en]) |
| AU (1) | AU497546B2 (en]) |
| BE (1) | BE843969A (en]) |
| CA (1) | CA1081212A (en]) |
| CH (1) | CH622285A5 (en]) |
| CS (1) | CS199631B2 (en]) |
| DD (1) | DD127320A5 (en]) |
| DE (1) | DE2629067A1 (en]) |
| DK (1) | DK146937C (en]) |
| ES (1) | ES449738A1 (en]) |
| FI (1) | FI56524C (en]) |
| FR (1) | FR2317278A1 (en]) |
| GB (1) | GB1510925A (en]) |
| IL (1) | IL49830A (en]) |
| IT (1) | IT1062604B (en]) |
| NL (1) | NL187693C (en]) |
| NO (1) | NO142812C (en]) |
| PL (1) | PL103098B1 (en]) |
| SE (1) | SE407571B (en]) |
| SU (1) | SU700060A3 (en]) |
| ZA (1) | ZA763585B (en]) |
Families Citing this family (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH634662A5 (de) * | 1976-05-28 | 1983-02-15 | Pentapharm Ag | Verwendung von tripeptidderivaten zur quantitativen bestimmung von plasminogen-aktivatoren. |
| SE7801373L (sv) * | 1978-02-07 | 1979-08-08 | Kabi Ab | Lett spjelkbara substrat for kvantifiering av proteaser |
| EP0009010B1 (en) * | 1978-07-18 | 1983-03-02 | Kabi AB | Bradykinin inhibiting tripeptide derivatives, process for their preparation and pharmaceutical preparations containing them |
| US4275153A (en) * | 1978-08-03 | 1981-06-23 | American Hospital Supply Corporation | Analytical fluorogenic substrates for proteolytic enzymes |
| JPS5537120A (en) * | 1978-09-06 | 1980-03-15 | Kanji Tsuchiya | Method and device for preparation of food from oilseed |
| JPS5559149A (en) * | 1978-10-30 | 1980-05-02 | Torii Yakuhin Kk | Aminoacid derivative |
| JPS59499B2 (ja) * | 1978-11-02 | 1984-01-07 | 味の素株式会社 | ペプチド誘導体 |
| US4327178A (en) | 1979-05-01 | 1982-04-27 | University Of Miami | Urinary kallikrein assay: specific substrates and assay method |
| CA1161431A (en) * | 1979-05-11 | 1984-01-31 | Lars G. Svendsen | Tripeptide derivatives |
| DE2936543A1 (de) * | 1979-09-10 | 1981-04-09 | Behringwerke Ag, 3550 Marburg | Chromogene verbindungen |
| CA1161432A (en) * | 1980-02-12 | 1984-01-31 | Lars G. Svendsen | Tripeptide derivatives and their application in assaying enzymes |
| DE3108322A1 (de) | 1980-03-18 | 1981-12-24 | Immuno Aktiengesellschaft für chemisch-medizinische Produkte, 1220 Wien | Chromogenes enzymsubstrat |
| DK155051C (da) * | 1980-05-06 | 1989-07-03 | Pentapharm Ag | Tripeptidderivater samt fremgangsmaade til kvantitativ analyse for proteolytiske enzymer under anvendelse deraf |
| US4568636A (en) * | 1981-03-25 | 1986-02-04 | Pentapharm Ag | Tripeptide derivatives |
| JPS57177985U (en]) * | 1981-04-30 | 1982-11-11 | ||
| US4510241A (en) * | 1981-09-03 | 1985-04-09 | Mallinckrodt, Inc. | Peptide-type substrates useful in the quantitative determination of endotoxin |
| US4406832A (en) * | 1981-09-03 | 1983-09-27 | Mallinckrodt, Inc. | Peptide-type substrates useful in the quantitative determination of endotoxin |
| JPS5863399A (ja) * | 1981-10-14 | 1983-04-15 | Nitto Boseki Co Ltd | 新規なプラスミン測定用基質 |
| ATE17262T1 (de) * | 1981-11-02 | 1986-01-15 | Pentapharm Ag | Verfahren zur quantitativen bestimmung von blutgerinnungsfaktor xii in humanplasma. |
| US4448715A (en) * | 1981-11-02 | 1984-05-15 | University Of Miami | Tagged pyroglu-L-Phe-L-Arg derivatives, substrates and assays for kallikrein |
| NL8201987A (nl) * | 1982-05-13 | 1983-12-01 | Tno | Werkwijze voor het bepalen van de activiteit van plasminogeenactivator van het weefseltype, alsmede voor gebruik bij deze werkwijze geschikte combinatie van het "kit"-type. |
| DE3244030A1 (de) * | 1982-11-27 | 1984-05-30 | Behringwerke Ag, 3550 Marburg | Chromogene verbindungen, verfahren zu ihrer herstellung und ihre verwendung |
| DK201084A (da) * | 1983-04-28 | 1984-10-29 | Kimberly Clark Co | Fremgangsmaade til bestemmelse af cathepsin b i naervaerelse af andre proteolytiske enzymer, og forbindelser til anvendelse ved fremgangsmaaden |
| EP0182929A1 (de) * | 1984-11-26 | 1986-06-04 | American Hospital Supply Corporation | Koaktivator zur Aktivierung von Protein C |
| DE3536903A1 (de) * | 1985-10-16 | 1987-04-16 | Boehringer Mannheim Gmbh | Verfahren zur photometrischen bestimmung von protein c |
| JPS62126196A (ja) * | 1985-11-26 | 1987-06-08 | Nitto Boseki Co Ltd | 新規なα１−アンチトリプシン測定用化合物 |
| DE3710937A1 (de) * | 1987-04-01 | 1988-10-13 | Boehringer Mannheim Gmbh | Chromogene verbindungen, ihre herstellung und verwendung als enzymsubstrate |
| JPH01112157A (ja) * | 1987-07-10 | 1989-04-28 | Yamanouchi Pharmaceut Co Ltd | 組織プラスミノーゲンアクチベーター活性の測定法，測定具及び測定用キット |
| JPH0383093U (en]) * | 1989-12-09 | 1991-08-23 | ||
| GB9110298D0 (en) * | 1991-05-13 | 1991-07-03 | Fujisawa Pharmaceutical Co | New peptide compound and a process for the preparation thereof |
| ES2162025T3 (es) | 1995-01-10 | 2001-12-16 | Hendrik Coenraad Hemker | Procedimientos para la determinacion del potencial de trombina endogena (etp) y sustratos de la trombina para su uso en esos procedimientos. |
| TWI865601B (zh) * | 2019-09-05 | 2024-12-11 | 國立大學法人東京農工大學 | 類胰蛋白酶活性測定用基質 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE380257B (sv) * | 1972-05-02 | 1975-11-03 | Bofors Ab | Nya diagnostiskt verksamma substrat med hog specificitet till trombin och andra proteolytiska enzymer av typen peptidyl-peptid-hydrolaser |
| SE380258B (sv) * | 1972-05-02 | 1975-11-03 | Bofors Ab | Nya diagnostiskt verksamma substrat med hog specificitet till trypsin och andra enzymer av typen peptidyl-peptid-hydrolaser |
| DE2527932C2 (de) * | 1974-07-02 | 1983-04-21 | Pentapharm AG, 4052 Basel | Säureadditionssalze von Tripeptidderivaten und deren Verwendung als Substrate zur Bestimmung von Plasmakallikrein |
| SE407058B (sv) * | 1974-12-05 | 1979-03-12 | Kabi Ab | Nya kromogena enzymsubstrat for serinproteaser |
| CH622286A5 (en]) * | 1975-06-23 | 1981-03-31 | Pentapharm Ag |
-
1975
- 1975-07-11 SE SE7507974A patent/SE407571B/sv not_active IP Right Cessation
-
1976
- 1976-06-16 ZA ZA763585A patent/ZA763585B/xx unknown
- 1976-06-17 IL IL49830A patent/IL49830A/xx unknown
- 1976-06-18 GB GB25411/76A patent/GB1510925A/en not_active Expired
- 1976-06-25 AU AU15304/76A patent/AU497546B2/en not_active Expired
- 1976-06-25 AT AT464076A patent/AT349648B/de not_active IP Right Cessation
- 1976-06-29 DE DE19762629067 patent/DE2629067A1/de active Granted
- 1976-07-06 NL NLAANVRAGE7607433,A patent/NL187693C/xx not_active IP Right Cessation
- 1976-07-08 CS CS764543A patent/CS199631B2/cs unknown
- 1976-07-09 DK DK312776A patent/DK146937C/da not_active IP Right Cessation
- 1976-07-09 DD DD193794A patent/DD127320A5/xx unknown
- 1976-07-09 ES ES449738A patent/ES449738A1/es not_active Expired
- 1976-07-09 FI FI762009A patent/FI56524C/fi not_active IP Right Cessation
- 1976-07-09 PL PL1976191067A patent/PL103098B1/pl unknown
- 1976-07-09 IT IT50363/76A patent/IT1062604B/it active
- 1976-07-09 SU SU762379653A patent/SU700060A3/ru active
- 1976-07-09 NO NO762406A patent/NO142812C/no unknown
- 1976-07-09 BE BE168773A patent/BE843969A/xx not_active IP Right Cessation
- 1976-07-09 CA CA256,705A patent/CA1081212A/en not_active Expired
- 1976-07-09 CH CH887176A patent/CH622285A5/de not_active IP Right Cessation
- 1976-07-09 FR FR7621195A patent/FR2317278A1/fr active Granted
- 1976-07-10 JP JP51082441A patent/JPS5224581A/ja active Granted
-
1978
- 1978-10-27 US US05/955,441 patent/US4214049A/en not_active Expired - Lifetime
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