JPS6326871B2 - - Google Patents

Info

Publication number: JPS6326871B2
Authority: JP; Japan
Prior art keywords: gly; boc; leu; deaa; val
Prior art date: 1979-09-14
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

Application number

JP11733579A

Other languages

English (en)

Japanese (ja)

Other versions

JPS5642597A (en

Inventor

Yoshimasa Fujita

Chizuko Nakahara

Shigenori Tanaka

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Seikagaku Corp

Original Assignee

Seikagaku Corp

Priority date (The priority date 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 date listed.)

1979-09-14

Filing date

1979-09-14

Publication date

1988-05-31

1979-09-14 Application filed by Seikagaku Corp filed Critical Seikagaku Corp

1979-09-14 Priority to JP11733579A priority Critical patent/JPS5642597A/ja

1981-04-20 Publication of JPS5642597A publication Critical patent/JPS5642597A/ja

1988-05-31 Publication of JPS6326871B2 publication Critical patent/JPS6326871B2/ja

Status Granted legal-status Critical Current

Links

239000002158 endotoxin Substances 0.000 claims description 28
239000000758 substrate Substances 0.000 claims description 22
239000006166 lysate Substances 0.000 claims description 16
238000000034 method Methods 0.000 claims description 11
102000010911 Enzyme Precursors Human genes 0.000 claims description 8
108010062466 Enzyme Precursors Proteins 0.000 claims description 8
QNGVNLMMEQUVQK-UHFFFAOYSA-N 4-n,4-n-diethylbenzene-1,4-diamine Chemical compound CCN(CC)C1=CC=C(N)C=C1 QNGVNLMMEQUVQK-UHFFFAOYSA-N 0.000 claims description 6
241001529572 Chaceon affinis Species 0.000 claims description 6
238000002798 spectrophotometry method Methods 0.000 claims description 5
150000008575 L-amino acids Chemical group 0.000 claims description 4
PWJNDVAKQLOWRZ-UHFFFAOYSA-N 1-hydroxynaphthalene-2-sulfonic acid Chemical compound C1=CC=C2C(O)=C(S(O)(=O)=O)C=CC2=C1 PWJNDVAKQLOWRZ-UHFFFAOYSA-N 0.000 claims description 2
238000005691 oxidative coupling reaction Methods 0.000 claims description 2
108090000765 processed proteins & peptides Proteins 0.000 claims description 2
125000006239 protecting group Chemical group 0.000 claims description 2
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 17
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 14
150000001875 compounds Chemical class 0.000 description 14
FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 11
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
210000001124 body fluid Anatomy 0.000 description 10
239000010839 body fluid Substances 0.000 description 10
238000002360 preparation method Methods 0.000 description 10
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 7
FHOAKXBXYSJBGX-YFKPBYRVSA-N (2s)-3-hydroxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid Chemical compound CC(C)(C)OC(=O)N[C@@H](CO)C(O)=O FHOAKXBXYSJBGX-YFKPBYRVSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
238000002835 absorbance Methods 0.000 description 6
238000000921 elemental analysis Methods 0.000 description 6
102000004190 Enzymes Human genes 0.000 description 5
108090000790 Enzymes Proteins 0.000 description 5
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
241000239224 Tachypleus tridentatus Species 0.000 description 4
238000005904 alkaline hydrolysis reaction Methods 0.000 description 4
238000011088 calibration curve Methods 0.000 description 4
235000019646 color tone Nutrition 0.000 description 4
238000001514 detection method Methods 0.000 description 4
201000010099 disease Diseases 0.000 description 4
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
NTNZTEQNFHNYBC-UHFFFAOYSA-N ethyl 2-aminoacetate Chemical compound CCOC(=O)CN NTNZTEQNFHNYBC-UHFFFAOYSA-N 0.000 description 4
239000000243 solution Substances 0.000 description 4
239000000126 substance Substances 0.000 description 4
NRXDUMDULDHIEA-VIFPVBQESA-N 2-[[(2s)-4-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoyl]amino]acetic acid Chemical compound CC(C)(C)OC(=O)N[C@@H](CC(C)C)C(=O)NCC(O)=O NRXDUMDULDHIEA-VIFPVBQESA-N 0.000 description 3
BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 3
238000010521 absorption reaction Methods 0.000 description 3
238000003759 clinical diagnosis Methods 0.000 description 3
230000000052 comparative effect Effects 0.000 description 3
238000009833 condensation Methods 0.000 description 3
230000005494 condensation Effects 0.000 description 3
210000000087 hemolymph Anatomy 0.000 description 3
230000031700 light absorption Effects 0.000 description 3
239000002243 precursor Substances 0.000 description 3
239000002904 solvent Substances 0.000 description 3
208000024891 symptom Diseases 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
MIYQNOPLWKCHED-JTQLQIEISA-N (2s)-2-benzamido-3-methylbutanoic acid Chemical compound CC(C)[C@@H](C(O)=O)NC(=O)C1=CC=CC=C1 MIYQNOPLWKCHED-JTQLQIEISA-N 0.000 description 2
108700023418 Amidases Proteins 0.000 description 2
-1 Boc- Chemical class 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
208000037487 Endotoxemia Diseases 0.000 description 2
206010018910 Haemolysis Diseases 0.000 description 2
241000239218 Limulus Species 0.000 description 2
241000239220 Limulus polyphemus Species 0.000 description 2
102000005922 amidase Human genes 0.000 description 2
238000003556 assay Methods 0.000 description 2
210000004369 blood Anatomy 0.000 description 2
239000008280 blood Substances 0.000 description 2
239000000872 buffer Substances 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
238000000354 decomposition reaction Methods 0.000 description 2
230000018044 dehydration Effects 0.000 description 2
238000006297 dehydration reaction Methods 0.000 description 2
238000010586 diagram Methods 0.000 description 2
239000000975 dye Substances 0.000 description 2
230000000694 effects Effects 0.000 description 2
238000010931 ester hydrolysis Methods 0.000 description 2
PMKXAKKWRBOEIC-QMMMGPOBSA-N ethyl 2-[[(2s)-2-amino-4-methylpentanoyl]amino]acetate Chemical compound CCOC(=O)CNC(=O)[C@@H](N)CC(C)C PMKXAKKWRBOEIC-QMMMGPOBSA-N 0.000 description 2
239000012530 fluid Substances 0.000 description 2
230000008588 hemolysis Effects 0.000 description 2
230000002401 inhibitory effect Effects 0.000 description 2
238000005259 measurement Methods 0.000 description 2
229910052763 palladium Inorganic materials 0.000 description 2
230000002829 reductive effect Effects 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
238000012360 testing method Methods 0.000 description 2
POLGZPYHEPOBFG-NSHDSACASA-N (2s)-2-benzamido-4-methylpentanoic acid Chemical compound CC(C)C[C@@H](C(O)=O)NC(=O)C1=CC=CC=C1 POLGZPYHEPOBFG-NSHDSACASA-N 0.000 description 1
SZXBQTSZISFIAO-ZETCQYMHSA-N (2s)-3-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanoic acid Chemical compound CC(C)[C@@H](C(O)=O)NC(=O)OC(C)(C)C SZXBQTSZISFIAO-ZETCQYMHSA-N 0.000 description 1
PUUABEGDHGDROR-RYUDHWBXSA-N (2s)-4-methyl-2-[[(2s)-3-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanoyl]amino]pentanoic acid Chemical compound CC(C)C[C@@H](C(O)=O)NC(=O)[C@H](C(C)C)NC(=O)OC(C)(C)C PUUABEGDHGDROR-RYUDHWBXSA-N 0.000 description 1
OZSSOVRIEPAIMP-ZETCQYMHSA-N (2s)-5-[amino(nitramido)methylidene]azaniumyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoate Chemical compound CC(C)(C)OC(=O)N[C@H](C(O)=O)CCCN=C(N)N[N+]([O-])=O OZSSOVRIEPAIMP-ZETCQYMHSA-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
206010003445 Ascites Diseases 0.000 description 1
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
206010023126 Jaundice Diseases 0.000 description 1
108010093008 Kinins Proteins 0.000 description 1
102000002397 Kinins Human genes 0.000 description 1
206010067125 Liver injury Diseases 0.000 description 1
241000872931 Myoporum sandwicense Species 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
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
229920005654 Sephadex Polymers 0.000 description 1
239000012507 Sephadex™ Substances 0.000 description 1
206010040070 Septic Shock Diseases 0.000 description 1
241000239222 Tachypleus Species 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
230000003213 activating effect Effects 0.000 description 1
238000001042 affinity chromatography Methods 0.000 description 1
239000003513 alkali Substances 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
210000000941 bile Anatomy 0.000 description 1
210000000601 blood cell Anatomy 0.000 description 1
230000023555 blood coagulation Effects 0.000 description 1
210000004556 brain Anatomy 0.000 description 1
239000007853 buffer solution Substances 0.000 description 1
108010071063 butyloxycarbonyl-leucyl-glycyl-arginine-4-nitroanilide Proteins 0.000 description 1
239000001110 calcium chloride Substances 0.000 description 1
235000011148 calcium chloride Nutrition 0.000 description 1
229910001628 calcium chloride Inorganic materials 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
239000003086 colorant Substances 0.000 description 1
238000004040 coloring Methods 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
239000007859 condensation product Substances 0.000 description 1
238000011109 contamination Methods 0.000 description 1
238000005520 cutting process Methods 0.000 description 1
230000007423 decrease Effects 0.000 description 1
238000007865 diluting Methods 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
239000003814 drug Substances 0.000 description 1
238000001962 electrophoresis Methods 0.000 description 1
108010072542 endotoxin binding proteins Proteins 0.000 description 1
230000002255 enzymatic effect Effects 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
239000003527 fibrinolytic agent Substances 0.000 description 1
230000003480 fibrinolytic effect Effects 0.000 description 1
238000002523 gelfiltration Methods 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
231100000234 hepatic damage Toxicity 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 1
239000000815 hypotonic solution Substances 0.000 description 1
230000008105 immune reaction Effects 0.000 description 1
208000015181 infectious disease Diseases 0.000 description 1
230000002452 interceptive effect Effects 0.000 description 1
230000000968 intestinal effect Effects 0.000 description 1
238000001155 isoelectric focusing Methods 0.000 description 1
238000012454 limulus amebocyte lysate test Methods 0.000 description 1
210000004185 liver Anatomy 0.000 description 1
230000008818 liver damage Effects 0.000 description 1
210000004880 lymph fluid Anatomy 0.000 description 1
210000000865 mononuclear phagocyte system Anatomy 0.000 description 1
210000000056 organ Anatomy 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
210000001819 pancreatic juice Anatomy 0.000 description 1
230000007170 pathology Effects 0.000 description 1
230000007310 pathophysiology Effects 0.000 description 1
239000008188 pellet Substances 0.000 description 1
230000000737 periodic effect Effects 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
239000002504 physiological saline solution Substances 0.000 description 1
239000000049 pigment Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
238000012802 pre-warming Methods 0.000 description 1
238000012545 processing Methods 0.000 description 1
239000000047 product Substances 0.000 description 1
238000011002 quantification Methods 0.000 description 1
238000006894 reductive elimination reaction Methods 0.000 description 1
238000011160 research Methods 0.000 description 1
230000004044 response Effects 0.000 description 1
238000007127 saponification reaction Methods 0.000 description 1
230000007017 scission Effects 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
RQSBRFZHUKLKNO-VIFPVBQESA-N tert-butyl n-[(2s)-4-methyl-1-oxopentan-2-yl]carbamate Chemical compound CC(C)C[C@@H](C=O)NC(=O)OC(C)(C)C RQSBRFZHUKLKNO-VIFPVBQESA-N 0.000 description 1
239000012085 test solution Substances 0.000 description 1
239000003053 toxin Substances 0.000 description 1
231100000765 toxin Toxicity 0.000 description 1
210000002700 urine Anatomy 0.000 description 1
238000005303 weighing Methods 0.000 description 1

Landscapes

Investigating Or Analysing Biological Materials (AREA)
Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)

JP11733579A 1979-09-14 1979-09-14 Determination of intracellular toxicin using new synthetic substrate Granted JPS5642597A (en)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP11733579A JPS5642597A (en)	1979-09-14	1979-09-14	Determination of intracellular toxicin using new synthetic substrate

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP11733579A JPS5642597A (en)	1979-09-14	1979-09-14	Determination of intracellular toxicin using new synthetic substrate

Related Child Applications (1)

Application Number	Title	Priority Date	Filing Date
JP1057818A Division JPH02192A (ja)	1989-03-13	1989-03-13	新規合成基質

Publications (2)

Publication Number	Publication Date
JPS5642597A JPS5642597A (en)	1981-04-20
JPS6326871B2 true JPS6326871B2 (fr)	1988-05-31

Family

ID=14709167

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP11733579A Granted JPS5642597A (en)	1979-09-14	1979-09-14	Determination of intracellular toxicin using new synthetic substrate

Country Status (1)

Country	Link
JP (1)	JPS5642597A (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO2017141961A1 (fr)	2016-02-16	2017-08-24	生化学工業株式会社	Mesure électrochimique utilisant un dérivé de phénylènediamine

1979
- 1979-09-14 JP JP11733579A patent/JPS5642597A/ja active Granted

Also Published As

Publication number	Publication date
JPS5642597A (en)	1981-04-20

Publication	Publication Date	Title
JP3524120B2 (ja)	2004-05-10	前処理剤、前処理方法、前処理された試料による測定法、測定用キット及び試料の判定方法
CA1201048A (fr)	1986-02-25	Methode d'analyse des endotoxines bacteriennes et trousse utilisee a cet effet
Fuller et al.	1971	Invertebrate fibrinogen. I. Purification and characterization of fibrinogen from the spiny lobster
US4188264A (en)	1980-02-12	Process for determining bacterial endotoxin and reagents used therefor
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PL172042B1 (pl)	1997-07-31	Zestaw testowy do wykrywania Helicobacter pyroli PL PL PL
Braymer et al.	1971	Chemical and physical studies of Neurospora crassa invertase. Molecular weight, amino acid and carbohydrate composition, and quaternary structure
JP3402476B2 (ja)	2003-05-06	リポ多糖結合性タンパク質及びその製造法
EP0096689A1 (fr)	1983-12-28	Procede et agent de reaction pour detecter des endotoxines ou des beta-1,3 glucanes a partir de champignons ou bacteries
Tu et al.	1971	Isolation and characterization of the toxic component of Enhydrina schistosa (common sea snake) venom
EP0041089B1 (fr)	1986-04-23	Procédé chromogène pour la détection d'une endotoxine dans le sang
EP0549102B1 (fr)	1996-07-03	Réactifs et procédés pour déterminer des Beta-Glucanes
KR100217964B1 (ko)	1999-10-01	프로페놀옥시다제 활성화 효소의 활성 측정법 및 이의 용도
JPS6326871B2 (fr)	1988-05-31
JPH0311760B2 (fr)	1991-02-18
JPH02500856A (ja)	1990-03-22	エンドトキシンアッセイ
JPH07155196A (ja)	1995-06-20	生体成分の測定法
JPH083486B2 (ja)	1996-01-17	体液中の基底膜コラーゲンの測定法及び基底膜コラーゲン―ドメインｎｃ１に対する抗体の検出法
JP3044569B2 (ja)	2000-05-22	ヒトｃ―ペプチドの測定方法
Manjula et al.	1976	DEAMIDATED ACTIVE INTERMEDIATES IN THE IRREVERSIBLE ACID DENATURATION OF RIBONUCLEASE‐A
Jones et al.	1983	Studies on the structure of sphingomyelinase. Amino acid composition and heterogeneity on isoelectric focusing
JP3614849B2 (ja)	2005-01-26	前処理剤、前処理方法、前処理された試料による測定法、測定用キット及び試料の判定方法
JP3658782B2 (ja)	2005-06-08	プロフェノールオキシダーゼ活性化酵素の活性測定法およびその応用
JPS6154400B2 (fr)	1986-11-21
JP2688773B2 (ja)	1997-12-10	エンドトキシンの不活化方法