SU588927A3 - Способ получени пепстатинов - Google Patents
Способ получени пепстатиновInfo
- Publication number
- SU588927A3 SU588927A3 SU721762234A SU1762234A SU588927A3 SU 588927 A3 SU588927 A3 SU 588927A3 SU 721762234 A SU721762234 A SU 721762234A SU 1762234 A SU1762234 A SU 1762234A SU 588927 A3 SU588927 A3 SU 588927A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- pepstatin
- methanol
- powder
- new
- precipitate
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 86
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 36
- 108010091212 pepstatin Proteins 0.000 claims description 26
- 229950000964 pepstatin Drugs 0.000 claims description 26
- 239000000843 powder Substances 0.000 claims description 26
- FAXGPCHRFPCXOO-LXTPJMTPSA-N pepstatin A Chemical compound OC(=O)C[C@H](O)[C@H](CC(C)C)NC(=O)[C@H](C)NC(=O)C[C@H](O)[C@H](CC(C)C)NC(=O)[C@H](C(C)C)NC(=O)[C@H](C(C)C)NC(=O)CC(C)C FAXGPCHRFPCXOO-LXTPJMTPSA-N 0.000 claims description 24
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 16
- 239000002244 precipitate Substances 0.000 claims description 15
- 238000000354 decomposition reaction Methods 0.000 claims description 13
- 239000000126 substance Substances 0.000 claims description 12
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 11
- 239000013078 crystal Substances 0.000 claims description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 10
- 238000003756 stirring Methods 0.000 claims description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 8
- 108010036222 Pepstatins Proteins 0.000 claims description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 7
- QTNFTTFYVXJGEA-XAFAIMEYSA-N CCCCCC(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC(C)C)[C@@H](O)CC(=O)N[C@@H](C)C(=O)N[C@@H](CC(C)C)[C@@H](O)CC(O)=O Chemical compound CCCCCC(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC(C)C)[C@@H](O)CC(=O)N[C@@H](C)C(=O)N[C@@H](CC(C)C)[C@@H](O)CC(O)=O QTNFTTFYVXJGEA-XAFAIMEYSA-N 0.000 claims description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 6
- 230000002467 anti-pepsin effect Effects 0.000 claims description 6
- 239000008267 milk Substances 0.000 claims description 6
- 239000000243 solution Substances 0.000 claims description 6
- 239000006188 syrup Substances 0.000 claims description 6
- 235000020357 syrup Nutrition 0.000 claims description 6
- 239000002021 butanolic extract Substances 0.000 claims description 5
- 150000004702 methyl esters Chemical class 0.000 claims description 5
- 235000013336 milk Nutrition 0.000 claims description 5
- 210000004080 milk Anatomy 0.000 claims description 5
- -1 pepstatin methyl ester Chemical class 0.000 claims description 5
- 102000057297 Pepsin A Human genes 0.000 claims description 4
- 108090000284 Pepsin A Proteins 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 4
- 229940111202 pepsin Drugs 0.000 claims description 4
- 239000011541 reaction mixture Substances 0.000 claims description 4
- 239000012141 concentrate Substances 0.000 claims description 3
- 235000008504 concentrate Nutrition 0.000 claims description 3
- 239000012531 culture fluid Substances 0.000 claims description 3
- 230000000694 effects Effects 0.000 claims description 3
- 238000004809 thin layer chromatography Methods 0.000 claims description 3
- 238000001914 filtration Methods 0.000 claims description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical class N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims 4
- 239000002253 acid Substances 0.000 claims 3
- 238000004587 chromatography analysis Methods 0.000 claims 3
- 238000002425 crystallisation Methods 0.000 claims 3
- 230000008025 crystallization Effects 0.000 claims 3
- 239000000706 filtrate Substances 0.000 claims 3
- 239000000693 micelle Substances 0.000 claims 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims 2
- 235000010469 Glycine max Nutrition 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 239000005018 casein Substances 0.000 claims 2
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 claims 2
- 235000021240 caseins Nutrition 0.000 claims 2
- 125000004494 ethyl ester group Chemical group 0.000 claims 2
- 235000013312 flour Nutrition 0.000 claims 2
- 235000011187 glycerol Nutrition 0.000 claims 2
- 238000010438 heat treatment Methods 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 239000000047 product Substances 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 239000002002 slurry Substances 0.000 claims 2
- JOKUGRFMJJOCQE-XAFAIMEYSA-N CC(C)CCC(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC(C)C)[C@@H](O)CC(=O)N[C@@H](C)C(=O)N[C@@H](CC(C)C)[C@@H](O)CC(O)=O Chemical compound CC(C)CCC(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC(C)C)[C@@H](O)CC(=O)N[C@@H](C)C(=O)N[C@@H](CC(C)C)[C@@H](O)CC(O)=O JOKUGRFMJJOCQE-XAFAIMEYSA-N 0.000 claims 1
- 244000068988 Glycine max Species 0.000 claims 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 claims 1
- 240000006240 Linum usitatissimum Species 0.000 claims 1
- 235000004431 Linum usitatissimum Nutrition 0.000 claims 1
- QOSMNYMQXIVWKY-UHFFFAOYSA-N Propyl levulinate Chemical compound CCCOC(=O)CCC(C)=O QOSMNYMQXIVWKY-UHFFFAOYSA-N 0.000 claims 1
- 125000005907 alkyl ester group Chemical group 0.000 claims 1
- 239000007864 aqueous solution Substances 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 238000009835 boiling Methods 0.000 claims 1
- KTUQUZJOVNIKNZ-UHFFFAOYSA-N butan-1-ol;hydrate Chemical compound O.CCCCO KTUQUZJOVNIKNZ-UHFFFAOYSA-N 0.000 claims 1
- 238000005119 centrifugation Methods 0.000 claims 1
- 230000032050 esterification Effects 0.000 claims 1
- 238000005886 esterification reaction Methods 0.000 claims 1
- 238000011534 incubation Methods 0.000 claims 1
- 229910052500 inorganic mineral Chemical class 0.000 claims 1
- 239000011707 mineral Chemical class 0.000 claims 1
- 235000015097 nutrients Nutrition 0.000 claims 1
- 238000001556 precipitation Methods 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 238000010992 reflux Methods 0.000 claims 1
- 239000013049 sediment Substances 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 239000007787 solid Substances 0.000 claims 1
- 239000000725 suspension Substances 0.000 claims 1
- 239000000052 vinegar Substances 0.000 claims 1
- 235000021419 vinegar Nutrition 0.000 claims 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 239000011550 stock solution Substances 0.000 description 2
- IYAHYZQOYHDKNN-UHFFFAOYSA-N COC(=O)c1c(C)c(Cc2c(O)c(C(O)=O)c(C)c3Oc4c(OC(=O)c23)c(C)cc(O)c4C=O)c(O)c(C)c1O Chemical compound COC(=O)c1c(C)c(Cc2c(O)c(C(O)=O)c(C)c3Oc4c(OC(=O)c23)c(C)cc(O)c4C=O)c(O)c(C)c1O IYAHYZQOYHDKNN-UHFFFAOYSA-N 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- BIECHDFOWIXSMP-UHFFFAOYSA-N Furfuric acid Natural products CC1=C(O)C(C(=O)OC)=C(C)C(CC=2C=3OC(=O)C4=C(C)C=C(O)C(C=O)=C4OC=3C(C)=C(C(O)=O)C=2O)=C1O BIECHDFOWIXSMP-UHFFFAOYSA-N 0.000 description 1
- 238000005273 aeration Methods 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 159000000011 group IA salts Chemical class 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 238000000954 titration curve Methods 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
- C07K7/02—Linear peptides containing at least one abnormal peptide link
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Biochemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Biophysics (AREA)
- Oncology (AREA)
- Crystallography & Structural Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Communicable Diseases (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Electrolytic Production Of Non-Metals, Compounds, Apparatuses Therefor (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1729271A JPS547876B1 (enrdf_load_stackoverflow) | 1971-03-26 | 1971-03-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU588927A3 true SU588927A3 (ru) | 1978-01-15 |
Family
ID=11939901
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU721762234A SU588927A3 (ru) | 1971-03-26 | 1972-03-22 | Способ получени пепстатинов |
Country Status (27)
-
1971
- 1971-03-24 PH PH13386A patent/PH10703A/en unknown
- 1971-03-26 JP JP1729271A patent/JPS547876B1/ja active Pending
-
1972
- 1972-03-08 GB GB1088772A patent/GB1394231A/en not_active Expired
- 1972-03-10 IL IL38954A patent/IL38954A/xx unknown
- 1972-03-10 ZA ZA721668A patent/ZA721668B/xx unknown
- 1972-03-12 EG EG98/72A patent/EG10462A/xx active
- 1972-03-15 ES ES400777A patent/ES400777A1/es not_active Expired
- 1972-03-20 CH CH410972A patent/CH577557A5/xx not_active IP Right Cessation
- 1972-03-20 IE IE351/72A patent/IE36183B1/xx unknown
- 1972-03-21 RO RO7200070202A patent/RO62299A/ro unknown
- 1972-03-21 DE DE2213674A patent/DE2213674C3/de not_active Expired
- 1972-03-21 CS CS1889A patent/CS174828B2/cs unknown
- 1972-03-22 SU SU721762234A patent/SU588927A3/ru active
- 1972-03-24 NO NO1010/72A patent/NO136051C/no unknown
- 1972-03-24 DK DK144272A patent/DK131792C/da active
- 1972-03-24 LU LU65036D patent/LU65036A1/xx unknown
- 1972-03-24 HU HUZA343A patent/HU166530B/hu unknown
- 1972-03-24 CA CA138,010A patent/CA976899A/en not_active Expired
- 1972-03-24 FR FR7211143A patent/FR2130730B1/fr not_active Expired
- 1972-03-24 BE BE781253A patent/BE781253A/xx not_active IP Right Cessation
- 1972-03-24 YU YU795/72A patent/YU35274B/xx unknown
- 1972-03-25 PL PL1972154328A patent/PL88968B1/pl unknown
- 1972-03-27 SE SE7203975A patent/SE399909B/xx unknown
- 1972-03-27 FI FI720847A patent/FI48474C/fi active
- 1972-03-27 AT AT264572A patent/AT316463B/de not_active IP Right Cessation
- 1972-03-27 BG BG020069A patent/BG19809A3/xx unknown
- 1972-03-27 BG BG23999A patent/BG20616A3/xx unknown
- 1972-08-25 NL NL7204068.A patent/NL165501C/xx not_active IP Right Cessation
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