PL87546B1 - - Google Patents
Download PDFInfo
- Publication number
- PL87546B1 PL87546B1 PL1973164318A PL16431873A PL87546B1 PL 87546 B1 PL87546 B1 PL 87546B1 PL 1973164318 A PL1973164318 A PL 1973164318A PL 16431873 A PL16431873 A PL 16431873A PL 87546 B1 PL87546 B1 PL 87546B1
- Authority
- PL
- Poland
- Prior art keywords
- tetaine
- water
- mass
- crystallization
- acetone
- Prior art date
Links
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
- XFOUAXMJRHNTOP-PFQXTLEHSA-N bacilysin Chemical compound C[C@H]([NH3+])C(=O)N[C@H](C([O-])=O)C[C@@H]1CCC(=O)[C@@H]2O[C@H]12 XFOUAXMJRHNTOP-PFQXTLEHSA-N 0.000 claims description 13
- 108700023668 bacilysin Proteins 0.000 claims description 13
- 150000002500 ions Chemical class 0.000 claims description 11
- 238000002425 crystallisation Methods 0.000 claims description 10
- 230000008025 crystallization Effects 0.000 claims description 10
- 238000003795 desorption Methods 0.000 claims description 10
- 238000004458 analytical method Methods 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 5
- 238000001228 spectrum Methods 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 3
- 125000000524 functional group Chemical group 0.000 claims description 3
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 3
- 102000004196 processed proteins & peptides Human genes 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 150000007513 acids Chemical class 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- -1 amino- Chemical class 0.000 claims description 2
- 238000004809 thin layer chromatography Methods 0.000 claims 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- 238000004949 mass spectrometry Methods 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- 102000004190 Enzymes Human genes 0.000 description 4
- 108090000790 Enzymes Proteins 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- 230000009471 action Effects 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000000872 buffer Substances 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- DTETYCNJKAUROO-UHFFFAOYSA-N 4-methyl-1,3-oxazolidine-2,5-dione Chemical compound CC1NC(=O)OC1=O DTETYCNJKAUROO-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 108010013639 Peptidoglycan Proteins 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 229940024606 amino acid Drugs 0.000 description 2
- 235000001014 amino acid Nutrition 0.000 description 2
- 230000003115 biocidal effect Effects 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- 229960005190 phenylalanine Drugs 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- VIRHVJKBDQINKD-YOEHRIQHSA-N (2S)-2-[[(2S)-2-[(2-benzamidoacetyl)amino]-3-phenylpropanoyl]amino]propanoic acid Chemical compound C(C1=CC=CC=C1)(=O)NCC(=O)N[C@@H](CC1=CC=CC=C1)C(=O)N[C@@H](C)C(=O)O VIRHVJKBDQINKD-YOEHRIQHSA-N 0.000 description 1
- ODIGIKRIUKFKHP-UHFFFAOYSA-N (n-propan-2-yloxycarbonylanilino) acetate Chemical compound CC(C)OC(=O)N(OC(C)=O)C1=CC=CC=C1 ODIGIKRIUKFKHP-UHFFFAOYSA-N 0.000 description 1
- YOETUEMZNOLGDB-UHFFFAOYSA-N 2-methylpropyl carbonochloridate Chemical compound CC(C)COC(Cl)=O YOETUEMZNOLGDB-UHFFFAOYSA-N 0.000 description 1
- 241000194103 Bacillus pumilus Species 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- ZGUNAGUHMKGQNY-SSDOTTSWSA-N D-alpha-phenylglycine Chemical compound OC(=O)[C@H](N)C1=CC=CC=C1 ZGUNAGUHMKGQNY-SSDOTTSWSA-N 0.000 description 1
- 125000002435 L-phenylalanyl group Chemical group O=C([*])[C@](N([H])[H])([H])C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 229960003767 alanine Drugs 0.000 description 1
- 235000004279 alanine Nutrition 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 210000002421 cell wall Anatomy 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229940127089 cytotoxic agent Drugs 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 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
- 239000008363 phosphate buffer Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
- C07K1/14—Extraction; Separation; Purification
-
- 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/36—Compounds containing oxirane rings with hydrocarbon radicals, substituted by nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- General Chemical & Material Sciences (AREA)
- Biophysics (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Analytical Chemistry (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Genetics & Genomics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Priority Applications (13)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL1973164318A PL87546B1 (enrdf_load_stackoverflow) | 1973-07-26 | 1973-07-26 | |
| BE146631A BE817735A (fr) | 1973-07-26 | 1974-07-17 | Derives n-acyles de desalanyltetaine et leur procede de preparation |
| IN1604/CAL/74A IN140064B (enrdf_load_stackoverflow) | 1973-07-26 | 1974-07-18 | |
| CA205,149A CA1034567A (en) | 1973-07-26 | 1974-07-19 | Desalanyltetaine n-acyl derivatives and the method for their preparation |
| SE7409506A SE434158B (sv) | 1973-07-26 | 1974-07-22 | Forfarande for framstellning av n-acylderivat av desalanyltetain eller tetain |
| GB32334/74A GB1481881A (en) | 1973-07-26 | 1974-07-22 | Desalanyltetaine n-acyl derivatives and the method for their preparation |
| DE2435619A DE2435619A1 (de) | 1973-07-26 | 1974-07-24 | N-acyl-derivate des desalanyltetain und verfahren zu ihrer herstellung |
| HU74PO573A HU174054B (hu) | 1973-07-26 | 1974-07-24 | Sposob poluchenija n-acilirovannykh proizvodnykh dezalanil-tetaina |
| FR7425679A FR2245669B1 (enrdf_load_stackoverflow) | 1973-07-26 | 1974-07-24 | |
| CH1022674A CH602688A5 (enrdf_load_stackoverflow) | 1973-07-26 | 1974-07-24 | |
| JP8556474A JPS5652896B2 (enrdf_load_stackoverflow) | 1973-07-26 | 1974-07-25 | |
| SU7402048486A SU569282A3 (ru) | 1973-07-26 | 1974-07-25 | Способ получени -ацильных производных дезаланилтетаина |
| NL7410104.A NL159989C (nl) | 1973-07-26 | 1974-07-26 | Werkwijze voor het bereiden van tetainederivaten. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL1973164318A PL87546B1 (enrdf_load_stackoverflow) | 1973-07-26 | 1973-07-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL87546B1 true PL87546B1 (enrdf_load_stackoverflow) | 1976-07-31 |
Family
ID=19963606
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1973164318A PL87546B1 (enrdf_load_stackoverflow) | 1973-07-26 | 1973-07-26 |
Country Status (13)
-
1973
- 1973-07-26 PL PL1973164318A patent/PL87546B1/pl unknown
-
1974
- 1974-07-17 BE BE146631A patent/BE817735A/xx not_active IP Right Cessation
- 1974-07-18 IN IN1604/CAL/74A patent/IN140064B/en unknown
- 1974-07-19 CA CA205,149A patent/CA1034567A/en not_active Expired
- 1974-07-22 SE SE7409506A patent/SE434158B/xx unknown
- 1974-07-22 GB GB32334/74A patent/GB1481881A/en not_active Expired
- 1974-07-24 FR FR7425679A patent/FR2245669B1/fr not_active Expired
- 1974-07-24 CH CH1022674A patent/CH602688A5/xx not_active IP Right Cessation
- 1974-07-24 HU HU74PO573A patent/HU174054B/hu unknown
- 1974-07-24 DE DE2435619A patent/DE2435619A1/de active Granted
- 1974-07-25 JP JP8556474A patent/JPS5652896B2/ja not_active Expired
- 1974-07-25 SU SU7402048486A patent/SU569282A3/ru active
- 1974-07-26 NL NL7410104.A patent/NL159989C/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5652896B2 (enrdf_load_stackoverflow) | 1981-12-15 |
| CH602688A5 (enrdf_load_stackoverflow) | 1978-07-31 |
| DE2435619B2 (enrdf_load_stackoverflow) | 1979-05-10 |
| NL7410104A (nl) | 1975-01-28 |
| FR2245669A1 (enrdf_load_stackoverflow) | 1975-04-25 |
| NL159989C (nl) | 1979-09-17 |
| NL159989B (nl) | 1979-04-17 |
| CA1034567A (en) | 1978-07-11 |
| SE7409506L (enrdf_load_stackoverflow) | 1975-01-27 |
| SE434158B (sv) | 1984-07-09 |
| JPS5041801A (enrdf_load_stackoverflow) | 1975-04-16 |
| SU569282A3 (ru) | 1977-08-15 |
| HU174054B (hu) | 1979-10-28 |
| BE817735A (fr) | 1974-11-18 |
| FR2245669B1 (enrdf_load_stackoverflow) | 1977-06-24 |
| GB1481881A (en) | 1977-08-03 |
| DE2435619A1 (de) | 1975-02-27 |
| DE2435619C3 (enrdf_load_stackoverflow) | 1980-01-03 |
| IN140064B (enrdf_load_stackoverflow) | 1976-09-04 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Walzel et al. | Mechanism of alkaloid cyclopeptide synthesis in the ergot fungus Claviceps purpurea | |
| Wang et al. | Synthesis of characteristic Mycobacterium peptidoglycan (PGN) fragments utilizing with chemoenzymatic preparation of meso-diaminopimelic acid (DAP), and their modulation of innate immune responses | |
| Wong et al. | Enzymic synthesis of N-and O-linked glycopeptides | |
| EP0695759A2 (en) | Human cancer inhibitory pentapeptide methyl esters | |
| AU2009231118B2 (en) | Highly bridged peptides from actinomadura namibiensis | |
| AU2001275943B2 (en) | Derivatives of laspartomycin and preparation and use thereof | |
| Hwang et al. | Portage transport of sulfanilamide and sulfanilic acid | |
| US11149067B2 (en) | Tailored cyclodepsipeptides as potent non-covalent serine protease inhibitors | |
| AU2001275943A1 (en) | Derivatives of laspartomycin and preparation and use thereof | |
| JPH0344398A (ja) | 抗真菌抗生物質ｒ１０６誘導体 | |
| PL87546B1 (enrdf_load_stackoverflow) | ||
| Schweizer et al. | Synthesis of a galacto-configured C-ketoside-based γ-sugar-amino acid and its use in peptide coupling reactions | |
| KR100226305B1 (ko) | 폴리히드록시 시클로펜탄유도체, 그의 제조방법 및 그의 치료적용도 | |
| Kawai et al. | Studies on a new immunoactive peptide, FK-156 III. Structure elucidation | |
| EP0934076A4 (enrdf_load_stackoverflow) | ||
| EP0134563B1 (en) | Novel aminoglycoside compounds and their acid addition salts and process for production thereof | |
| Neumann et al. | Intramolecular acyl migration in adenosine derivatives. | |
| US20030027980A1 (en) | Process for preparing lipid ii | |
| CN117916250A (zh) | 空间位阻混合酸酐中间体参与的肽合成方法 | |
| US8981049B2 (en) | Aziridine mediated native chemical ligation | |
| Stoineva et al. | Chemical-enzymatic incorporation of D-amino acids into peptides: synthesis of diastereomeric (D-Ala2, D-Leu5) enkephalinamides | |
| EP1417223B1 (en) | Process for preparing lipid ii | |
| Matsuura et al. | Studies of Peptide Antibiotics. XVI. Analogs of Gramicidin S Containing β-Alanine in Place of L-Proline | |
| Kuroda et al. | FR-900148, A NEW ANTIBIOTIC II. STRUCTURE DETERMINATION OF FR-900148 | |
| Makisumi et al. | Studies of peptide antibiotics. XXV. Synthesis of an immediate precursor of gramicidin S |