DE2435619A1 - N-acyl-derivate des desalanyltetain und verfahren zu ihrer herstellung - Google Patents
N-acyl-derivate des desalanyltetain und verfahren zu ihrer herstellungInfo
- Publication number
- DE2435619A1 DE2435619A1 DE2435619A DE2435619A DE2435619A1 DE 2435619 A1 DE2435619 A1 DE 2435619A1 DE 2435619 A DE2435619 A DE 2435619A DE 2435619 A DE2435619 A DE 2435619A DE 2435619 A1 DE2435619 A1 DE 2435619A1
- Authority
- DE
- Germany
- Prior art keywords
- tetaine
- desalanyl
- derivatives
- group
- tetain
- 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.)
- Granted
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 8
- 238000000034 method Methods 0.000 title description 10
- 230000008569 process Effects 0.000 title description 7
- 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 47
- 108700023668 bacilysin Proteins 0.000 claims description 47
- XFOUAXMJRHNTOP-UHFFFAOYSA-N Bacilysin Natural products CC(N)C(=O)NC(C(O)=O)CC1CCC(=O)C2OC12 XFOUAXMJRHNTOP-UHFFFAOYSA-N 0.000 claims description 13
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 9
- -1 N-protected amino Chemical class 0.000 claims description 4
- 102000004196 processed proteins & peptides Human genes 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- 239000012467 final product Substances 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims 1
- 150000001412 amines Chemical group 0.000 claims 1
- 125000006239 protecting group Chemical group 0.000 claims 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 9
- 239000000047 product Substances 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- 102000004190 Enzymes Human genes 0.000 description 5
- 108090000790 Enzymes Proteins 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- DTETYCNJKAUROO-UHFFFAOYSA-N 4-methyl-1,3-oxazolidine-2,5-dione Chemical compound CC1NC(=O)OC1=O DTETYCNJKAUROO-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000000872 buffer Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 229940024606 amino acid Drugs 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 2
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 229960003767 alanine Drugs 0.000 description 2
- 235000001014 amino acid Nutrition 0.000 description 2
- 230000003115 biocidal effect Effects 0.000 description 2
- 244000005700 microbiome Species 0.000 description 2
- 239000002244 precipitate Substances 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
- GQBIVYSGPXCELZ-QMMMGPOBSA-N (4s)-4-benzyl-1,3-oxazolidine-2,5-dione Chemical compound O=C1OC(=O)N[C@H]1CC1=CC=CC=C1 GQBIVYSGPXCELZ-QMMMGPOBSA-N 0.000 description 1
- 241000194103 Bacillus pumilus Species 0.000 description 1
- QNAYBMKLOCPYGJ-UHFFFAOYSA-N D-alpha-Ala Natural products CC([NH3+])C([O-])=O QNAYBMKLOCPYGJ-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- QNAYBMKLOCPYGJ-UWTATZPHSA-N L-Alanine Natural products C[C@@H](N)C(O)=O QNAYBMKLOCPYGJ-UWTATZPHSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- MNLRQHMNZILYPY-MDMHTWEWSA-N N-acetyl-alpha-D-muramic acid Chemical group OC(=O)[C@@H](C)O[C@H]1[C@H](O)[C@@H](CO)O[C@H](O)[C@@H]1NC(C)=O MNLRQHMNZILYPY-MDMHTWEWSA-N 0.000 description 1
- 108010013639 Peptidoglycan Proteins 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 235000004279 alanine Nutrition 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 150000001721 carbon Chemical class 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 229940044683 chemotherapy drug Drugs 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000003795 desorption Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 125000003630 glycyl group Chemical group [H]N([H])C([H])([H])C(*)=O 0.000 description 1
- 150000004678 hydrides Chemical class 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
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000008176 lyophilized powder Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 238000004816 paper chromatography Methods 0.000 description 1
- 229960005190 phenylalanine Drugs 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000000758 substrate Substances 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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL1973164318A PL87546B1 (enrdf_load_stackoverflow) | 1973-07-26 | 1973-07-26 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2435619A1 true DE2435619A1 (de) | 1975-02-27 |
| DE2435619B2 DE2435619B2 (enrdf_load_stackoverflow) | 1979-05-10 |
| DE2435619C3 DE2435619C3 (enrdf_load_stackoverflow) | 1980-01-03 |
Family
ID=19963606
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2435619A Granted DE2435619A1 (de) | 1973-07-26 | 1974-07-24 | N-acyl-derivate des desalanyltetain und verfahren zu ihrer herstellung |
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 |
| DE2435619C3 (enrdf_load_stackoverflow) | 1980-01-03 |
| PL87546B1 (enrdf_load_stackoverflow) | 1976-07-31 |
| IN140064B (enrdf_load_stackoverflow) | 1976-09-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| 8339 | Ceased/non-payment of the annual fee |