CA1220746A - Luzopeptin e.sub.2 - Google Patents
Luzopeptin e.sub.2Info
- Publication number
- CA1220746A CA1220746A CA000446122A CA446122A CA1220746A CA 1220746 A CA1220746 A CA 1220746A CA 000446122 A CA000446122 A CA 000446122A CA 446122 A CA446122 A CA 446122A CA 1220746 A CA1220746 A CA 1220746A
- Authority
- CA
- Canada
- Prior art keywords
- luzopeptin
- methionine
- cysteine
- antibiotic
- methyl
- 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.)
- Expired
Links
- 229930190572 Luzopeptin Natural products 0.000 title description 13
- KEKNHSVGJZJNFK-UHFFFAOYSA-N luzopeptin Chemical compound OC1=CC2=CC(OC)=CC=C2N=C1C(=O)NC(C(N1N=CCC(O)C1C(=O)NCC(=O)N(C)CC(=O)N(C)C(C(=O)OC1)C(C)(C)O)=O)COC(=O)C(C(C)(C)O)N(C)C(=O)CN(C)C(=O)CNC(=O)C2C(O)CC=NN2C(=O)C1NC(=O)C1=NC2=CC=C(OC)C=C2C=C1O KEKNHSVGJZJNFK-UHFFFAOYSA-N 0.000 title description 11
- XOMHYSFBTSQDMS-UHFFFAOYSA-N Luzopeptin E2 Natural products OC1=CC2=CC(OC)=CC=C2N=C1C(=O)NC(C(N1N=CCCC1C(=O)NCC(=O)N(C)CC(=O)N(C)C(C(=O)OC1)C(C)(C)O)=O)COC(=O)C(C(C)(C)O)N(C)C(=O)CN(C)C(=O)CNC(=O)C2CCC=NN2C(=O)C1NC(=O)C1=NC2=CC=C(OC)C=C2C=C1O XOMHYSFBTSQDMS-UHFFFAOYSA-N 0.000 claims abstract description 61
- 238000000855 fermentation Methods 0.000 claims abstract description 19
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
- IDIDJDIHTAOVLG-VKHMYHEASA-N S-methylcysteine Chemical compound CSC[C@H](N)C(O)=O IDIDJDIHTAOVLG-VKHMYHEASA-N 0.000 claims description 10
- FFEARJCKVFRZRR-UHFFFAOYSA-N methionine Chemical compound CSCCC(N)C(O)=O FFEARJCKVFRZRR-UHFFFAOYSA-N 0.000 claims description 9
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- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 claims description 4
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- QXOHLNCNYLGICT-YFKPBYRVSA-N Met-Gly Chemical compound CSCC[C@H](N)C(=O)NCC(O)=O QXOHLNCNYLGICT-YFKPBYRVSA-N 0.000 claims description 2
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- HIWMCVYLBVFQQN-VBOHDVKSSA-N luzopeptin b Chemical compound C([C@H](C(N1N=CC[C@H](O)[C@H]1C(=O)NCC(=O)N(C)CC(=O)N(C)[C@H](C(=O)OC1)C(C)(C)O)=O)NC(=O)C2=NC3=CC=C(C=C3C=C2O)OC)OC(=O)[C@H](C(C)(C)O)N(C)C(=O)CN(C)C(=O)CNC(=O)[C@@H]2[C@@H](OC(C)=O)CC=NN2C(=O)[C@@H]1NC(=O)C1=NC2=CC=C(OC)C=C2C=C1O HIWMCVYLBVFQQN-VBOHDVKSSA-N 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 235000013379 molasses Nutrition 0.000 description 1
- 229940055036 mycobacterium phlei Drugs 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 235000019319 peptone Nutrition 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229920001184 polypeptide Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 239000003531 protein hydrolysate Substances 0.000 description 1
- 229940007042 proteus vulgaris Drugs 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 229910052682 stishovite Inorganic materials 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- YWYZEGXAUVWDED-UHFFFAOYSA-N triammonium citrate Chemical compound [NH4+].[NH4+].[NH4+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O YWYZEGXAUVWDED-UHFFFAOYSA-N 0.000 description 1
- 229910052905 tridymite Inorganic materials 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P21/00—Preparation of peptides or proteins
- C12P21/02—Preparation of peptides or proteins having a known sequence of two or more amino acids, e.g. glutathione
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
- C07K7/04—Linear peptides containing only normal peptide links
- C07K7/06—Linear peptides containing only normal peptide links having 5 to 11 amino acids
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Zoology (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- Wood Science & Technology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Biochemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Biotechnology (AREA)
- Biophysics (AREA)
- Microbiology (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
- Micro-Organisms Or Cultivation Processes Thereof (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US46257783A | 1983-01-31 | 1983-01-31 | |
| US462,577 | 1983-01-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1220746A true CA1220746A (en) | 1987-04-21 |
Family
ID=23836950
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000446122A Expired CA1220746A (en) | 1983-01-31 | 1984-01-26 | Luzopeptin e.sub.2 |
Country Status (15)
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5643871A (en) * | 1993-11-23 | 1997-07-01 | Bristol-Meyers Squibb Company | Antitumor antibiotics |
| GB2294265A (en) * | 1994-10-20 | 1996-04-24 | Merck & Co Inc | Cyclic depsipeptides obtained from Actinomycete sp. |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2050384B (en) * | 1979-04-02 | 1983-04-07 | Bristol Myers Co | Antitumor antibacterial agents |
-
1984
- 1984-01-24 AU AU23721/84A patent/AU566569B2/en not_active Ceased
- 1984-01-26 NL NL8400237A patent/NL8400237A/nl not_active Application Discontinuation
- 1984-01-26 CA CA000446122A patent/CA1220746A/en not_active Expired
- 1984-01-26 GR GR73628A patent/GR81749B/el unknown
- 1984-01-26 ZA ZA84613A patent/ZA84613B/xx unknown
- 1984-01-27 IT IT19348/84A patent/IT1175927B/it active
- 1984-01-28 KR KR1019840000383A patent/KR880001638B1/ko not_active Expired
- 1984-01-30 FR FR8401402A patent/FR2540116B1/fr not_active Expired
- 1984-01-30 GB GB08402410A patent/GB2134119B/en not_active Expired
- 1984-01-30 DE DE19843403125 patent/DE3403125A1/de not_active Withdrawn
- 1984-01-30 CH CH419/84A patent/CH663415A5/de not_active IP Right Cessation
- 1984-01-30 SE SE8400450A patent/SE464582B/sv not_active IP Right Cessation
- 1984-01-31 BE BE0/212317A patent/BE898807A/fr not_active IP Right Cessation
- 1984-01-31 JP JP59014543A patent/JPH0645638B2/ja not_active Expired - Lifetime
-
1988
- 1988-12-30 MY MY15/88A patent/MY8800015A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| GB2134119A (en) | 1984-08-08 |
| SE8400450D0 (sv) | 1984-01-30 |
| KR880001638B1 (ko) | 1988-09-03 |
| SE8400450L (sv) | 1984-08-01 |
| IT1175927B (it) | 1987-08-12 |
| GB2134119B (en) | 1986-04-30 |
| JPH0645638B2 (ja) | 1994-06-15 |
| GR81749B (enrdf_load_stackoverflow) | 1984-12-12 |
| IT8419348A0 (it) | 1984-01-27 |
| AU566569B2 (en) | 1987-10-22 |
| FR2540116A1 (fr) | 1984-08-03 |
| BE898807A (fr) | 1984-07-31 |
| JPS59173091A (ja) | 1984-09-29 |
| FR2540116B1 (fr) | 1989-08-18 |
| MY8800015A (en) | 1988-12-31 |
| DE3403125A1 (de) | 1984-10-31 |
| CH663415A5 (de) | 1987-12-15 |
| ZA84613B (en) | 1984-09-26 |
| SE464582B (sv) | 1991-05-13 |
| NL8400237A (nl) | 1984-08-16 |
| GB8402410D0 (en) | 1984-02-29 |
| KR840007106A (ko) | 1984-12-05 |
| AU2372184A (en) | 1984-08-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |