CA2378868A1 - Process for deacylation of lipodepsipeptides - Google Patents
Process for deacylation of lipodepsipeptides Download PDFInfo
- Publication number
- CA2378868A1 CA2378868A1 CA002378868A CA2378868A CA2378868A1 CA 2378868 A1 CA2378868 A1 CA 2378868A1 CA 002378868 A CA002378868 A CA 002378868A CA 2378868 A CA2378868 A CA 2378868A CA 2378868 A1 CA2378868 A1 CA 2378868A1
- Authority
- CA
- Canada
- Prior art keywords
- pseudomycin
- syringomycin
- nucleus
- syringae
- produce
- 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.)
- Abandoned
Links
- 238000000034 method Methods 0.000 title claims abstract description 28
- 230000020176 deacylation Effects 0.000 title description 13
- 238000005947 deacylation reaction Methods 0.000 title description 13
- 150000001875 compounds Chemical class 0.000 claims description 24
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- 102000004190 Enzymes Human genes 0.000 claims description 15
- 108010033876 pseudomycin A Proteins 0.000 claims description 15
- XDPWWEOIDYYUDN-HCEIJDMSSA-N 2-[(9z)-18-(4-aminobutyl)-15,24-bis(2-aminoethyl)-21-(carboxymethyl)-3-(2-chloro-1-hydroxyethyl)-27-(3,4-dihydroxytetradecanoylamino)-9-ethylidene-12-(1-hydroxyethyl)-2,5,8,11,14,17,20,23,26-nonaoxo-1-oxa-4,7,10,13,16,19,22,25-octazacyclooctacos-6-yl]-2-h Chemical compound CCCCCCCCCCC(O)C(O)CC(=O)NC1COC(=O)C(C(O)CCl)NC(=O)C(C(O)C(O)=O)NC(=O)\C(=C\C)NC(=O)C(C(C)O)NC(=O)C(CCN)NC(=O)C(CCCCN)NC(=O)C(CC(O)=O)NC(=O)C(CCN)NC1=O XDPWWEOIDYYUDN-HCEIJDMSSA-N 0.000 claims description 14
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- 238000004519 manufacturing process Methods 0.000 description 10
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- KDXKERNSBIXSRK-UHFFFAOYSA-N lysine Chemical compound NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 3
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- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical class OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 239000003570 air Substances 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000012062 aqueous buffer Substances 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 229960000271 arbutin Drugs 0.000 description 1
- 125000005228 aryl sulfonate group Chemical group 0.000 description 1
- CKLJMWTZIZZHCS-REOHCLBHSA-L aspartate group Chemical class N[C@@H](CC(=O)[O-])C(=O)[O-] CKLJMWTZIZZHCS-REOHCLBHSA-L 0.000 description 1
- 235000003704 aspartic acid Nutrition 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 1
- 230000000975 bioactive effect Effects 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 239000012472 biological sample Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-M bisulphate group Chemical group S([O-])(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
- 239000008366 buffered solution Substances 0.000 description 1
- MIOPJNTWMNEORI-UHFFFAOYSA-N camphorsulfonic acid Chemical class C1CC2(CS(O)(=O)=O)C(=O)CC1C2(C)C MIOPJNTWMNEORI-UHFFFAOYSA-N 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000002962 chemical mutagen Substances 0.000 description 1
- 150000001860 citric acid derivatives Chemical class 0.000 description 1
- 238000005094 computer simulation Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000002596 correlated effect Effects 0.000 description 1
- 238000012136 culture method Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 229960003964 deoxycholic acid Drugs 0.000 description 1
- 125000004990 dihydroxyalkyl group Chemical group 0.000 description 1
- UXGNZZKBCMGWAZ-UHFFFAOYSA-N dimethylformamide dmf Chemical compound CN(C)C=O.CN(C)C=O UXGNZZKBCMGWAZ-UHFFFAOYSA-N 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- FAUOJMHVEYMQQG-HVYQDZECSA-N echinocandin B Chemical compound C1([C@H](O)[C@@H](O)[C@H]2C(=O)N[C@H](C(=O)N3C[C@H](C)[C@H](O)[C@H]3C(=O)N[C@H](O)[C@H](O)C[C@@H](C(N[C@H](C(=O)N3C[C@H](O)C[C@H]3C(=O)N2)[C@@H](C)O)=O)NC(=O)CCCCCCC\C=C/C\C=C/CCCCC)[C@@H](C)O)=CC=C(O)C=C1 FAUOJMHVEYMQQG-HVYQDZECSA-N 0.000 description 1
- 108010062092 echinocandin B Proteins 0.000 description 1
- 210000003038 endothelium Anatomy 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 235000013922 glutamic acid Nutrition 0.000 description 1
- 239000004220 glutamic acid Substances 0.000 description 1
- 150000002315 glycerophosphates Chemical class 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000005020 hydroxyalkenyl group Chemical group 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 229960004125 ketoconazole Drugs 0.000 description 1
- 150000003893 lactate salts Chemical class 0.000 description 1
- 238000009630 liquid culture Methods 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 125000005341 metaphosphate group Chemical group 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000000329 molecular dynamics simulation Methods 0.000 description 1
- XWERQNZSJAIOTN-UHFFFAOYSA-N n-methyl-n-(1-nitroso-6-oxo-7h-purin-2-yl)nitramide Chemical compound O=C1N(N=O)C(N(C)[N+]([O-])=O)=NC2=C1NC=N2 XWERQNZSJAIOTN-UHFFFAOYSA-N 0.000 description 1
- 150000002814 niacins Chemical class 0.000 description 1
- 235000001968 nicotinic acid Nutrition 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000003891 oxalate salts Chemical class 0.000 description 1
- BJRNKVDFDLYUGJ-UHFFFAOYSA-N p-hydroxyphenyl beta-D-alloside Natural products OC1C(O)C(O)C(CO)OC1OC1=CC=C(O)C=C1 BJRNKVDFDLYUGJ-UHFFFAOYSA-N 0.000 description 1
- 150000002942 palmitic acid derivatives Chemical class 0.000 description 1
- 239000008063 pharmaceutical solvent Substances 0.000 description 1
- 231100000208 phytotoxic Toxicity 0.000 description 1
- 230000000885 phytotoxic effect Effects 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical class OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
- 125000005547 pivalate group Chemical group 0.000 description 1
- 229920001184 polypeptide Polymers 0.000 description 1
- 229910000160 potassium phosphate Inorganic materials 0.000 description 1
- 235000011009 potassium phosphates Nutrition 0.000 description 1
- 239000001965 potato dextrose agar Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 235000018102 proteins Nutrition 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 125000003607 serino group Chemical group [H]N([H])[C@]([H])(C(=O)[*])C(O[H])([H])[H] 0.000 description 1
- 238000002741 site-directed mutagenesis Methods 0.000 description 1
- FHHPUSMSKHSNKW-SMOYURAASA-M sodium deoxycholate Chemical compound [Na+].C([C@H]1CC2)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC([O-])=O)C)[C@@]2(C)[C@@H](O)C1 FHHPUSMSKHSNKW-SMOYURAASA-M 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 150000003890 succinate salts Chemical class 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical class [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 229930185586 syringostatin Natural products 0.000 description 1
- 229930194835 syringotoxin Natural products 0.000 description 1
- 150000003567 thiocyanates Chemical class 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 230000001131 transforming effect Effects 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
- C07K7/64—Cyclic peptides containing only normal peptide links
-
- 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
- A61P31/10—Antimycotics
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biophysics (AREA)
- Biochemistry (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Peptides Or Proteins (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US14396899P | 1999-07-15 | 1999-07-15 | |
| US60/143,968 | 1999-07-15 | ||
| PCT/US2000/015018 WO2001005815A1 (en) | 1999-07-15 | 2000-06-08 | Process for deacylation of lipodepsipeptides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2378868A1 true CA2378868A1 (en) | 2001-01-25 |
Family
ID=22506494
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002378868A Abandoned CA2378868A1 (en) | 1999-07-15 | 2000-06-08 | Process for deacylation of lipodepsipeptides |
Country Status (11)
| Country | Link |
|---|---|
| EP (1) | EP1198471A1 (es) |
| JP (1) | JP2003505042A (es) |
| CN (1) | CN1361791A (es) |
| AU (1) | AU5310600A (es) |
| BR (1) | BR0012481A (es) |
| CA (1) | CA2378868A1 (es) |
| EA (1) | EA200200162A1 (es) |
| HU (1) | HUP0202315A2 (es) |
| MX (1) | MXPA02000458A (es) |
| NO (1) | NO20020183L (es) |
| WO (1) | WO2001005815A1 (es) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002066499A1 (fr) | 2001-02-19 | 2002-08-29 | Takara Bio Inc. | Peptide cyclique |
| DE10335584B4 (de) * | 2003-07-31 | 2006-06-29 | Philipps-Universität Marburg | Verfahren zur Herstellung zyklischer Moleküle |
| US20060004185A1 (en) * | 2004-07-01 | 2006-01-05 | Leese Richard A | Peptide antibiotics and peptide intermediates for their prepartion |
| DE102004060750A1 (de) * | 2004-12-15 | 2006-07-13 | Sanofi-Aventis Deutschland Gmbh | Verfahren zur Deacylierung von Lipopeptiden |
| NZ593892A (en) | 2008-12-23 | 2013-11-29 | Biosource Pharm Inc | Antibiotic compositions for the treatment of gram negative infections |
| US8415307B1 (en) | 2010-06-23 | 2013-04-09 | Biosource Pharm, Inc. | Antibiotic compositions for the treatment of gram negative infections |
| WO2014044803A1 (en) * | 2012-09-24 | 2014-03-27 | Dsm Sinochem Pharmaceuticals Netherlands B.V. | Method for producing a cyclic peptide |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK0460882T3 (da) * | 1990-06-07 | 1996-08-26 | Lilly Co Eli | Lipopeptiddeacylase |
-
2000
- 2000-06-08 WO PCT/US2000/015018 patent/WO2001005815A1/en not_active Application Discontinuation
- 2000-06-08 AU AU53106/00A patent/AU5310600A/en not_active Abandoned
- 2000-06-08 JP JP2001511472A patent/JP2003505042A/ja not_active Withdrawn
- 2000-06-08 CA CA002378868A patent/CA2378868A1/en not_active Abandoned
- 2000-06-08 EA EA200200162A patent/EA200200162A1/ru unknown
- 2000-06-08 CN CN00810417A patent/CN1361791A/zh active Pending
- 2000-06-08 MX MXPA02000458A patent/MXPA02000458A/es unknown
- 2000-06-08 BR BR0012481-8A patent/BR0012481A/pt not_active Application Discontinuation
- 2000-06-08 HU HU0202315A patent/HUP0202315A2/hu unknown
- 2000-06-08 EP EP00938006A patent/EP1198471A1/en not_active Withdrawn
-
2002
- 2002-01-14 NO NO20020183A patent/NO20020183L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| EP1198471A1 (en) | 2002-04-24 |
| AU5310600A (en) | 2001-02-05 |
| JP2003505042A (ja) | 2003-02-12 |
| NO20020183D0 (no) | 2002-01-14 |
| HUP0202315A2 (en) | 2002-10-28 |
| CN1361791A (zh) | 2002-07-31 |
| EA200200162A1 (ru) | 2002-06-27 |
| BR0012481A (pt) | 2002-04-02 |
| WO2001005815A1 (en) | 2001-01-25 |
| MXPA02000458A (es) | 2002-07-02 |
| NO20020183L (no) | 2002-03-13 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |