NO851655L - Mikrobiologisk fremgangsmaate til fremstilling av antracyklin-derivater. - Google Patents
Mikrobiologisk fremgangsmaate til fremstilling av antracyklin-derivater.Info
- Publication number
- NO851655L NO851655L NO851655A NO851655A NO851655L NO 851655 L NO851655 L NO 851655L NO 851655 A NO851655 A NO 851655A NO 851655 A NO851655 A NO 851655A NO 851655 L NO851655 L NO 851655L
- Authority
- NO
- Norway
- Prior art keywords
- roa
- rod
- cina
- acu
- cytorhodin
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims description 13
- 238000000034 method Methods 0.000 title claims description 12
- 230000002906 microbiologic effect Effects 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 25
- 102000004316 Oxidoreductases Human genes 0.000 claims description 15
- 108090000854 Oxidoreductases Proteins 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 10
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 9
- 241001467544 Streptomyces galilaeus Species 0.000 claims description 8
- 241000187410 Streptomyces purpurascens Species 0.000 claims description 8
- 239000000706 filtrate Substances 0.000 claims description 7
- ATPYMFXOZQEWIG-LFRDXLMFSA-N (2s,5r,6s)-5,6-dihydroxy-2-methyloxan-3-one Chemical compound C[C@@H]1O[C@H](O)[C@H](O)CC1=O ATPYMFXOZQEWIG-LFRDXLMFSA-N 0.000 claims description 4
- 238000000605 extraction Methods 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 238000006911 enzymatic reaction Methods 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 150000002500 ions Chemical class 0.000 claims description 3
- 239000012429 reaction media Substances 0.000 claims description 3
- XXIHHRIZGBRENI-WDSKDSINSA-N L-rhodinose Chemical compound C[C@H](O)[C@@H](O)CCC=O XXIHHRIZGBRENI-WDSKDSINSA-N 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 41
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 34
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
- 239000000243 solution Substances 0.000 description 25
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 20
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
- 210000004027 cell Anatomy 0.000 description 15
- 239000000126 substance Substances 0.000 description 15
- 235000019439 ethyl acetate Nutrition 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 239000000872 buffer Substances 0.000 description 10
- 239000012071 phase Substances 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- 238000000862 absorption spectrum Methods 0.000 description 8
- 238000004128 high performance liquid chromatography Methods 0.000 description 8
- 239000007858 starting material Substances 0.000 description 8
- 229920001817 Agar Polymers 0.000 description 6
- AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 description 6
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 6
- 102000004190 Enzymes Human genes 0.000 description 6
- 108090000790 Enzymes Proteins 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000008272 agar Substances 0.000 description 6
- 229940088598 enzyme Drugs 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- 238000004809 thin layer chromatography Methods 0.000 description 6
- 229940045799 anthracyclines and related substance Drugs 0.000 description 5
- 229950006191 gluconic acid Drugs 0.000 description 5
- 238000011534 incubation Methods 0.000 description 5
- 229940099563 lactobionic acid Drugs 0.000 description 5
- 239000002609 medium Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 230000007306 turnover Effects 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 4
- RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- IQFYYKKMVGJFEH-XLPZGREQSA-N Thymidine Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CO)[C@@H](O)C1 IQFYYKKMVGJFEH-XLPZGREQSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 235000012208 gluconic acid Nutrition 0.000 description 4
- 238000002953 preparative HPLC Methods 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 229940009456 adriamycin Drugs 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 210000000170 cell membrane Anatomy 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 230000001085 cytostatic effect Effects 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 238000000855 fermentation Methods 0.000 description 3
- 230000004151 fermentation Effects 0.000 description 3
- 239000002054 inoculum Substances 0.000 description 3
- 208000032839 leukemia Diseases 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 229940104230 thymidine Drugs 0.000 description 3
- ZYECOAILUNWEAL-NUDFZHEQSA-N (4z)-4-[[2-methoxy-5-(phenylcarbamoyl)phenyl]hydrazinylidene]-n-(3-nitrophenyl)-3-oxonaphthalene-2-carboxamide Chemical compound COC1=CC=C(C(=O)NC=2C=CC=CC=2)C=C1N\N=C(C1=CC=CC=C1C=1)/C(=O)C=1C(=O)NC1=CC=CC([N+]([O-])=O)=C1 ZYECOAILUNWEAL-NUDFZHEQSA-N 0.000 description 2
- MWMZEHHNWIPABX-IHIFUPQISA-N (7s,9r,10r)-7-[(2r,4s,5s,6s)-4-(dimethylamino)-5-[5-(5-hydroxy-6-methyloxan-2-yl)oxy-6-methyloxan-2-yl]oxy-6-methyloxan-2-yl]oxy-10-[(4s,5s,6s)-4-(dimethylamino)-5-[5-(5-hydroxy-6-methyloxan-2-yl)oxy-6-methyloxan-2-yl]oxy-6-methyloxan-2-yl]oxy-9-ethyl-6,9 Chemical compound O([C@H]1[C@H](C[C@@H](O[C@H]1C)O[C@H]1C[C@]([C@@H](C2=C(O)C=3C(=O)C4=CC=CC=C4C(=O)C=3C(O)=C21)OC1O[C@@H](C)[C@@H](OC2OC(C)C(OC3OC(C)C(O)CC3)CC2)[C@H](C1)N(C)C)(O)CC)N(C)C)C(OC1C)CCC1OC1CCC(O)C(C)O1 MWMZEHHNWIPABX-IHIFUPQISA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- DWRXFEITVBNRMK-UHFFFAOYSA-N Beta-D-1-Arabinofuranosylthymine Natural products O=C1NC(=O)C(C)=CN1C1C(O)C(O)C(CO)O1 DWRXFEITVBNRMK-UHFFFAOYSA-N 0.000 description 2
- RGHNJXZEOKUKBD-SQOUGZDYSA-M D-gluconate Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O RGHNJXZEOKUKBD-SQOUGZDYSA-M 0.000 description 2
- 229910000831 Steel Inorganic materials 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 238000005273 aeration Methods 0.000 description 2
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 2
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 2
- 239000001166 ammonium sulphate Substances 0.000 description 2
- 235000011130 ammonium sulphate Nutrition 0.000 description 2
- IQFYYKKMVGJFEH-UHFFFAOYSA-N beta-L-thymidine Natural products O=C1NC(=O)C(C)=CN1C1OC(CO)C(O)C1 IQFYYKKMVGJFEH-UHFFFAOYSA-N 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 239000002274 desiccant Substances 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- 239000012737 fresh medium Substances 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 244000005700 microbiome Species 0.000 description 2
- 235000015097 nutrients Nutrition 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 239000004014 plasticizer Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 230000002285 radioactive effect Effects 0.000 description 2
- 239000010959 steel Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 229940086542 triethylamine Drugs 0.000 description 2
- QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 1
- UOQHWNPVNXSDDO-UHFFFAOYSA-N 3-bromoimidazo[1,2-a]pyridine-6-carbonitrile Chemical compound C1=CC(C#N)=CN2C(Br)=CN=C21 UOQHWNPVNXSDDO-UHFFFAOYSA-N 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 239000007832 Na2SO4 Substances 0.000 description 1
- 102000003992 Peroxidases Human genes 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 239000012980 RPMI-1640 medium Substances 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 241000187747 Streptomyces Species 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000008351 acetate buffer Substances 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 230000003698 anagen phase Effects 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 230000008033 biological extinction Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000022131 cell cycle Effects 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000005757 colony formation Effects 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000000824 cytostatic agent Substances 0.000 description 1
- 230000001472 cytotoxic effect Effects 0.000 description 1
- 229940079919 digestives enzyme preparation Drugs 0.000 description 1
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000002024 ethyl acetate extract Substances 0.000 description 1
- 238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 1
- 239000000174 gluconic acid Substances 0.000 description 1
- 230000012010 growth Effects 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- 229940050176 methyl chloride Drugs 0.000 description 1
- 238000013048 microbiological method Methods 0.000 description 1
- PJUIMOJAAPLTRJ-UHFFFAOYSA-N monothioglycerol Chemical compound OCC(O)CS PJUIMOJAAPLTRJ-UHFFFAOYSA-N 0.000 description 1
- AJDUTMFFZHIJEM-UHFFFAOYSA-N n-(9,10-dioxoanthracen-1-yl)-4-[4-[[4-[4-[(9,10-dioxoanthracen-1-yl)carbamoyl]phenyl]phenyl]diazenyl]phenyl]benzamide Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2NC(=O)C(C=C1)=CC=C1C(C=C1)=CC=C1N=NC(C=C1)=CC=C1C(C=C1)=CC=C1C(=O)NC1=CC=CC2=C1C(=O)C1=CC=CC=C1C2=O AJDUTMFFZHIJEM-UHFFFAOYSA-N 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 108040007629 peroxidase activity proteins Proteins 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000005245 sintering Methods 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 238000010257 thawing Methods 0.000 description 1
- 229940035024 thioglycerol Drugs 0.000 description 1
- 235000013619 trace mineral Nutrition 0.000 description 1
- 239000011573 trace mineral Substances 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000001043 yellow dye Substances 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
- C12P19/00—Preparation of compounds containing saccharide radicals
- C12P19/44—Preparation of O-glycosides, e.g. glucosides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/20—Carbocyclic rings
- C07H15/24—Condensed ring systems having three or more rings
- C07H15/252—Naphthacene radicals, e.g. daunomycins, adriamycins
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
- C12N1/00—Microorganisms, e.g. protozoa; Compositions thereof; Processes of propagating, maintaining or preserving microorganisms or compositions thereof; Processes of preparing or isolating a composition containing a microorganism; Culture media therefor
- C12N1/20—Bacteria; Culture media therefor
- C12N1/205—Bacterial isolates
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12R—INDEXING SCHEME ASSOCIATED WITH SUBCLASSES C12C - C12Q, RELATING TO MICROORGANISMS
- C12R2001/00—Microorganisms ; Processes using microorganisms
- C12R2001/01—Bacteria or Actinomycetales ; using bacteria or Actinomycetales
- C12R2001/465—Streptomyces
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Microbiology (AREA)
- General Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Molecular Biology (AREA)
- Medicinal Chemistry (AREA)
- Tropical Medicine & Parasitology (AREA)
- Virology (AREA)
- Biomedical Technology (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19843415544 DE3415544A1 (de) | 1984-04-26 | 1984-04-26 | Mikrobiologisches verfahren zur herstellung von anthracyclin-derivaten |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO851655L true NO851655L (no) | 1985-10-28 |
Family
ID=6234422
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO851655A NO851655L (no) | 1984-04-26 | 1985-04-25 | Mikrobiologisk fremgangsmaate til fremstilling av antracyklin-derivater. |
Country Status (11)
| Country | Link |
|---|---|
| KR (1) | KR920009515B1 (de) |
| AT (1) | AT388175B (de) |
| CA (1) | CA1247028A (de) |
| DE (1) | DE3415544A1 (de) |
| ES (1) | ES542523A0 (de) |
| FI (1) | FI851613L (de) |
| GR (1) | GR851003B (de) |
| HU (1) | HU195537B (de) |
| MX (1) | MX7305E (de) |
| NO (1) | NO851655L (de) |
| PT (1) | PT80357B (de) |
-
1984
- 1984-04-26 DE DE19843415544 patent/DE3415544A1/de not_active Withdrawn
-
1985
- 1985-04-19 HU HU851527A patent/HU195537B/hu unknown
- 1985-04-24 ES ES542523A patent/ES542523A0/es active Granted
- 1985-04-24 FI FI851613A patent/FI851613L/fi not_active Application Discontinuation
- 1985-04-24 CA CA000479936A patent/CA1247028A/en not_active Expired
- 1985-04-25 AT AT0124185A patent/AT388175B/de active
- 1985-04-25 GR GR851003A patent/GR851003B/el unknown
- 1985-04-25 KR KR1019850002800A patent/KR920009515B1/ko active IP Right Grant
- 1985-04-25 MX MX851153U patent/MX7305E/es unknown
- 1985-04-25 NO NO851655A patent/NO851655L/no unknown
- 1985-04-26 PT PT80357A patent/PT80357B/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| GR851003B (de) | 1985-11-25 |
| PT80357B (de) | 1987-02-11 |
| KR850007613A (ko) | 1985-12-07 |
| PT80357A (de) | 1985-05-01 |
| ATA124185A (de) | 1988-10-15 |
| HUT37818A (en) | 1986-02-28 |
| DE3415544A1 (de) | 1985-11-21 |
| ES8603576A1 (es) | 1985-12-16 |
| HU195537B (en) | 1988-05-30 |
| MX7305E (es) | 1988-04-29 |
| KR920009515B1 (ko) | 1992-10-17 |
| FI851613L (fi) | 1985-10-27 |
| ES542523A0 (es) | 1985-12-16 |
| FI851613A0 (fi) | 1985-04-24 |
| CA1247028A (en) | 1988-12-20 |
| AT388175B (de) | 1989-05-10 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| SU1151218A3 (ru) | Способ получени антибиотика-макролида | |
| NO160011B (no) | Mikrobiologisk fremgangsmaate for fremstilling av antracyklin-derivater. | |
| JP2792629B2 (ja) | 新規な１０員環ラクトンおよびその製造方法 | |
| NO135318B (de) | ||
| KR100311067B1 (ko) | 콜히치노이드화합물들을그와상응하는3-글리코실유도체로만드는생물학적변환과정 | |
| NO851655L (no) | Mikrobiologisk fremgangsmaate til fremstilling av antracyklin-derivater. | |
| NO336051B1 (no) | Biotransformasjon av colchicinoidforbindelser | |
| Furumai et al. | STUDIES ON THE BIOSYNTHESIS OF BASIC 16-MEMBERED MACROLIDE ANTIBIOTICS, PLATENOMYCINS. III PRODUCTION, ISOLATION AND STRUCTURES OF PLATENOLIDES I AND II | |
| US6372458B1 (en) | Process for the biotransformation of colchicone compounds into the correspondence 3-glycosyl derivatives | |
| KR100670413B1 (ko) | 루스쿠스 아쿨레아투스 스테로이드 배당체 유도체의제조방법 | |
| EP0083019A2 (de) | Verfahren zur Herstellung von aktiven Anthracyklinglykosiden, 4-deoxy-Aklacinomycin A und B, und deren pharmazeutische Zusammensetzungen | |
| US4001246A (en) | Derivatives of 24-methylene-14a-aza-d-homo-cholestadienes | |
| US4923403A (en) | Microbiological process for degradation of steroids | |
| Maatooq et al. | Microbial transformation of cucurbitacin E 2-O-β-D-glucopyranoside | |
| TW200525036A (en) | Microbial method for hydrolysis and oxidation of androst-5-ene and pregn-5-ene steroid esters | |
| KR970001001B1 (ko) | I-디옥시만노딜리마이신의 제법 | |
| DE3425357A1 (de) | 1-hydroxy-cytorhodine, ein mikrobiologisches verfahren zu ihrer herstellung und ihre verwendung als cytostatika | |
| US3780026A (en) | Biochemical aldosterone synthesis | |
| US3532714A (en) | Antifungal agents | |
| Albrecht et al. | Transformation of 12‐deoxycardenolids with Streptomyces purpurascens | |
| JPS63188695A (ja) | エリスロマイシンｂ誘導体およびその製造方法 | |
| EP0284358A1 (de) | Antitumor-Derivate, Verfahren zu ihrer Herstellung und pharmazeutische Zusammensetzungen, die sie enthalten | |
| JPH02257887A (ja) | ストレプトミセス属菌からの新規アングサイクリノンおよびその製造方法 | |
| HU204575B (en) | Process for producing 1-methyl-1,4-androstadiene-3,17-dion | |
| JPS6351395A (ja) | 抗生物質ｓｆ−２４１５物質およびその製造法 |