HU190680B - Process for preparing 6''-0-carbamoyl-tobramycin microbiologically - Google Patents
Process for preparing 6''-0-carbamoyl-tobramycin microbiologically Download PDFInfo
- Publication number
- HU190680B HU190680B HU813954A HU395481A HU190680B HU 190680 B HU190680 B HU 190680B HU 813954 A HU813954 A HU 813954A HU 395481 A HU395481 A HU 395481A HU 190680 B HU190680 B HU 190680B
- Authority
- HU
- Hungary
- Prior art keywords
- nebramycin
- mng
- tobramycin
- carbamoyl
- strain
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title description 4
- 238000000855 fermentation Methods 0.000 claims abstract description 29
- 230000004151 fermentation Effects 0.000 claims abstract description 29
- YPPFEJHOHNPKLT-PBSUHMDJSA-N nebramycin 5' Chemical compound N[C@@H]1C[C@H](O)[C@@H](CN)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](N)[C@H](O)[C@@H](COC(N)=O)O2)O)[C@H](N)C[C@@H]1N YPPFEJHOHNPKLT-PBSUHMDJSA-N 0.000 claims abstract description 22
- YPPFEJHOHNPKLT-UHFFFAOYSA-N Cuauhtemon-3-(2,3-epoxy-2,3-dihydroangelicat Natural products NC1CC(O)C(CN)OC1OC1C(O)C(OC2C(C(N)C(O)C(COC(N)=O)O2)O)C(N)CC1N YPPFEJHOHNPKLT-UHFFFAOYSA-N 0.000 claims abstract description 21
- SQJLXMDBYVXCEL-UHFFFAOYSA-N nebramycin 5' Natural products C1CC(C)=CCCC(=C)C2COC(=O)C(=CCC=C(C)C)C21 SQJLXMDBYVXCEL-UHFFFAOYSA-N 0.000 claims abstract description 21
- 235000010633 broth Nutrition 0.000 claims abstract description 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 10
- 241000187178 Streptoalloteichus tenebrarius Species 0.000 claims abstract description 10
- 238000000034 method Methods 0.000 claims abstract description 10
- 241001465754 Metazoa Species 0.000 claims abstract description 6
- 239000011573 trace mineral Substances 0.000 claims abstract description 6
- 235000013619 trace mineral Nutrition 0.000 claims abstract description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 4
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 4
- 150000003839 salts Chemical class 0.000 claims abstract description 4
- 238000002360 preparation method Methods 0.000 claims description 6
- 239000000499 gel Substances 0.000 claims description 3
- 235000015112 vegetable and seed oil Nutrition 0.000 claims description 3
- 239000008158 vegetable oil Substances 0.000 claims description 2
- 239000000203 mixture Substances 0.000 abstract description 17
- XCSTZNJIQFIVPE-FQSMHNGLSA-N Nebramycin IV Chemical compound N[C@@H]1[C@@H](O)[C@H](O)[C@@H](CN)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](N)[C@H](O)[C@@H](COC(N)=O)O2)O)[C@H](N)C[C@@H]1N XCSTZNJIQFIVPE-FQSMHNGLSA-N 0.000 abstract description 13
- 230000003115 biocidal effect Effects 0.000 abstract description 13
- NLVFBUXFDBBNBW-PBSUHMDJSA-N tobramycin Chemical compound N[C@@H]1C[C@H](O)[C@@H](CN)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O2)O)[C@H](N)C[C@@H]1N NLVFBUXFDBBNBW-PBSUHMDJSA-N 0.000 abstract description 11
- 239000003925 fat Substances 0.000 abstract description 4
- 239000003921 oil Substances 0.000 abstract description 4
- 229950011272 nebramycin Drugs 0.000 abstract description 3
- XZNUGFQTQHRASN-XQENGBIVSA-N apramycin Chemical compound O([C@H]1O[C@@H]2[C@H](O)[C@@H]([C@H](O[C@H]2C[C@H]1N)O[C@@H]1[C@@H]([C@@H](O)[C@H](N)[C@@H](CO)O1)O)NC)[C@@H]1[C@@H](N)C[C@@H](N)[C@H](O)[C@H]1O XZNUGFQTQHRASN-XQENGBIVSA-N 0.000 abstract description 2
- 229950006334 apramycin Drugs 0.000 abstract description 2
- 239000002609 medium Substances 0.000 description 21
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 229960000707 tobramycin Drugs 0.000 description 9
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 8
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 8
- 244000005700 microbiome Species 0.000 description 8
- 239000002054 inoculum Substances 0.000 description 7
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- 230000001851 biosynthetic effect Effects 0.000 description 6
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 5
- 235000019482 Palm oil Nutrition 0.000 description 5
- 239000000908 ammonium hydroxide Substances 0.000 description 5
- 239000008103 glucose Substances 0.000 description 5
- 239000002540 palm oil Substances 0.000 description 5
- 229920001817 Agar Polymers 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000008272 agar Substances 0.000 description 4
- 235000019270 ammonium chloride Nutrition 0.000 description 4
- 239000003242 anti bacterial agent Substances 0.000 description 4
- 229960001192 bekanamycin Drugs 0.000 description 4
- 229910000019 calcium carbonate Inorganic materials 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 235000021388 linseed oil Nutrition 0.000 description 4
- 239000000944 linseed oil Substances 0.000 description 4
- 235000012054 meals Nutrition 0.000 description 4
- PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 108010076119 Caseins Proteins 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 239000005018 casein Substances 0.000 description 3
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 3
- 235000021240 caseins Nutrition 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- ZMMJGEGLRURXTF-UHFFFAOYSA-N ethidium bromide Chemical compound [Br-].C12=CC(N)=CC=C2C2=CC=C(N)C=C2[N+](CC)=C1C1=CC=CC=C1 ZMMJGEGLRURXTF-UHFFFAOYSA-N 0.000 description 3
- 229960005542 ethidium bromide Drugs 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 238000002955 isolation Methods 0.000 description 3
- 229930182824 kanamycin B Natural products 0.000 description 3
- SKKLOUVUUNMCJE-FQSMHNGLSA-N kanamycin B Chemical compound N[C@@H]1[C@@H](O)[C@H](O)[C@@H](CN)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O2)O)[C@H](N)C[C@@H]1N SKKLOUVUUNMCJE-FQSMHNGLSA-N 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- WRUGWIBCXHJTDG-UHFFFAOYSA-L magnesium sulfate heptahydrate Chemical compound O.O.O.O.O.O.O.[Mg+2].[O-]S([O-])(=O)=O WRUGWIBCXHJTDG-UHFFFAOYSA-L 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 230000001954 sterilising effect Effects 0.000 description 3
- 238000004659 sterilization and disinfection Methods 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 229940088710 antibiotic agent Drugs 0.000 description 2
- 239000004599 antimicrobial Substances 0.000 description 2
- 229920001429 chelating resin Polymers 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000002512 chemotherapy Methods 0.000 description 2
- QGUAJWGNOXCYJF-UHFFFAOYSA-N cobalt dinitrate hexahydrate Chemical compound O.O.O.O.O.O.[Co+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O QGUAJWGNOXCYJF-UHFFFAOYSA-N 0.000 description 2
- 239000000356 contaminant Substances 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 235000019197 fats Nutrition 0.000 description 2
- 239000001963 growth medium Substances 0.000 description 2
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- 229920005989 resin Polymers 0.000 description 2
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- 238000003756 stirring Methods 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- 235000019871 vegetable fat Nutrition 0.000 description 2
- YZEUHQHUFTYLPH-UHFFFAOYSA-N 2-nitroimidazole Chemical compound [O-][N+](=O)C1=NC=CN1 YZEUHQHUFTYLPH-UHFFFAOYSA-N 0.000 description 1
- 208000031295 Animal disease Diseases 0.000 description 1
- 235000017060 Arachis glabrata Nutrition 0.000 description 1
- 244000105624 Arachis hypogaea Species 0.000 description 1
- 235000010777 Arachis hypogaea Nutrition 0.000 description 1
- 235000018262 Arachis monticola Nutrition 0.000 description 1
- 244000063299 Bacillus subtilis Species 0.000 description 1
- 235000014469 Bacillus subtilis Nutrition 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
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- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 1
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 1
- 241001026509 Kata Species 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 239000001888 Peptone Substances 0.000 description 1
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- 235000019484 Rapeseed oil Nutrition 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 241000203644 Streptoalloteichus hindustanus Species 0.000 description 1
- 241000187747 Streptomyces Species 0.000 description 1
- 235000019486 Sunflower oil Nutrition 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 238000005273 aeration Methods 0.000 description 1
- 238000010564 aerobic fermentation Methods 0.000 description 1
- 235000001014 amino acid Nutrition 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 239000001166 ammonium sulphate Substances 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 239000010775 animal oil Substances 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000012474 bioautography Methods 0.000 description 1
- 239000003139 biocide Substances 0.000 description 1
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- 229940041514 candida albicans extract Drugs 0.000 description 1
- 108010079058 casein hydrolysate Proteins 0.000 description 1
- 238000011210 chromatographic step Methods 0.000 description 1
- GFHNAMRJFCEERV-UHFFFAOYSA-L cobalt chloride hexahydrate Chemical compound O.O.O.O.O.O.[Cl-].[Cl-].[Co+2] GFHNAMRJFCEERV-UHFFFAOYSA-L 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
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- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
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- 239000000706 filtrate Substances 0.000 description 1
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- 239000007789 gas Substances 0.000 description 1
- 230000002068 genetic effect Effects 0.000 description 1
- 235000013922 glutamic acid Nutrition 0.000 description 1
- 239000004220 glutamic acid Substances 0.000 description 1
- 238000002513 implantation Methods 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 238000009630 liquid culture Methods 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- 230000035772 mutation Effects 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 238000012803 optimization experiment Methods 0.000 description 1
- 125000001477 organic nitrogen group Chemical group 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 235000020232 peanut Nutrition 0.000 description 1
- 235000019319 peptone Nutrition 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 230000005180 public health Effects 0.000 description 1
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- 239000000725 suspension Substances 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 238000007669 thermal treatment Methods 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000012138 yeast extract Substances 0.000 description 1
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 1
- 229960001763 zinc sulfate Drugs 0.000 description 1
- 229910000368 zinc sulfate Inorganic materials 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
- C12P19/46—Preparation of O-glycosides, e.g. glucosides having an oxygen atom of the saccharide radical bound to a cyclohexyl radical, e.g. kasugamycin
- C12P19/48—Preparation of O-glycosides, e.g. glucosides having an oxygen atom of the saccharide radical bound to a cyclohexyl radical, e.g. kasugamycin the cyclohexyl radical being substituted by two or more nitrogen atoms, e.g. destomycin, neamin
- C12P19/485—Having two saccharide radicals bound through only oxygen to non-adjacent ring carbons of the cyclohexyl radical, e.g. gentamycin, kanamycin, sisomycin, verdamycin, mutamycin, tobramycin, nebramycin, antibiotics 66-40B, 66-40D, XK-62-2, 66-40, G-418, G-52
-
- 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
- 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
- C12P19/46—Preparation of O-glycosides, e.g. glucosides having an oxygen atom of the saccharide radical bound to a cyclohexyl radical, e.g. kasugamycin
- C12P19/48—Preparation of O-glycosides, e.g. glucosides having an oxygen atom of the saccharide radical bound to a cyclohexyl radical, e.g. kasugamycin the cyclohexyl radical being substituted by two or more nitrogen atoms, e.g. destomycin, neamin
- C12P19/50—Preparation of O-glycosides, e.g. glucosides having an oxygen atom of the saccharide radical bound to a cyclohexyl radical, e.g. kasugamycin the cyclohexyl radical being substituted by two or more nitrogen atoms, e.g. destomycin, neamin having two saccharide radicals bound through only oxygen to adjacent ring carbon atoms of the cyclohexyl radical, e.g. ambutyrosin, ribostamycin
-
- 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)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Biotechnology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- Microbiology (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Biomedical Technology (AREA)
- Virology (AREA)
- Tropical Medicine & Parasitology (AREA)
- Medicinal Chemistry (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Micro-Organisms Or Cultivation Processes Thereof (AREA)
Priority Applications (11)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU813954A HU190680B (en) | 1981-12-28 | 1981-12-28 | Process for preparing 6''-0-carbamoyl-tobramycin microbiologically |
| BE1/10669A BE895455A (fr) | 1981-12-28 | 1982-12-23 | Procede microbiologique pour preparer de la nebramycine-2, de la nebramycine-5' et de la nebramycine-4 |
| CH7558/82A CH657374A5 (de) | 1981-12-28 | 1982-12-27 | Verfahren zur mikrobiologischen herstellung von nebramycin-5'. |
| CH3108/85A CH658072A5 (de) | 1981-12-28 | 1982-12-27 | Verfahren zur mikrobiologischen herstellung von nebramycin-2, nebramycin-5' und nebramycin-4. |
| FR8221803A FR2519023B1 (fr) | 1981-12-28 | 1982-12-27 | Procede microbiologique pour preparer de la nebramycine-2, de la nebramycine-5' et de la nebramycine-4 |
| NL8205011A NL8205011A (nl) | 1981-12-28 | 1982-12-28 | Microbiologische werkwijze voor de bereiding van nebramycine-2, nebramycine-5' en nebramycine-4. |
| AT0470482A AT379171B (de) | 1981-12-28 | 1982-12-28 | Verfahren zur mikrobiologischen herstellung von nebramycin-5' |
| DE19823248420 DE3248420A1 (de) | 1981-12-28 | 1982-12-28 | Verfahren zur mikrobiologischen herstellung von gaerbruehen, die entweder nahezu ausschliesslich nebramycin-5' oder ein gemisch von nebramycin-2 und nebramicyn-5' in einem beliebigen im voraus festgesetzten verhaeltnis und nebramycin-4 enthalten und in diesem verwendbarer mikroorganismusstamm |
| FI824483A FI74995C (fi) | 1981-12-28 | 1982-12-28 | Foerfarande foer mikrobiologisk framstaellning av fermenteringsmedia, som innehaoller antingen nebramycin-5' eller en blandning av nebramycin-2, nebramycin-4 och nebramycin-5'. |
| GB08236905A GB2114978B (en) | 1981-12-28 | 1982-12-30 | Microbiological process for preparing nebramycin-2 nebramycin-5 and nebramycin-4 |
| AT400384A AT380489B (de) | 1981-12-28 | 1984-12-17 | Verfahren zur mikrobiologischen herstellung eines gemisches von nebramycin-2, nebramycin-5' und nebramycin-4 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU813954A HU190680B (en) | 1981-12-28 | 1981-12-28 | Process for preparing 6''-0-carbamoyl-tobramycin microbiologically |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HU190680B true HU190680B (en) | 1986-10-28 |
Family
ID=10966213
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU813954A HU190680B (en) | 1981-12-28 | 1981-12-28 | Process for preparing 6''-0-carbamoyl-tobramycin microbiologically |
Country Status (9)
| Country | Link |
|---|---|
| AT (1) | AT379171B (en, 2012) |
| BE (1) | BE895455A (en, 2012) |
| CH (2) | CH658072A5 (en, 2012) |
| DE (1) | DE3248420A1 (en, 2012) |
| FI (1) | FI74995C (en, 2012) |
| FR (1) | FR2519023B1 (en, 2012) |
| GB (1) | GB2114978B (en, 2012) |
| HU (1) | HU190680B (en, 2012) |
| NL (1) | NL8205011A (en, 2012) |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3691279A (en) * | 1970-04-15 | 1972-09-12 | Lilly Co Eli | Antibiotic nebramycin and preparation thereof |
| US3853709A (en) * | 1970-10-26 | 1974-12-10 | Lilly Co Eli | Process for preparing nebramycin factors ii and vii |
| US4032404A (en) * | 1976-07-14 | 1977-06-28 | Bristol-Myers Company | Fermentation process for producing apramycin and nebramycin factor V' |
-
1981
- 1981-12-28 HU HU813954A patent/HU190680B/hu not_active IP Right Cessation
-
1982
- 1982-12-23 BE BE1/10669A patent/BE895455A/fr not_active IP Right Cessation
- 1982-12-27 FR FR8221803A patent/FR2519023B1/fr not_active Expired
- 1982-12-27 CH CH3108/85A patent/CH658072A5/de not_active IP Right Cessation
- 1982-12-27 CH CH7558/82A patent/CH657374A5/de not_active IP Right Cessation
- 1982-12-28 FI FI824483A patent/FI74995C/fi not_active IP Right Cessation
- 1982-12-28 NL NL8205011A patent/NL8205011A/nl not_active Application Discontinuation
- 1982-12-28 AT AT0470482A patent/AT379171B/de not_active IP Right Cessation
- 1982-12-28 DE DE19823248420 patent/DE3248420A1/de active Granted
- 1982-12-30 GB GB08236905A patent/GB2114978B/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE3248420C2 (en, 2012) | 1990-11-08 |
| GB2114978A (en) | 1983-09-01 |
| AT379171B (de) | 1985-11-25 |
| DE3248420A1 (de) | 1983-07-21 |
| FI824483L (fi) | 1983-06-29 |
| ATA470482A (de) | 1985-04-15 |
| FR2519023A1 (fr) | 1983-07-01 |
| FI74995C (fi) | 1988-04-11 |
| FI824483A0 (fi) | 1982-12-28 |
| CH658072A5 (de) | 1986-10-15 |
| NL8205011A (nl) | 1983-07-18 |
| GB2114978B (en) | 1985-09-11 |
| BE895455A (fr) | 1983-06-23 |
| CH657374A5 (de) | 1986-08-29 |
| FR2519023B1 (fr) | 1985-10-25 |
| FI74995B (fi) | 1987-12-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HU90 | Patent valid on 900628 | ||
| HMM4 | Cancellation of final prot. due to non-payment of fee |