BE563122A

BE563122A -

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Publication number: BE563122A
Authority: BE; Belgium
Prior art keywords: distamycin; sep; maxima; methanol; absorption
Prior art date

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English (en)

French (fr)

Publication of BE563122A publication Critical patent/BE563122A/fr

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UPBAOYRENQEPJO-UHFFFAOYSA-N n-[5-[[5-[(3-amino-3-iminopropyl)carbamoyl]-1-methylpyrrol-3-yl]carbamoyl]-1-methylpyrrol-3-yl]-4-formamido-1-methylpyrrole-2-carboxamide Chemical compound CN1C=C(NC=O)C=C1C(=O)NC1=CN(C)C(C(=O)NC2=CN(C)C(C(=O)NCCC(N)=N)=C2)=C1 UPBAOYRENQEPJO-UHFFFAOYSA-N 0.000 claims description 30
239000000047 product Substances 0.000 claims description 29
108010042747 stallimycin Proteins 0.000 claims description 28
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 27
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 20
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 19
239000003242 anti bacterial agent Substances 0.000 claims description 12
229940088710 antibiotic agent Drugs 0.000 claims description 12
238000000034 method Methods 0.000 claims description 10
239000000203 mixture Substances 0.000 claims description 9
239000002904 solvent Substances 0.000 claims description 9
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
238000010521 absorption reaction Methods 0.000 claims description 7
238000000862 absorption spectrum Methods 0.000 claims description 7
244000005700 microbiome Species 0.000 claims description 7
230000003115 biocidal effect Effects 0.000 claims description 5
MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-UHFFFAOYSA-N 0.000 claims description 5
238000000855 fermentation Methods 0.000 claims description 5
230000004151 fermentation Effects 0.000 claims description 5
230000000855 fungicidal effect Effects 0.000 claims description 5
239000002244 precipitate Substances 0.000 claims description 5
241000894007 species Species 0.000 claims description 5
239000000284 extract Substances 0.000 claims description 4
229910052757 nitrogen Inorganic materials 0.000 claims description 4
238000003756 stirring Methods 0.000 claims description 4
241000187747 Streptomyces Species 0.000 claims description 3
241000542929 Streptomyces netropsis Species 0.000 claims description 3
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 3
230000000844 anti-bacterial effect Effects 0.000 claims description 3
238000001914 filtration Methods 0.000 claims description 3
238000001556 precipitation Methods 0.000 claims description 3
150000003839 salts Chemical class 0.000 claims description 3
238000001228 spectrum Methods 0.000 claims description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
108010069713 Distamycins Proteins 0.000 claims description 2
229910052799 carbon Inorganic materials 0.000 claims description 2
125000000623 heterocyclic group Chemical group 0.000 claims description 2
230000008018 melting Effects 0.000 claims description 2
238000002844 melting Methods 0.000 claims description 2
238000002360 preparation method Methods 0.000 claims description 2
229950009902 stallimycin Drugs 0.000 claims description 2
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims 1
150000001338 aliphatic hydrocarbons Chemical class 0.000 claims 1
238000001035 drying Methods 0.000 claims 1
230000001747 exhibiting effect Effects 0.000 claims 1
229910052500 inorganic mineral Inorganic materials 0.000 claims 1
239000011707 mineral Substances 0.000 claims 1
230000000050 nutritive effect Effects 0.000 claims 1
150000004291 polyenes Chemical class 0.000 claims 1
230000001376 precipitating effect Effects 0.000 claims 1
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 14
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
239000001963 growth medium Substances 0.000 description 6
239000000126 substance Substances 0.000 description 6
230000002401 inhibitory effect Effects 0.000 description 5
239000000243 solution Substances 0.000 description 5
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
229920002472 Starch Polymers 0.000 description 4
230000000694 effects Effects 0.000 description 4
238000000605 extraction Methods 0.000 description 4
239000008107 starch Substances 0.000 description 4
238000002211 ultraviolet spectrum Methods 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
240000008042 Zea mays Species 0.000 description 3
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 3
235000002017 Zea mays subsp mays Nutrition 0.000 description 3
150000001298 alcohols Chemical class 0.000 description 3
150000001720 carbohydrates Chemical class 0.000 description 3
235000014633 carbohydrates Nutrition 0.000 description 3
150000001875 compounds Chemical class 0.000 description 3
235000005822 corn Nutrition 0.000 description 3
238000002803 maceration Methods 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
235000014469 Bacillus subtilis Nutrition 0.000 description 2
241000894006 Bacteria Species 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
241000233866 Fungi Species 0.000 description 2
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 2
-1 K2HOP4 Chemical compound 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
101100400378 Mus musculus Marveld2 gene Proteins 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
244000127759 Spondias lutea Species 0.000 description 2
239000002253 acid Substances 0.000 description 2
238000005273 aeration Methods 0.000 description 2
125000001931 aliphatic group Chemical group 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
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 2
239000000706 filtrate Substances 0.000 description 2
238000005194 fractionation Methods 0.000 description 2
239000008273 gelatin Substances 0.000 description 2
229920000159 gelatin Polymers 0.000 description 2
239000008103 glucose Substances 0.000 description 2
229910052602 gypsum Inorganic materials 0.000 description 2
239000010440 gypsum Substances 0.000 description 2
235000012907 honey Nutrition 0.000 description 2
235000013372 meat Nutrition 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
235000019698 starch Nutrition 0.000 description 2
OWEGMIWEEQEYGQ-UHFFFAOYSA-N 100676-05-9 Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC2C(OC(O)C(O)C2O)CO)O1 OWEGMIWEEQEYGQ-UHFFFAOYSA-N 0.000 description 1
ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
NZTWPACKXIQEFV-UHFFFAOYSA-N 2-phenylacetic acid;hydrate Chemical compound O.OC(=O)CC1=CC=CC=C1 NZTWPACKXIQEFV-UHFFFAOYSA-N 0.000 description 1
241000186046 Actinomyces Species 0.000 description 1
102000007469 Actins Human genes 0.000 description 1
108010085238 Actins Proteins 0.000 description 1
229920001817 Agar Polymers 0.000 description 1
241000288976 Arcina Species 0.000 description 1
241000222122 Candida albicans Species 0.000 description 1
240000009226 Corylus americana Species 0.000 description 1
235000001543 Corylus americana Nutrition 0.000 description 1
235000007466 Corylus avellana Nutrition 0.000 description 1
241000196324 Embryophyta Species 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
241000206672 Gelidium Species 0.000 description 1
244000068988 Glycine max Species 0.000 description 1
235000010469 Glycine max Nutrition 0.000 description 1
GUBGYTABKSRVRQ-PICCSMPSSA-N Maltose Natural products O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-PICCSMPSSA-N 0.000 description 1
241000187479 Mycobacterium tuberculosis Species 0.000 description 1
241000589517 Pseudomonas aeruginosa Species 0.000 description 1
240000004808 Saccharomyces cerevisiae Species 0.000 description 1
240000002114 Satureja hortensis Species 0.000 description 1
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
229930006000 Sucrose Natural products 0.000 description 1
MHLMRBVCMNDOCW-UHFFFAOYSA-N acetic acid;butan-1-ol;hydrate Chemical compound O.CC(O)=O.CCCCO MHLMRBVCMNDOCW-UHFFFAOYSA-N 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
235000010419 agar Nutrition 0.000 description 1
238000013019 agitation Methods 0.000 description 1
235000019270 ammonium chloride Nutrition 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
229960001230 asparagine Drugs 0.000 description 1
GUBGYTABKSRVRQ-QUYVBRFLSA-N beta-maltose Chemical compound OC[C@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@@H]1O GUBGYTABKSRVRQ-QUYVBRFLSA-N 0.000 description 1
238000012474 bioautography Methods 0.000 description 1
239000001058 brown pigment Substances 0.000 description 1
YHSWOTTUSPRHEZ-UHFFFAOYSA-N butan-1-ol;pyridine;hydrate Chemical compound O.CCCCO.C1=CC=NC=C1 YHSWOTTUSPRHEZ-UHFFFAOYSA-N 0.000 description 1
235000010216 calcium carbonate Nutrition 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
229940095731 candida albicans Drugs 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
229920000547 conjugated polymer Polymers 0.000 description 1
239000000470 constituent Substances 0.000 description 1
239000012043 crude product Substances 0.000 description 1
238000012258 culturing Methods 0.000 description 1
238000001514 detection method Methods 0.000 description 1
239000008121 dextrose Substances 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
238000010828 elution Methods 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
235000013312 flour Nutrition 0.000 description 1
244000053095 fungal pathogen Species 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
239000002609 medium Substances 0.000 description 1
230000004060 metabolic process Effects 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
230000001717 pathogenic effect Effects 0.000 description 1
YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 1
230000019612 pigmentation Effects 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000002689 soil Substances 0.000 description 1
239000000758 substrate Substances 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
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238000005406 washing Methods 0.000 description 1