BE569746A - - Google Patents

Info

Publication number

BE569746A

BE569746A BE569746DA BE569746A BE 569746 A BE569746 A BE 569746A BE 569746D A BE569746D A BE 569746DA BE 569746 A BE569746 A BE 569746A

Authority

BE

Belgium

Prior art keywords

antibiotic

sep

water

acid

components

Prior art date

Links

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• 230000003115 biocidal effect Effects 0.000 claims description 83
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 56
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 54
• 239000000243 solution Substances 0.000 claims description 51
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 50
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 47
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 37
• 239000000203 mixture Substances 0.000 claims description 37
• YRMCBQLZVBXOSJ-PCFSSPOYSA-N (e)-3-[(6r,6as)-4-hydroxy-6-methoxy-3-methyl-11-oxo-5,6,6a,7-tetrahydropyrrolo[2,1-c][1,4]benzodiazepin-8-yl]prop-2-enamide Chemical compound CO[C@H]1NC2=C(O)C(C)=CC=C2C(=O)N2C=C(\C=C\C(N)=O)C[C@@H]12 YRMCBQLZVBXOSJ-PCFSSPOYSA-N 0.000 claims description 29
• 150000003839 salts Chemical class 0.000 claims description 25
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 23
• 238000000034 method Methods 0.000 claims description 16
• 239000002585 base Substances 0.000 claims description 14
• 239000002253 acid Substances 0.000 claims description 12
• 238000004587 chromatography analysis Methods 0.000 claims description 10
• 239000007864 aqueous solution Substances 0.000 claims description 8
• 239000002244 precipitate Substances 0.000 claims description 8
• 239000003960 organic solvent Substances 0.000 claims description 7
• 239000002904 solvent Substances 0.000 claims description 6
• 239000012736 aqueous medium Substances 0.000 claims description 5
• 239000001913 cellulose Substances 0.000 claims description 5
• 229920002678 cellulose Polymers 0.000 claims description 5
• 239000003795 chemical substances by application Substances 0.000 claims description 5
• 239000012458 free base Substances 0.000 claims description 4
• 150000002500 ions Chemical class 0.000 claims description 4
• 239000000825 pharmaceutical preparation Substances 0.000 claims description 4
• OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 claims description 4
• 239000000047 product Substances 0.000 claims description 4
• QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 3
• 150000001768 cations Chemical class 0.000 claims description 3
• 150000007524 organic acids Chemical class 0.000 claims description 3
• 229910021653 sulphate ion Inorganic materials 0.000 claims description 3
• 230000002378 acidificating effect Effects 0.000 claims description 2
• 150000001450 anions Chemical class 0.000 claims description 2
• RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 claims description 2
• 229910001863 barium hydroxide Inorganic materials 0.000 claims description 2
• 235000019161 pantothenic acid Nutrition 0.000 claims description 2
• 238000000638 solvent extraction Methods 0.000 claims description 2
• GHOKWGTUZJEAQD-ZETCQYMHSA-N (D)-(+)-Pantothenic acid Chemical compound OCC(C)(C)[C@@H](O)C(=O)NCCC(O)=O GHOKWGTUZJEAQD-ZETCQYMHSA-N 0.000 claims 1
• 229910019142 PO4 Inorganic materials 0.000 claims 1
• 239000003957 anion exchange resin Substances 0.000 claims 1
• 150000007529 inorganic bases Chemical class 0.000 claims 1
• 229910017053 inorganic salt Inorganic materials 0.000 claims 1
• 238000002955 isolation Methods 0.000 claims 1
• 150000007522 mineralic acids Chemical class 0.000 claims 1
• 229940014662 pantothenate Drugs 0.000 claims 1
• 239000011713 pantothenic acid Substances 0.000 claims 1
• 235000021317 phosphate Nutrition 0.000 claims 1
• 150000003013 phosphoric acid derivatives Chemical class 0.000 claims 1
• 150000003467 sulfuric acid derivatives Chemical class 0.000 claims 1
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 38
• LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 30
• 239000000706 filtrate Substances 0.000 description 27
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 20
• 239000000126 substance Substances 0.000 description 17
• 239000008346 aqueous phase Substances 0.000 description 16
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
• 238000002360 preparation method Methods 0.000 description 14
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
• 235000015097 nutrients Nutrition 0.000 description 12
• 239000000284 extract Substances 0.000 description 11
• 239000012071 phase Substances 0.000 description 11
• DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 10
• 238000001914 filtration Methods 0.000 description 10
• 239000012074 organic phase Substances 0.000 description 10
• 239000000843 powder Substances 0.000 description 10
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 9
• 229960000583 acetic acid Drugs 0.000 description 9
• 229920005989 resin Polymers 0.000 description 9
• 239000011347 resin Substances 0.000 description 9
• 241000187747 Streptomyces Species 0.000 description 8
• 239000003242 anti bacterial agent Substances 0.000 description 8
• 238000010828 elution Methods 0.000 description 8
• 239000011734 sodium Substances 0.000 description 8
• 229910052708 sodium Inorganic materials 0.000 description 8
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
• 239000007853 buffer solution Substances 0.000 description 7
• 230000000694 effects Effects 0.000 description 7
• 239000012362 glacial acetic acid Substances 0.000 description 7
• 239000003208 petroleum Substances 0.000 description 7
• 238000003756 stirring Methods 0.000 description 7
• USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 6
• 239000005695 Ammonium acetate Substances 0.000 description 6
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
• 229940043376 ammonium acetate Drugs 0.000 description 6
• 235000019257 ammonium acetate Nutrition 0.000 description 6
• 238000006243 chemical reaction Methods 0.000 description 6
• 239000012141 concentrate Substances 0.000 description 6
• 229920001817 Agar Polymers 0.000 description 5
• DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 5
• 235000010469 Glycine max Nutrition 0.000 description 5
• 229920002472 Starch Polymers 0.000 description 5
• 239000008272 agar Substances 0.000 description 5
• 150000001875 compounds Chemical class 0.000 description 5
• 235000013312 flour Nutrition 0.000 description 5
• 239000008103 glucose Substances 0.000 description 5
• 239000007788 liquid Substances 0.000 description 5
• 239000000463 material Substances 0.000 description 5
• 239000008107 starch Substances 0.000 description 5
• 235000019698 starch Nutrition 0.000 description 5
• 238000005406 washing Methods 0.000 description 5
• DPEYHNFHDIXMNV-UHFFFAOYSA-N (9-amino-3-bicyclo[3.3.1]nonanyl)-(4-benzyl-5-methyl-1,4-diazepan-1-yl)methanone dihydrochloride Chemical compound Cl.Cl.CC1CCN(CCN1Cc1ccccc1)C(=O)C1CC2CCCC(C1)C2N DPEYHNFHDIXMNV-UHFFFAOYSA-N 0.000 description 4
• XPCTZQVDEJYUGT-UHFFFAOYSA-N 3-hydroxy-2-methyl-4-pyrone Chemical compound CC=1OC=CC(=O)C=1O XPCTZQVDEJYUGT-UHFFFAOYSA-N 0.000 description 4
• 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 4
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
• 229910002651 NO3 Inorganic materials 0.000 description 4
• NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 4
• 150000007513 acids Chemical class 0.000 description 4
• 238000001035 drying Methods 0.000 description 4
• 238000005057 refrigeration Methods 0.000 description 4
• UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 4
• -1 D-mannite Chemical compound 0.000 description 3
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
• GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 3
• 241000699670 Mus sp. Species 0.000 description 3
• 241000191967 Staphylococcus aureus Species 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
• 239000002156 adsorbate Substances 0.000 description 3
• 239000003463 adsorbent Substances 0.000 description 3
• 229940088710 antibiotic agent Drugs 0.000 description 3
• TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 3
• 150000001720 carbohydrates Chemical class 0.000 description 3
• 235000014633 carbohydrates Nutrition 0.000 description 3
• 229920001429 chelating resin Polymers 0.000 description 3
• 235000005822 corn Nutrition 0.000 description 3
• 239000008101 lactose Substances 0.000 description 3
• 239000002609 medium Substances 0.000 description 3
• 230000035772 mutation Effects 0.000 description 3
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
• 229920006395 saturated elastomer Polymers 0.000 description 3
• 238000001179 sorption measurement Methods 0.000 description 3
• 239000007858 starting material Substances 0.000 description 3
• QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical class S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
• 241000186361 Actinobacteria <class> Species 0.000 description 2
• 241000894006 Bacteria Species 0.000 description 2
• OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
• BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
• FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 2
• 241000588724 Escherichia coli Species 0.000 description 2
• 108010010803 Gelatin Proteins 0.000 description 2
• 244000068988 Glycine max Species 0.000 description 2
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
• 229910021578 Iron(III) chloride Inorganic materials 0.000 description 2
• HYMLWHLQFGRFIY-UHFFFAOYSA-N Maltol Natural products CC1OC=CC(=O)C1=O HYMLWHLQFGRFIY-UHFFFAOYSA-N 0.000 description 2
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
• 241001494960 Streptomyces griseoflavus Species 0.000 description 2
• 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 2
• 229930006000 Sucrose Natural products 0.000 description 2
• 238000013019 agitation Methods 0.000 description 2
• 150000001298 alcohols Chemical class 0.000 description 2
• 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
• 230000000844 anti-bacterial effect Effects 0.000 description 2
• 239000006286 aqueous extract Substances 0.000 description 2
• 239000000872 buffer Substances 0.000 description 2
• 239000011575 calcium Substances 0.000 description 2
• 229910052791 calcium Inorganic materials 0.000 description 2
• OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
• 229910052799 carbon Inorganic materials 0.000 description 2
• 235000013339 cereals Nutrition 0.000 description 2
• HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
• 230000007423 decrease Effects 0.000 description 2
• 230000001747 exhibiting effect Effects 0.000 description 2
• 239000008273 gelatin Substances 0.000 description 2
• 229920000159 gelatin Polymers 0.000 description 2
• 235000019322 gelatine Nutrition 0.000 description 2
• 235000011852 gelatine desserts Nutrition 0.000 description 2
• 235000011187 glycerol Nutrition 0.000 description 2
• 230000007062 hydrolysis Effects 0.000 description 2
• 238000006460 hydrolysis reaction Methods 0.000 description 2
• 239000012535 impurity Substances 0.000 description 2
• RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 2
• HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
• 229940043353 maltol Drugs 0.000 description 2
• 235000010355 mannitol Nutrition 0.000 description 2
• 230000007935 neutral effect Effects 0.000 description 2
• FEMOMIGRRWSMCU-UHFFFAOYSA-N ninhydrin Chemical compound C1=CC=C2C(=O)C(O)(O)C(=O)C2=C1 FEMOMIGRRWSMCU-UHFFFAOYSA-N 0.000 description 2
• 229910017464 nitrogen compound Inorganic materials 0.000 description 2
• 150000002830 nitrogen compounds Chemical class 0.000 description 2
• 238000004810 partition chromatography Methods 0.000 description 2
• 229920001467 poly(styrenesulfonates) Polymers 0.000 description 2
• 230000001737 promoting effect Effects 0.000 description 2
• 108010062729 ristocetin A Proteins 0.000 description 2
• 239000007787 solid Substances 0.000 description 2
• 229960005322 streptomycin Drugs 0.000 description 2
• 238000007920 subcutaneous administration Methods 0.000 description 2
• 229960004793 sucrose Drugs 0.000 description 2
• 238000002211 ultraviolet spectrum Methods 0.000 description 2
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
• HVYWMOMLDIMFJA-UHFFFAOYSA-N 3-cholesterol Natural products C1C=C2CC(O)CCC2(C)C2C1C1CCC(C(C)CCCC(C)C)C1(C)CC2 HVYWMOMLDIMFJA-UHFFFAOYSA-N 0.000 description 1
• VUOPFFVAZTUEGW-SRXUPNLNSA-N 32p08cbb99 Chemical compound C=1C([C@@H]2C(=O)N[C@@H]([C@@H](C3=CC=C(C=C3)OC=3C=C4C=C(C=3O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@@H](CO[C@H]5[C@@H]([C@H](O)[C@@H](O)[C@H](C)O5)O)O3)O[C@@H]3[C@H]([C@@H](O)[C@H](O)[C@@H](CO)O3)O[C@H]3[C@H]([C@H](O)[C@H](O)CO3)O)OC3=CC=C(C=C3)[C@@H](O)[C@@H]3C(=O)N[C@@H](C=5C=C(C(=C(O)C=5)C)OC=5C(O)=CC=C(C=5)[C@@H](N)C(=O)N3)C(=O)N[C@H]4C(=O)N2)O[C@@H]2O[C@@H](C)[C@H](O)[C@H](N)C2)C(=O)N[C@@H](C2=CC(O)=C3)C(=O)OC)=CC=C(O)C=1C2=C3O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]1O VUOPFFVAZTUEGW-SRXUPNLNSA-N 0.000 description 1
• YECWLNHQVUKZLG-LHYOAFRFSA-N 377sgf21w3 Chemical compound O([C@@H]1C2=CC=C(C=C2)OC=2C=C3C=C(C=2O[C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO[C@H]4[C@@H]([C@H](O)[C@@H](O)[C@H](C)O4)O)O2)O)OC2=CC=C(C=C2)[C@@H](O)[C@@H]2C(=O)N[C@@H](C=4C=C(C(=C(O)C=4)C)OC=4C(O)=CC=C(C=4)[C@@H](N)C(=O)N2)C(=O)N[C@H]3C(=O)N[C@H]2C(=O)N[C@@H]1C(=O)N[C@@H](C1=CC(O)=CC(O[C@H]3[C@H]([C@@H](O)[C@H](O)[C@@H](CO)O3)O)=C1C=1C(O)=CC=C2C=1)C(=O)OC)[C@H]1C[C@@H](N)[C@@H](O)[C@H](C)O1 YECWLNHQVUKZLG-LHYOAFRFSA-N 0.000 description 1
• GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
• NNDHDYDFEDRMGH-CAEIVAEBSA-N Anthranoyllycoctonine Chemical compound C([C@]12CN(C3[C@@]4(O)[C@]5(O)[C@H]6[C@@H](OC)[C@@H]([C@H](C5)OC)C[C@H]6[C@@]3([C@@H]1[C@@H]4OC)[C@@H](OC)CC2)CC)OC(=O)C1=CC=CC=C1N NNDHDYDFEDRMGH-CAEIVAEBSA-N 0.000 description 1
• DCXYFEDJOCDNAF-UHFFFAOYSA-N Asparagine Natural products OC(=O)C(N)CC(N)=O DCXYFEDJOCDNAF-UHFFFAOYSA-N 0.000 description 1
• 241000193830 Bacillus <bacterium> Species 0.000 description 1
• 241000194107 Bacillus megaterium Species 0.000 description 1
• 244000063299 Bacillus subtilis Species 0.000 description 1
• 235000014469 Bacillus subtilis Nutrition 0.000 description 1
• 241000186216 Corynebacterium Species 0.000 description 1
• 229920000742 Cotton Polymers 0.000 description 1
• DYDCUQKUCUHJBH-UWTATZPHSA-N D-Cycloserine Chemical compound N[C@@H]1CONC1=O DYDCUQKUCUHJBH-UWTATZPHSA-N 0.000 description 1
• DYDCUQKUCUHJBH-UHFFFAOYSA-N D-Cycloserine Natural products NC1CONC1=O DYDCUQKUCUHJBH-UHFFFAOYSA-N 0.000 description 1
• RFSUNEUAIZKAJO-VRPWFDPXSA-N D-Fructose Natural products OC[C@H]1OC(O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-VRPWFDPXSA-N 0.000 description 1
• FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
• SHZGCJCMOBCMKK-UHFFFAOYSA-N D-mannomethylose Natural products CC1OC(O)C(O)C(O)C1O SHZGCJCMOBCMKK-UHFFFAOYSA-N 0.000 description 1
• 108010092160 Dactinomycin Proteins 0.000 description 1
• 244000000626 Daucus carota Species 0.000 description 1
• 235000002767 Daucus carota Nutrition 0.000 description 1
• 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
• 241000233866 Fungi Species 0.000 description 1
• UXOXDDUEWZOAIW-UHFFFAOYSA-N Inuline Natural products CCN1CC2(CC(=O)Oc3ccccc3N)CCC(OC)C45C6CC7C(CC(O)(C6C7OC)C(O)(C(OC)C24)C15)OC UXOXDDUEWZOAIW-UHFFFAOYSA-N 0.000 description 1
• DCXYFEDJOCDNAF-REOHCLBHSA-N L-asparagine Chemical compound OC(=O)[C@@H](N)CC(N)=O DCXYFEDJOCDNAF-REOHCLBHSA-N 0.000 description 1
• PNNNRSAQSRJVSB-UHFFFAOYSA-N L-rhamnose Natural products CC(O)C(O)C(O)C(O)C=O PNNNRSAQSRJVSB-UHFFFAOYSA-N 0.000 description 1
• FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
• PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
• 239000001888 Peptone Substances 0.000 description 1
• 108010080698 Peptones Proteins 0.000 description 1
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