NO319146B1 - Mikrobiologisk fremgangsmate for fremstilling av heteroaromatiske karboksylsyrer og picolinsyre eller deres fysiologisk fordragelige salter ved hjelp av mikroorganismer fra slekten Alcaligenes - Google Patents
Mikrobiologisk fremgangsmate for fremstilling av heteroaromatiske karboksylsyrer og picolinsyre eller deres fysiologisk fordragelige salter ved hjelp av mikroorganismer fra slekten Alcaligenes Download PDFInfo
- Publication number
- NO319146B1 NO319146B1 NO19962389A NO962389A NO319146B1 NO 319146 B1 NO319146 B1 NO 319146B1 NO 19962389 A NO19962389 A NO 19962389A NO 962389 A NO962389 A NO 962389A NO 319146 B1 NO319146 B1 NO 319146B1
- Authority
- NO
- Norway
- Prior art keywords
- acid
- microorganisms
- biotransformation
- physiologically tolerable
- cyanopyridine
- Prior art date
Links
- 244000005700 microbiome Species 0.000 title claims abstract description 21
- -1 heteroaromatic carboxylic acids Chemical class 0.000 title claims abstract description 18
- 150000003839 salts Chemical class 0.000 title claims abstract description 18
- 241000588986 Alcaligenes Species 0.000 title claims abstract description 8
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical compound OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 title claims description 40
- 229940081066 picolinic acid Drugs 0.000 title claims description 20
- 238000000034 method Methods 0.000 title claims description 11
- 230000002906 microbiologic effect Effects 0.000 title claims 3
- 238000002360 preparation method Methods 0.000 title description 5
- 150000001720 carbohydrates Chemical class 0.000 claims abstract description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 7
- 230000036983 biotransformation Effects 0.000 claims description 23
- 239000000758 substrate Substances 0.000 claims description 13
- 238000004519 manufacturing process Methods 0.000 claims description 11
- 241000588813 Alcaligenes faecalis Species 0.000 claims description 8
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 7
- 238000013048 microbiological method Methods 0.000 claims description 6
- 150000001735 carboxylic acids Chemical class 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 2
- QWIZKRHEGXHVAS-UHFFFAOYSA-N 2-methyl-1H-pyridine-2-carbonitrile Chemical compound N#CC1(C)NC=CC=C1 QWIZKRHEGXHVAS-UHFFFAOYSA-N 0.000 claims 1
- 150000003627 tricarboxylic acid derivatives Chemical class 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 abstract description 8
- 150000003628 tricarboxylic acids Chemical class 0.000 abstract description 6
- FFNVQNRYTPFDDP-UHFFFAOYSA-N 2-cyanopyridine Chemical compound N#CC1=CC=CC=N1 FFNVQNRYTPFDDP-UHFFFAOYSA-N 0.000 description 20
- VRCWSYYXUCKEED-UHFFFAOYSA-N 6-Hydroxypicolinic acid Chemical compound OC(=O)C1=CC=CC(=O)N1 VRCWSYYXUCKEED-UHFFFAOYSA-N 0.000 description 15
- 239000000243 solution Substances 0.000 description 12
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 9
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 8
- 239000002609 medium Substances 0.000 description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
- PMSVVUSIPKHUMT-UHFFFAOYSA-N cyanopyrazine Chemical compound N#CC1=CN=CC=N1 PMSVVUSIPKHUMT-UHFFFAOYSA-N 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 229940005347 alcaligenes faecalis Drugs 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 235000014633 carbohydrates Nutrition 0.000 description 5
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 5
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 4
- 239000001744 Sodium fumarate Substances 0.000 description 4
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 4
- MSJMDZAOKORVFC-SEPHDYHBSA-L disodium fumarate Chemical compound [Na+].[Na+].[O-]C(=O)\C=C\C([O-])=O MSJMDZAOKORVFC-SEPHDYHBSA-L 0.000 description 4
- 229940005573 sodium fumarate Drugs 0.000 description 4
- 235000019294 sodium fumarate Nutrition 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- PGZHSVWXFKKCNR-UHFFFAOYSA-N 6-chloropyridine-2-carbonitrile Chemical compound ClC1=CC=CC(C#N)=N1 PGZHSVWXFKKCNR-UHFFFAOYSA-N 0.000 description 3
- LHXIGTYJDLGWRO-UHFFFAOYSA-N 6-oxo-1h-pyrazine-2-carboxylic acid Chemical compound OC(=O)C1=CN=CC(O)=N1 LHXIGTYJDLGWRO-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 238000002835 absorbance Methods 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 239000006285 cell suspension Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000001530 fumaric acid Substances 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- NIPZZXUFJPQHNH-UHFFFAOYSA-N pyrazine-2-carboxylic acid Chemical compound OC(=O)C1=CN=CC=N1 NIPZZXUFJPQHNH-UHFFFAOYSA-N 0.000 description 3
- 239000002028 Biomass Substances 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 2
- 235000011132 calcium sulphate Nutrition 0.000 description 2
- 229910052804 chromium Inorganic materials 0.000 description 2
- 239000011651 chromium Substances 0.000 description 2
- 150000001991 dicarboxylic acids Chemical class 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 229940050411 fumarate Drugs 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 235000001968 nicotinic acid Nutrition 0.000 description 2
- 229960003512 nicotinic acid Drugs 0.000 description 2
- 239000011664 nicotinic acid Substances 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 230000000284 resting effect Effects 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 2
- ODBLHEXUDAPZAU-UHFFFAOYSA-N threo-D-isocitric acid Natural products OC(=O)C(O)C(C(O)=O)CC(O)=O ODBLHEXUDAPZAU-UHFFFAOYSA-N 0.000 description 2
- HDTRYLNUVZCQOY-UHFFFAOYSA-N α-D-glucopyranosyl-α-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OC1C(O)C(O)C(O)C(CO)O1 HDTRYLNUVZCQOY-UHFFFAOYSA-N 0.000 description 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- VXXVUHAXJHEYFH-SEPHDYHBSA-N (e)-but-2-enedioic acid;sodium Chemical compound [Na].[Na].OC(=O)\C=C\C(O)=O VXXVUHAXJHEYFH-SEPHDYHBSA-N 0.000 description 1
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- 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
- KPGXRSRHYNQIFN-UHFFFAOYSA-N 2-oxoglutaric acid Chemical compound OC(=O)CCC(=O)C(O)=O KPGXRSRHYNQIFN-UHFFFAOYSA-N 0.000 description 1
- PDRSZXQBFCYYKZ-UHFFFAOYSA-N 5,6-dichloropyridine-2-carbonitrile Chemical compound ClC1=CC=C(C#N)N=C1Cl PDRSZXQBFCYYKZ-UHFFFAOYSA-N 0.000 description 1
- JJBZLBWDCGBCON-UHFFFAOYSA-N 5-bromo-6-chloropyrazine-2-carbonitrile Chemical compound ClC1=NC(C#N)=CN=C1Br JJBZLBWDCGBCON-UHFFFAOYSA-N 0.000 description 1
- CZPOFSDHJNNWQL-UHFFFAOYSA-N 6-chloropyrazine-2-carbonitrile Chemical compound ClC1=CN=CC(C#N)=N1 CZPOFSDHJNNWQL-UHFFFAOYSA-N 0.000 description 1
- ZLKMOIHCHCMSFW-UHFFFAOYSA-N 6-chloropyridine-2-carboxylic acid Chemical compound OC(=O)C1=CC=CC(Cl)=N1 ZLKMOIHCHCMSFW-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 102000004092 Amidohydrolases Human genes 0.000 description 1
- 108090000531 Amidohydrolases Proteins 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 241000193830 Bacillus <bacterium> Species 0.000 description 1
- 241000186146 Brevibacterium Species 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- 241001631457 Cannula Species 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-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
- 241000186216 Corynebacterium Species 0.000 description 1
- ODBLHEXUDAPZAU-ZAFYKAAXSA-N D-threo-isocitric acid Chemical compound OC(=O)[C@H](O)[C@@H](C(O)=O)CC(O)=O ODBLHEXUDAPZAU-ZAFYKAAXSA-N 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 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 1
- ODBLHEXUDAPZAU-FONMRSAGSA-N Isocitric acid Natural products OC(=O)[C@@H](O)[C@H](C(O)=O)CC(O)=O ODBLHEXUDAPZAU-FONMRSAGSA-N 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
- 241000192041 Micrococcus Species 0.000 description 1
- 108010033272 Nitrilase Proteins 0.000 description 1
- 108010024026 Nitrile hydratase Proteins 0.000 description 1
- 241000187654 Nocardia Species 0.000 description 1
- MUPFEKGTMRGPLJ-RMMQSMQOSA-N Raffinose Natural products O(C[C@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@@H](O[C@@]2(CO)[C@H](O)[C@@H](O)[C@@H](CO)O2)O1)[C@@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 MUPFEKGTMRGPLJ-RMMQSMQOSA-N 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 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
- HDTRYLNUVZCQOY-WSWWMNSNSA-N Trehalose Natural products O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 HDTRYLNUVZCQOY-WSWWMNSNSA-N 0.000 description 1
- MUPFEKGTMRGPLJ-UHFFFAOYSA-N UNPD196149 Natural products OC1C(O)C(CO)OC1(CO)OC1C(O)C(O)C(O)C(COC2C(C(O)C(O)C(CO)O2)O)O1 MUPFEKGTMRGPLJ-UHFFFAOYSA-N 0.000 description 1
- 229940091179 aconitate Drugs 0.000 description 1
- GTZCVFVGUGFEME-UHFFFAOYSA-N aconitic acid Chemical compound OC(=O)CC(C(O)=O)=CC(O)=O GTZCVFVGUGFEME-UHFFFAOYSA-N 0.000 description 1
- HDTRYLNUVZCQOY-LIZSDCNHSA-N alpha,alpha-trehalose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 HDTRYLNUVZCQOY-LIZSDCNHSA-N 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 230000003698 anagen phase Effects 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- DYVKGOVCCLREIY-UHFFFAOYSA-N azanium;pyridine-2-carboxylate Chemical compound [NH4+].[O-]C(=O)C1=CC=CC=N1 DYVKGOVCCLREIY-UHFFFAOYSA-N 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
- 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
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 235000011148 calcium chloride Nutrition 0.000 description 1
- 239000001175 calcium sulphate Substances 0.000 description 1
- PDEKDNMUYVDZCL-UHFFFAOYSA-N calcium;pyridine-2-carboxylic acid Chemical compound [Ca].OC(=O)C1=CC=CC=N1 PDEKDNMUYVDZCL-UHFFFAOYSA-N 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 150000001844 chromium Chemical class 0.000 description 1
- 229940046374 chromium picolinate Drugs 0.000 description 1
- LJAOOBNHPFKCDR-UHFFFAOYSA-K chromium(3+) trichloride hexahydrate Chemical compound O.O.O.O.O.O.[Cl-].[Cl-].[Cl-].[Cr+3] LJAOOBNHPFKCDR-UHFFFAOYSA-K 0.000 description 1
- GJYSUGXFENSLOO-UHFFFAOYSA-N chromium;pyridine-2-carboxylic acid Chemical compound [Cr].OC(=O)C1=CC=CC=N1.OC(=O)C1=CC=CC=N1.OC(=O)C1=CC=CC=N1 GJYSUGXFENSLOO-UHFFFAOYSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 1
- 150000002016 disaccharides Chemical class 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 230000012010 growth Effects 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 239000000411 inducer Substances 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 150000003951 lactams Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229940049920 malate Drugs 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 150000002772 monosaccharides Chemical class 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- KHPXUQMNIQBQEV-UHFFFAOYSA-N oxaloacetic acid Chemical compound OC(=O)CC(=O)C(O)=O KHPXUQMNIQBQEV-UHFFFAOYSA-N 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- IBBMAWULFFBRKK-UHFFFAOYSA-N picolinamide Chemical compound NC(=O)C1=CC=CC=N1 IBBMAWULFFBRKK-UHFFFAOYSA-N 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- MUPFEKGTMRGPLJ-ZQSKZDJDSA-N raffinose 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[C@@H]2[C@@H]([C@@H](O)[C@@H](O)[C@@H](CO)O2)O)O1 MUPFEKGTMRGPLJ-ZQSKZDJDSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- PRWXGRGLHYDWPS-UHFFFAOYSA-L sodium malonate Chemical compound [Na+].[Na+].[O-]C(=O)CC([O-])=O PRWXGRGLHYDWPS-UHFFFAOYSA-L 0.000 description 1
- ZDQYSKICYIVCPN-UHFFFAOYSA-L sodium succinate (anhydrous) Chemical compound [Na+].[Na+].[O-]C(=O)CCC([O-])=O ZDQYSKICYIVCPN-UHFFFAOYSA-L 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- VNOYUJKHFWYWIR-ITIYDSSPSA-N succinyl-CoA Chemical compound O[C@@H]1[C@H](OP(O)(O)=O)[C@@H](COP(O)(=O)OP(O)(=O)OCC(C)(C)[C@@H](O)C(=O)NCCC(=O)NCCSC(=O)CCC(O)=O)O[C@H]1N1C2=NC=NC(N)=C2N=C1 VNOYUJKHFWYWIR-ITIYDSSPSA-N 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000005846 sugar alcohols Chemical class 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 150000004043 trisaccharides Chemical class 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
- 238000009423 ventilation Methods 0.000 description 1
- 238000010626 work up procedure Methods 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
- C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
- C12P17/10—Nitrogen as only ring hetero atom
- C12P17/12—Nitrogen as only ring hetero atom containing a six-membered hetero ring
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Microbiology (AREA)
- General Chemical & Material Sciences (AREA)
- Biotechnology (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Pyridine Compounds (AREA)
- Micro-Organisms Or Cultivation Processes Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH166495 | 1995-06-07 | ||
| CH173395 | 1995-06-13 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO962389D0 NO962389D0 (no) | 1996-06-06 |
| NO962389L NO962389L (no) | 1996-12-09 |
| NO319146B1 true NO319146B1 (no) | 2005-06-27 |
Family
ID=25688320
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO19962389A NO319146B1 (no) | 1995-06-07 | 1996-06-06 | Mikrobiologisk fremgangsmate for fremstilling av heteroaromatiske karboksylsyrer og picolinsyre eller deres fysiologisk fordragelige salter ved hjelp av mikroorganismer fra slekten Alcaligenes |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US5702930A (zh) |
| EP (1) | EP0747486B1 (zh) |
| JP (1) | JP3810860B2 (zh) |
| KR (1) | KR100471703B1 (zh) |
| CN (1) | CN1127573C (zh) |
| AT (1) | ATE186328T1 (zh) |
| CA (1) | CA2177651C (zh) |
| CZ (1) | CZ288989B6 (zh) |
| DE (1) | DE59603534D1 (zh) |
| DK (1) | DK0747486T3 (zh) |
| ES (1) | ES2140757T3 (zh) |
| HU (1) | HU219855B (zh) |
| NO (1) | NO319146B1 (zh) |
| PT (1) | PT747486E (zh) |
| SK (1) | SK281873B6 (zh) |
| TW (1) | TW528803B (zh) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5492876B2 (ja) * | 2009-04-30 | 2014-05-14 | 三井化学株式会社 | ３−メルカプトプロピオン酸またはその塩を製造する方法 |
| CN109251169B (zh) * | 2018-10-08 | 2022-08-16 | 盐城工学院 | 一种利用2-op精馏残渣制备吡啶-2-甲酸铬的方法 |
| CN111072558B (zh) * | 2019-11-05 | 2022-05-24 | 南京红太阳生物化学有限责任公司 | 一种2,3-二氯-6-氰基吡啶的制备方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61162191A (ja) * | 1985-01-11 | 1986-07-22 | Nitto Chem Ind Co Ltd | 微生物による有機酸類の製造法 |
| JP3009421B2 (ja) * | 1990-02-28 | 2000-02-14 | 秀明 山田 | 有機酸の生物学的製造法 |
| GB9005965D0 (en) * | 1990-03-16 | 1990-05-09 | Shell Int Research | Herbicidal carboxamide derivatives |
| US5264361A (en) * | 1991-03-18 | 1993-11-23 | Lonza Ltd. | Microbiological process for the production of 6-hydroxypicolinic acid |
| US5270203A (en) * | 1992-03-13 | 1993-12-14 | Lonza Ltd. | Biologically pure culture of Alcaligenes faecalis DSM 6335 |
-
1996
- 1996-05-29 CA CA002177651A patent/CA2177651C/en not_active Expired - Fee Related
- 1996-06-04 SK SK716-96A patent/SK281873B6/sk not_active IP Right Cessation
- 1996-06-05 CZ CZ19961636A patent/CZ288989B6/cs not_active IP Right Cessation
- 1996-06-05 ES ES96109088T patent/ES2140757T3/es not_active Expired - Lifetime
- 1996-06-05 AT AT96109088T patent/ATE186328T1/de active
- 1996-06-05 DE DE59603534T patent/DE59603534D1/de not_active Expired - Lifetime
- 1996-06-05 DK DK96109088T patent/DK0747486T3/da active
- 1996-06-05 JP JP14271996A patent/JP3810860B2/ja not_active Expired - Fee Related
- 1996-06-05 PT PT96109088T patent/PT747486E/pt unknown
- 1996-06-05 EP EP96109088A patent/EP0747486B1/de not_active Expired - Lifetime
- 1996-06-06 NO NO19962389A patent/NO319146B1/no not_active IP Right Cessation
- 1996-06-06 US US08/659,362 patent/US5702930A/en not_active Expired - Lifetime
- 1996-06-07 CN CN96110476A patent/CN1127573C/zh not_active Expired - Fee Related
- 1996-06-07 HU HU9601582A patent/HU219855B/hu not_active IP Right Cessation
- 1996-06-07 KR KR1019960020328A patent/KR100471703B1/ko not_active IP Right Cessation
- 1996-06-12 TW TW085107071A patent/TW528803B/zh not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| DE59603534D1 (de) | 1999-12-09 |
| CZ288989B6 (cs) | 2001-10-17 |
| HUP9601582A3 (en) | 2000-04-28 |
| CN1127573C (zh) | 2003-11-12 |
| US5702930A (en) | 1997-12-30 |
| TW528803B (en) | 2003-04-21 |
| CZ163696A3 (en) | 1997-01-15 |
| CN1145956A (zh) | 1997-03-26 |
| JPH08332094A (ja) | 1996-12-17 |
| DK0747486T3 (da) | 2000-01-31 |
| HU9601582D0 (en) | 1996-07-29 |
| HUP9601582A2 (en) | 1997-03-28 |
| KR100471703B1 (ko) | 2005-06-20 |
| SK281873B6 (sk) | 2001-08-06 |
| PT747486E (pt) | 2000-04-28 |
| HU219855B (hu) | 2001-08-28 |
| ES2140757T3 (es) | 2000-03-01 |
| KR970001546A (ko) | 1997-01-24 |
| EP0747486A1 (de) | 1996-12-11 |
| CA2177651C (en) | 2008-01-22 |
| ATE186328T1 (de) | 1999-11-15 |
| NO962389D0 (no) | 1996-06-06 |
| SK71696A3 (en) | 1997-01-08 |
| EP0747486B1 (de) | 1999-11-03 |
| JP3810860B2 (ja) | 2006-08-16 |
| NO962389L (no) | 1996-12-09 |
| CA2177651A1 (en) | 1996-12-08 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Nabe et al. | Conversion of glycerol to dihydroxyacetone by immobilized whole cells of Acetobacter xylinum | |
| US5312741A (en) | Process for producing 2-keto-L-gulonic acid | |
| EP0046284B1 (en) | Method for preparing 2,5-diketo-d-gluconic acid and microorganisms for carrying out the method | |
| NO134546B (zh) | ||
| NO159608B (no) | Fremgangsm te for fremstilling av 6-hydroksynikotin | |
| US4769329A (en) | Preparation of optically pure D- and L- lactic acid | |
| US3494832A (en) | Process for the manufacture of d-lactic acid and its salts | |
| US5360731A (en) | Bacteria capable of stereospecifically hydrolyzing R-(-)-2,2-dimethylcyclopropanecarboxamide | |
| NO319146B1 (no) | Mikrobiologisk fremgangsmate for fremstilling av heteroaromatiske karboksylsyrer og picolinsyre eller deres fysiologisk fordragelige salter ved hjelp av mikroorganismer fra slekten Alcaligenes | |
| US4745059A (en) | Process for the preparation of L-phenylalanine | |
| Behrendt et al. | The Production of l‐serine with a methylotrophic microorganism using the l‐serine pathway and coupling with an l‐tryptophan‐producing process | |
| HU217419B (hu) | Mikrobiológiai eljárás hidroxilcsoporttal helyettesített, aromás heterociklusos karbonsavak előállítására | |
| US5338667A (en) | Microbiological process for the production of malonyl-7-amino-cephalosporanic acid derivatives using Sphingomonas sp. DSM 7007 | |
| PL184111B1 (pl) | Mikrobiologiczny sposób wytwarzania heteroaromatycznych kwasów karboksylowych | |
| JP4269416B2 (ja) | α−ハロ−α，β−飽和カルボニル化合物の製造方法 | |
| US5234819A (en) | Method for preparing 2,5-diketo-D-gluconic acid | |
| JPH03112490A (ja) | Ｌ―ホモフェニルアラニンの製造方法 | |
| EP0643139A2 (en) | Process for preparing indigo | |
| CZ279298B6 (cs) | Mikroorganismy Alcaligenes faecalis DSM 6335 a způsob mikrobiologické výroby kyseliny 6-hydroxypikolinové | |
| JPWO2003062437A1 (ja) | α−ヒドロキシ酸アンモニウム塩の製造法 | |
| JPH0378999B2 (zh) | ||
| MXPA97002246A (en) | Process for producing aspartase and l-aspartic acid |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM1K | Lapsed by not paying the annual fees |