SK279322B6 - Mikrobiologický spôsob hydroxylácie dusíkatých het - Google Patents
Mikrobiologický spôsob hydroxylácie dusíkatých het Download PDFInfo
- Publication number
- SK279322B6 SK279322B6 SK137-93A SK13793A SK279322B6 SK 279322 B6 SK279322 B6 SK 279322B6 SK 13793 A SK13793 A SK 13793A SK 279322 B6 SK279322 B6 SK 279322B6
- Authority
- SK
- Slovakia
- Prior art keywords
- acid
- microorganisms
- carboxylic acids
- nitrogenous
- hydroxy
- Prior art date
Links
- 244000005700 microbiome Species 0.000 title claims abstract description 29
- 238000000034 method Methods 0.000 title claims abstract description 19
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 title claims abstract description 8
- 150000001735 carboxylic acids Chemical class 0.000 title claims abstract 4
- 230000002906 microbiologic effect Effects 0.000 title claims description 6
- 230000033444 hydroxylation Effects 0.000 title claims 2
- 238000005805 hydroxylation reaction Methods 0.000 title claims 2
- -1 nitrogenous heterocyclic carboxylic acids Chemical class 0.000 title description 8
- 150000003839 salts Chemical class 0.000 claims abstract description 12
- RZOKQIPOABEQAM-UHFFFAOYSA-N 6-methylpyridine-3-carboxylic acid Chemical compound CC1=CC=C(C(O)=O)C=N1 RZOKQIPOABEQAM-UHFFFAOYSA-N 0.000 claims description 16
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- 239000000758 substrate Substances 0.000 claims description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 5
- AVFMENMETODLQX-UHFFFAOYSA-N 6-chloro-2-oxo-1h-pyrazine-3-carboxylic acid Chemical compound OC(=O)C1=NC=C(Cl)N=C1O AVFMENMETODLQX-UHFFFAOYSA-N 0.000 claims description 3
- KNZXPTJKLOLYKH-UHFFFAOYSA-N 6-methyl-2-oxo-1h-pyrazine-3-carboxylic acid Chemical compound CC1=CN=C(C(O)=O)C(O)=N1 KNZXPTJKLOLYKH-UHFFFAOYSA-N 0.000 claims description 3
- XRIHTJYXIHOBDQ-UHFFFAOYSA-N 6-methyl-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound CC1=CC=C(C(O)=O)C(=O)N1 XRIHTJYXIHOBDQ-UHFFFAOYSA-N 0.000 claims description 3
- 239000001963 growth medium Substances 0.000 claims description 3
- UQFORHXBOVBJQY-UHFFFAOYSA-N 5,6-dichloro-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound OC(=O)C1=CC(Cl)=C(Cl)N=C1O UQFORHXBOVBJQY-UHFFFAOYSA-N 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 7
- 238000013048 microbiological method Methods 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 10
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
- 239000002609 medium Substances 0.000 description 8
- 230000036983 biotransformation Effects 0.000 description 7
- 239000012153 distilled water Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 239000002253 acid Substances 0.000 description 6
- 229910052500 inorganic mineral Inorganic materials 0.000 description 6
- 239000011707 mineral Substances 0.000 description 6
- 239000011550 stock solution Substances 0.000 description 6
- 229960003512 nicotinic acid Drugs 0.000 description 5
- 235000001968 nicotinic acid Nutrition 0.000 description 5
- 239000011664 nicotinic acid Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- UEYQJQVBUVAELZ-UHFFFAOYSA-N 2-Hydroxynicotinic acid Chemical compound OC(=O)C1=CC=CN=C1O UEYQJQVBUVAELZ-UHFFFAOYSA-N 0.000 description 4
- 102000008109 Mixed Function Oxygenases Human genes 0.000 description 4
- 108010074633 Mixed Function Oxygenases Proteins 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 239000008363 phosphate buffer Substances 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- YBJHBAHKTGYVGT-ZKWXMUAHSA-N (+)-Biotin Chemical compound N1C(=O)N[C@@H]2[C@H](CCCCC(=O)O)SC[C@@H]21 YBJHBAHKTGYVGT-ZKWXMUAHSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 2
- 229920001817 Agar Polymers 0.000 description 2
- 239000002028 Biomass Substances 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound 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 2
- 239000008272 agar Substances 0.000 description 2
- RMRCNWBMXRMIRW-BYFNXCQMSA-M cyanocobalamin Chemical compound N#C[Co+]N([C@]1([H])[C@H](CC(N)=O)[C@]\2(CCC(=O)NC[C@H](C)OP(O)(=O)OC3[C@H]([C@H](O[C@@H]3CO)N3C4=CC(C)=C(C)C=C4N=C3)O)C)C/2=C(C)\C([C@H](C/2(C)C)CCC(N)=O)=N\C\2=C\C([C@H]([C@@]/2(CC(N)=O)C)CCC(N)=O)=N\C\2=C(C)/C2=N[C@]1(C)[C@@](C)(CC(N)=O)[C@@H]2CCC(N)=O RMRCNWBMXRMIRW-BYFNXCQMSA-M 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 239000002054 inoculum Substances 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- NIPZZXUFJPQHNH-UHFFFAOYSA-N pyrazine-2-carboxylic acid Chemical compound OC(=O)C1=CN=CC=N1 NIPZZXUFJPQHNH-UHFFFAOYSA-N 0.000 description 2
- 239000010802 sludge Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000002689 soil Substances 0.000 description 2
- 239000006228 supernatant Substances 0.000 description 2
- 108020004465 16S ribosomal RNA Proteins 0.000 description 1
- IBRSSZOHCGUTHI-UHFFFAOYSA-N 2-chloropyridine-3-carboxylic acid Chemical compound OC(=O)C1=CC=CN=C1Cl IBRSSZOHCGUTHI-UHFFFAOYSA-N 0.000 description 1
- RNRLTTNKVLFZJS-UHFFFAOYSA-N 5,6-dichloropyridine-3-carboxylic acid Chemical compound OC(=O)C1=CN=C(Cl)C(Cl)=C1 RNRLTTNKVLFZJS-UHFFFAOYSA-N 0.000 description 1
- FXJOTWLLDJYKAG-UHFFFAOYSA-N 5-chloropyrazine-2-carboxylic acid Chemical compound OC(=O)C1=CN=C(Cl)C=N1 FXJOTWLLDJYKAG-UHFFFAOYSA-N 0.000 description 1
- RBYJWCRKFLGNDB-UHFFFAOYSA-N 5-methylpyrazine-2-carboxylic acid Chemical compound CC1=CN=C(C(O)=O)C=N1 RBYJWCRKFLGNDB-UHFFFAOYSA-N 0.000 description 1
- UAWMVMPAYRWUFX-UHFFFAOYSA-N 6-Chloronicotinic acid Chemical compound OC(=O)C1=CC=C(Cl)N=C1 UAWMVMPAYRWUFX-UHFFFAOYSA-N 0.000 description 1
- YXUNFRVJLSKENL-UHFFFAOYSA-N 6-hydroxy-6-methyl-1h-pyridine-3-carboxylic acid Chemical compound CC1(O)NC=C(C(O)=O)C=C1 YXUNFRVJLSKENL-UHFFFAOYSA-N 0.000 description 1
- 102000004400 Aminopeptidases Human genes 0.000 description 1
- 108090000915 Aminopeptidases Proteins 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- 102000016938 Catalase Human genes 0.000 description 1
- 108010053835 Catalase Proteins 0.000 description 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
- 239000011665 D-biotin Substances 0.000 description 1
- 235000000638 D-biotin Nutrition 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 235000006679 Mentha X verticillata Nutrition 0.000 description 1
- 235000002899 Mentha suaveolens Nutrition 0.000 description 1
- 235000001636 Mentha x rotundifolia Nutrition 0.000 description 1
- 229910004616 Na2MoO4.2H2 O Inorganic materials 0.000 description 1
- BOAXSHKIRIUWHL-UHFFFAOYSA-N OC1=C(C(=O)O)C=CC(=N1)C.CC1=NC=C(C(=O)O)C=C1 Chemical compound OC1=C(C(=O)O)C=CC(=N1)C.CC1=NC=C(C(=O)O)C=C1 BOAXSHKIRIUWHL-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 238000012300 Sequence Analysis Methods 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 229960004050 aminobenzoic acid Drugs 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 238000004113 cell culture Methods 0.000 description 1
- 239000006285 cell suspension Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- 229960002104 cyanocobalamin Drugs 0.000 description 1
- 235000000639 cyanocobalamin Nutrition 0.000 description 1
- 239000011666 cyanocobalamin Substances 0.000 description 1
- 230000009089 cytolysis Effects 0.000 description 1
- 239000012737 fresh medium Substances 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-ZSJDYOACSA-N heavy water Substances [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- FCHXJFJNDJXENQ-UHFFFAOYSA-N pyridoxal hydrochloride Chemical compound Cl.CC1=NC=C(CO)C(C=O)=C1O FCHXJFJNDJXENQ-UHFFFAOYSA-N 0.000 description 1
- RADKZDMFGJYCBB-UHFFFAOYSA-N pyridoxal hydrochloride Natural products CC1=NC=C(CO)C(C=O)=C1O RADKZDMFGJYCBB-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 239000010865 sewage Substances 0.000 description 1
- 239000010801 sewage sludge Substances 0.000 description 1
- FDEIWTXVNPKYDL-UHFFFAOYSA-N sodium molybdate dihydrate Chemical compound O.O.[Na+].[Na+].[O-][Mo]([O-])(=O)=O FDEIWTXVNPKYDL-UHFFFAOYSA-N 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- RJURHSHUTWPPAM-UHFFFAOYSA-M sodium;6-methylpyridine-3-carboxylate Chemical compound [Na+].CC1=CC=C(C([O-])=O)C=N1 RJURHSHUTWPPAM-UHFFFAOYSA-M 0.000 description 1
- KFLRWGSAMLBHBV-UHFFFAOYSA-M sodium;pyridine-3-carboxylate Chemical compound [Na+].[O-]C(=O)C1=CC=CN=C1 KFLRWGSAMLBHBV-UHFFFAOYSA-M 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- DPJRMOMPQZCRJU-UHFFFAOYSA-M thiamine hydrochloride Chemical compound Cl.[Cl-].CC1=C(CCO)SC=[N+]1CC1=CN=C(C)N=C1N DPJRMOMPQZCRJU-UHFFFAOYSA-M 0.000 description 1
- 229960000344 thiamine hydrochloride Drugs 0.000 description 1
- 235000019190 thiamine hydrochloride Nutrition 0.000 description 1
- 239000011747 thiamine hydrochloride Substances 0.000 description 1
- 238000004809 thin layer chromatography 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
- C07D213/80—Acids; Esters in position 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D241/24—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S435/00—Chemistry: molecular biology and microbiology
- Y10S435/8215—Microorganisms
- Y10S435/822—Microorganisms using bacteria or actinomycetales
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Health & Medical Sciences (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- Microbiology (AREA)
- Biochemistry (AREA)
- General Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Tropical Medicine & Parasitology (AREA)
- Virology (AREA)
- Biomedical Technology (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Micro-Organisms Or Cultivation Processes Thereof (AREA)
- Pyridine Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH67292 | 1992-03-04 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SK13793A3 SK13793A3 (en) | 1993-10-06 |
| SK279322B6 true SK279322B6 (sk) | 1998-10-07 |
Family
ID=4192473
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK137-93A SK279322B6 (sk) | 1992-03-04 | 1993-02-25 | Mikrobiologický spôsob hydroxylácie dusíkatých het |
Country Status (17)
| Country | Link |
|---|---|
| US (2) | US5306630A (cs) |
| EP (1) | EP0559116B1 (cs) |
| JP (1) | JPH06199797A (cs) |
| KR (1) | KR100274205B1 (cs) |
| CN (1) | CN1077748A (cs) |
| AT (1) | ATE153698T1 (cs) |
| CA (1) | CA2091005C (cs) |
| CZ (1) | CZ282939B6 (cs) |
| DE (1) | DE59306547D1 (cs) |
| DK (1) | DK0559116T3 (cs) |
| ES (1) | ES2101887T3 (cs) |
| GE (1) | GEP19991710B (cs) |
| GR (1) | GR3024286T3 (cs) |
| LT (1) | LT3114B (cs) |
| LV (1) | LV10504B (cs) |
| RU (1) | RU2122029C1 (cs) |
| SK (1) | SK279322B6 (cs) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9426293D0 (en) * | 1994-12-28 | 1995-02-22 | Zeneca Ltd | Composition,compound and use |
| US5763232A (en) * | 1996-02-15 | 1998-06-09 | Mitsubishi Chemical Corporation | Method for producing 3-hydroxy nitrogen-containing six-membered cylic compound |
| US6767741B1 (en) * | 1999-08-27 | 2004-07-27 | Invitrogen Corporation | Metal binding compounds and their use in cell culture medium compositions |
| EP1210410B1 (en) * | 1999-08-27 | 2008-01-16 | Invitrogen Corporation | Metal binding compounds and their use in cell culture medium compositions |
| AU2002220603A1 (en) * | 2000-10-06 | 2002-04-15 | Lonza A.G. | Biotechnological method for preparing carboxylic acids with a hydroxy-nitrogen heterocycle |
| WO2009041473A1 (ja) * | 2007-09-27 | 2009-04-02 | Toyama Chemical Co., Ltd. | ６－フルオロ－３－ヒドロキシ－２－ピラジンカルボニトリルの有機アミン塩およびその製造法 |
| MX2013005179A (es) * | 2010-11-12 | 2013-07-05 | Fujifilm Corp | Derivado de pirazino[2,3-d]isoxazol. |
| KR102848894B1 (ko) * | 2022-10-26 | 2025-08-21 | 한국원자력연구원 | 합성 니코틴의 감별 방법 |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4081451A (en) * | 1975-03-20 | 1978-03-28 | Schering Corporation | Process for preparing 2-halogeno nicotinic acids |
| JPS6061567A (ja) * | 1983-09-14 | 1985-04-09 | ロンザ リミテツド | ２−ピリジンカルボン酸−ν−オキサイドから２−ヒドロキシピリジンを製造する方法 |
| CH658866A5 (de) * | 1984-02-21 | 1986-12-15 | Lonza Ag | Verfahren zur herstellung von 6-hydroxynikotinsaeure. |
| CH658867A5 (de) * | 1984-02-22 | 1986-12-15 | Lonza Ag | Verfahren zur herstellung von 6-hydroxynikotinsaeure. |
| IN170700B (cs) * | 1989-12-20 | 1992-05-02 | Lonza Ag | |
| US5236832A (en) * | 1990-02-13 | 1993-08-17 | Lonza, Ltd. | Microbiological oxidation of methyl groups in heterocycles |
| US5242816A (en) * | 1990-07-10 | 1993-09-07 | Lonza Ltd. | Microbiological oxidation of alkyl groups in heterocycles |
| CZ279464B6 (cs) * | 1990-09-24 | 1995-05-17 | Lonza A.G. | Způsob hydroxylace methylových skupin v aromatických heterocyklech, hybridní plasmidy pL05 a p L04 uložené v mikroorganismech Pseudomonas putida a Escherichia coli |
| CZ279488B6 (cs) * | 1990-09-25 | 1995-05-17 | Lonza A.G. | Způsob mikrobiologické výroby hydroxylovaných heterocyklů |
| KR100233330B1 (ko) * | 1991-02-04 | 1999-12-01 | 하인즈 모제르 | 6-히드록시피콜린산을 제조하기 위한 미생물학적 방법 |
| US5238830A (en) * | 1991-02-04 | 1993-08-24 | Lonza Ltd. | Microbiological process for the production of 6-hydroxypicolinic acid |
| JPH0728750B2 (ja) * | 1991-03-30 | 1995-04-05 | 池田食研株式会社 | 微生物によるピラジン酸の水酸化物の製造方法 |
| JPH0740951B2 (ja) * | 1991-03-30 | 1995-05-10 | 池田食研株式会社 | 微生物による含窒素複素環化合物の水酸化物の製造方法 |
| FI922125A7 (fi) * | 1991-06-21 | 1992-12-22 | Lonza Ag | Mikrobiologinen menetelmä 5-hydroksipyratsiinikarboksyylihapon valmistamiseksi |
| MX9204902A (es) * | 1991-08-30 | 1993-05-01 | Lonza Ag | Procedimiento microbiologico para la preparacion de acido 6-hidroxipirazincarboxilico. |
-
1993
- 1993-02-24 CZ CZ93272A patent/CZ282939B6/cs not_active IP Right Cessation
- 1993-02-25 SK SK137-93A patent/SK279322B6/sk unknown
- 1993-02-26 GE GEAP1993559A patent/GEP19991710B/en unknown
- 1993-03-01 RU RU93004665/13A patent/RU2122029C1/ru not_active IP Right Cessation
- 1993-03-01 ES ES93103221T patent/ES2101887T3/es not_active Expired - Lifetime
- 1993-03-01 AT AT93103221T patent/ATE153698T1/de not_active IP Right Cessation
- 1993-03-01 EP EP93103221A patent/EP0559116B1/de not_active Expired - Lifetime
- 1993-03-01 DK DK93103221.3T patent/DK0559116T3/da not_active Application Discontinuation
- 1993-03-01 DE DE59306547T patent/DE59306547D1/de not_active Expired - Fee Related
- 1993-03-02 US US08/024,768 patent/US5306630A/en not_active Expired - Fee Related
- 1993-03-02 LV LVP-93-162A patent/LV10504B/xx unknown
- 1993-03-03 LT LTIP377A patent/LT3114B/lt not_active IP Right Cessation
- 1993-03-03 CN CN93102666A patent/CN1077748A/zh active Pending
- 1993-03-04 KR KR1019930003372A patent/KR100274205B1/ko not_active Expired - Fee Related
- 1993-03-04 JP JP5043126A patent/JPH06199797A/ja active Pending
- 1993-03-04 CA CA002091005A patent/CA2091005C/en not_active Expired - Fee Related
- 1993-07-13 US US08/090,951 patent/US5364940A/en not_active Expired - Fee Related
-
1997
- 1997-07-30 GR GR970401935T patent/GR3024286T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| GEP19991710B (en) | 1999-08-05 |
| US5306630A (en) | 1994-04-26 |
| GR3024286T3 (en) | 1997-10-31 |
| US5364940A (en) | 1994-11-15 |
| DK0559116T3 (da) | 1997-06-16 |
| LT3114B (en) | 1994-12-27 |
| KR930019834A (ko) | 1993-10-19 |
| EP0559116B1 (de) | 1997-05-28 |
| CZ282939B6 (cs) | 1997-11-12 |
| LV10504B (en) | 1996-02-20 |
| LV10504A (lv) | 1995-02-20 |
| KR100274205B1 (ko) | 2000-12-15 |
| ATE153698T1 (de) | 1997-06-15 |
| CA2091005C (en) | 2001-09-25 |
| EP0559116A3 (en) | 1994-07-06 |
| CA2091005A1 (en) | 1993-09-05 |
| ES2101887T3 (es) | 1997-07-16 |
| DE59306547D1 (de) | 1997-07-03 |
| CN1077748A (zh) | 1993-10-27 |
| CZ27293A3 (en) | 1994-01-19 |
| EP0559116A2 (de) | 1993-09-08 |
| JPH06199797A (ja) | 1994-07-19 |
| LTIP377A (en) | 1994-06-15 |
| RU2122029C1 (ru) | 1998-11-20 |
| SK13793A3 (en) | 1993-10-06 |
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