SK281873B6 - Spôsob mikrobiologickej výroby heteroaromatických karboxylových kyselín pomocou mikroorganizmov rodu alcaligenes - Google Patents
Spôsob mikrobiologickej výroby heteroaromatických karboxylových kyselín pomocou mikroorganizmov rodu alcaligenes Download PDFInfo
- Publication number
- SK281873B6 SK281873B6 SK716-96A SK71696A SK281873B6 SK 281873 B6 SK281873 B6 SK 281873B6 SK 71696 A SK71696 A SK 71696A SK 281873 B6 SK281873 B6 SK 281873B6
- Authority
- SK
- Slovakia
- Prior art keywords
- acid
- cyanopyridine
- microorganisms
- biotransformation
- production
- Prior art date
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- 244000005700 microbiome Species 0.000 title claims abstract description 23
- -1 heteroaromatic carboxylic acids Chemical class 0.000 title claims abstract description 16
- 241000588986 Alcaligenes Species 0.000 title claims abstract description 9
- 238000004519 manufacturing process Methods 0.000 title claims description 15
- 238000013048 microbiological method Methods 0.000 title 1
- 230000036983 biotransformation Effects 0.000 claims abstract description 24
- 238000000034 method Methods 0.000 claims abstract description 18
- 150000003839 salts Chemical class 0.000 claims abstract description 17
- 239000000758 substrate Substances 0.000 claims abstract description 15
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims abstract description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 7
- 235000000346 sugar Nutrition 0.000 claims abstract description 7
- 150000001735 carboxylic acids Chemical class 0.000 claims abstract description 6
- 238000006243 chemical reaction Methods 0.000 claims abstract description 6
- 230000002906 microbiologic effect Effects 0.000 claims abstract description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 3
- 125000005843 halogen group Chemical group 0.000 claims abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 2
- 150000003627 tricarboxylic acid derivatives Chemical class 0.000 claims abstract 2
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical compound OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 claims description 38
- FFNVQNRYTPFDDP-UHFFFAOYSA-N 2-cyanopyridine Chemical compound N#CC1=CC=CC=N1 FFNVQNRYTPFDDP-UHFFFAOYSA-N 0.000 claims description 24
- 229940081066 picolinic acid Drugs 0.000 claims description 19
- VRCWSYYXUCKEED-UHFFFAOYSA-N 6-Hydroxypicolinic acid Chemical compound OC(=O)C1=CC=CC(=O)N1 VRCWSYYXUCKEED-UHFFFAOYSA-N 0.000 claims description 16
- 241000588813 Alcaligenes faecalis Species 0.000 claims description 7
- OVBPIULPVIDEAO-LBPRGKRZSA-N folic acid Chemical compound C=1N=C2NC(N)=NC(=O)C2=NC=1CNC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 OVBPIULPVIDEAO-LBPRGKRZSA-N 0.000 claims 2
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- 229960000304 folic acid Drugs 0.000 claims 1
- 235000019152 folic acid Nutrition 0.000 claims 1
- 239000011724 folic acid Substances 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 2
- 239000000243 solution Substances 0.000 description 11
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 10
- 239000002609 medium Substances 0.000 description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 7
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- 230000015572 biosynthetic process Effects 0.000 description 6
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- 229940088710 antibiotic agent Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 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
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- 125000001246 bromo group Chemical group Br* 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
- PDEKDNMUYVDZCL-UHFFFAOYSA-N calcium;pyridine-2-carboxylic acid Chemical compound [Ca].OC(=O)C1=CC=CC=N1 PDEKDNMUYVDZCL-UHFFFAOYSA-N 0.000 description 1
- 229940041514 candida albicans extract Drugs 0.000 description 1
- 238000004113 cell culture Methods 0.000 description 1
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- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 150000001844 chromium Chemical class 0.000 description 1
- 229910052804 chromium Inorganic materials 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
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- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 1
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- 125000001153 fluoro group Chemical group F* 0.000 description 1
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- 125000002346 iodo group Chemical group I* 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
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- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
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- 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
- 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
- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride 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
- 239000007858 starting material Substances 0.000 description 1
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- 239000001384 succinic acid 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
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- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
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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
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- 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 (2)
| Publication Number | Publication Date |
|---|---|
| SK71696A3 SK71696A3 (en) | 1997-01-08 |
| SK281873B6 true SK281873B6 (sk) | 2001-08-06 |
Family
ID=25688320
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK716-96A SK281873B6 (sk) | 1995-06-07 | 1996-06-04 | Spôsob mikrobiologickej výroby heteroaromatických karboxylových kyselín pomocou mikroorganizmov rodu 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 |
| NO319146B1 (no) | 2005-06-27 |
| 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 |
| 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 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | Patent lapsed due to non-payment of maintenance fees |
Effective date: 20130604 |