JP5532337B2 - 発酵培地に担体として作用する固体吸着樹脂の提供によるトリシクロ化合物の生産及び抽出方法 - Google Patents
発酵培地に担体として作用する固体吸着樹脂の提供によるトリシクロ化合物の生産及び抽出方法 Download PDFInfo
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- JP5532337B2 JP5532337B2 JP2010519850A JP2010519850A JP5532337B2 JP 5532337 B2 JP5532337 B2 JP 5532337B2 JP 2010519850 A JP2010519850 A JP 2010519850A JP 2010519850 A JP2010519850 A JP 2010519850A JP 5532337 B2 JP5532337 B2 JP 5532337B2
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- resin
- tricyclo compound
- xad
- amberlite
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- 150000001875 compounds Chemical class 0.000 title claims description 84
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- 238000000855 fermentation Methods 0.000 title claims description 39
- 230000004151 fermentation Effects 0.000 title claims description 39
- 239000003463 adsorbent Substances 0.000 title claims 3
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- QJJXYPPXXYFBGM-LFZNUXCKSA-N Tacrolimus Chemical compound C1C[C@@H](O)[C@H](OC)C[C@@H]1\C=C(/C)[C@@H]1[C@H](C)[C@@H](O)CC(=O)[C@H](CC=C)/C=C(C)/C[C@H](C)C[C@H](OC)[C@H]([C@H](C[C@H]2C)OC)O[C@@]2(O)C(=O)C(=O)N2CCCC[C@H]2C(=O)O1 QJJXYPPXXYFBGM-LFZNUXCKSA-N 0.000 claims description 55
- QJJXYPPXXYFBGM-SHYZHZOCSA-N tacrolimus Natural products CO[C@H]1C[C@H](CC[C@@H]1O)C=C(C)[C@H]2OC(=O)[C@H]3CCCCN3C(=O)C(=O)[C@@]4(O)O[C@@H]([C@H](C[C@H]4C)OC)[C@@H](C[C@H](C)CC(=C[C@@H](CC=C)C(=O)C[C@H](O)[C@H]2C)C)OC QJJXYPPXXYFBGM-SHYZHZOCSA-N 0.000 claims description 53
- ZDQSOHOQTUFQEM-NURRSENYSA-N ascomycin Chemical compound C/C([C@H]1OC(=O)[C@@H]2CCCCN2C(=O)C(=O)[C@]2(O)O[C@@H]([C@H](C[C@H]2C)OC)[C@@H](OC)C[C@@H](C)C/C(C)=C/[C@H](C(C[C@H](O)[C@H]1C)=O)CC)=C\[C@@H]1CC[C@@H](O)[C@H](OC)C1 ZDQSOHOQTUFQEM-NURRSENYSA-N 0.000 claims description 40
- ZDQSOHOQTUFQEM-XCXYXIJFSA-N ascomycin Natural products CC[C@H]1C=C(C)C[C@@H](C)C[C@@H](OC)[C@H]2O[C@@](O)([C@@H](C)C[C@H]2OC)C(=O)C(=O)N3CCCC[C@@H]3C(=O)O[C@H]([C@H](C)[C@@H](O)CC1=O)C(=C[C@@H]4CC[C@@H](O)[C@H](C4)OC)C ZDQSOHOQTUFQEM-XCXYXIJFSA-N 0.000 claims description 40
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 34
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- 238000001179 sorption measurement Methods 0.000 claims description 16
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 12
- 238000000746 purification Methods 0.000 claims description 12
- 239000007864 aqueous solution Substances 0.000 claims description 10
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
- 241000187747 Streptomyces Species 0.000 claims description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 6
- 238000011084 recovery Methods 0.000 claims description 6
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
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- CHRJZRDFSQHIFI-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;styrene Chemical compound C=CC1=CC=CC=C1.C=CC1=CC=CC=C1C=C CHRJZRDFSQHIFI-UHFFFAOYSA-N 0.000 claims description 2
- 229910019093 NaOCl Inorganic materials 0.000 claims description 2
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 claims description 2
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- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- 241000187391 Streptomyces hygroscopicus Species 0.000 description 4
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- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
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- 108091011114 FK506 binding proteins Proteins 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 244000046052 Phaseolus vulgaris Species 0.000 description 2
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- ZAHRKKWIAAJSAO-UHFFFAOYSA-N rapamycin Natural products COCC(O)C(=C/C(C)C(=O)CC(OC(=O)C1CCCCN1C(=O)C(=O)C2(O)OC(CC(OC)C(=CC=CC=CC(C)CC(C)C(=O)C)C)CCC2C)C(C)CC3CCC(O)C(C3)OC)C ZAHRKKWIAAJSAO-UHFFFAOYSA-N 0.000 description 2
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- 229930105110 Cyclosporin A Natural products 0.000 description 1
- PMATZTZNYRCHOR-CGLBZJNRSA-N Cyclosporin A Chemical compound CC[C@@H]1NC(=O)[C@H]([C@H](O)[C@H](C)C\C=C\C)N(C)C(=O)[C@H](C(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)N(C)C(=O)CN(C)C1=O PMATZTZNYRCHOR-CGLBZJNRSA-N 0.000 description 1
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 241000905500 Streptomyces hygroscopicus subsp. ascomyceticus Species 0.000 description 1
- 241000531819 Streptomyces venezuelae Species 0.000 description 1
- 108010027179 Tacrolimus Binding Proteins Proteins 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
- C12P17/18—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms containing at least two hetero rings condensed among themselves or condensed with a common carbocyclic ring system, e.g. rifamycin
-
- 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
- C12P17/18—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms containing at least two hetero rings condensed among themselves or condensed with a common carbocyclic ring system, e.g. rifamycin
- C12P17/188—Heterocyclic compound containing in the condensed system at least one hetero ring having nitrogen atoms and oxygen atoms as the only ring heteroatoms
Description
(ただし、前記化1において、R1は、ヒドロキシ基又は保護されたヒドロキシ基、R2は、水素、ヒドロキシ基又は保護されたヒドロキシ基、R3は、メチル、エチル、プロピル又はアリル基、nは1又は2、実線及び点線で二重に表示された部位は、単一結合又は二重結合を示す。)
Claims (9)
- ストレプトマイセス属に属するトリシクロ化合物生産菌株の発酵及び精製時、前記トリシクロ化合物生産菌株に疎水性吸着樹脂を加えて培養し、前記疎水性吸着樹脂を回収し、前記疎水性吸着樹脂からトリシクロ化合物を回収することを特徴とする、疎水性吸着樹脂を加えて生産収率及び精製効率を向上させるトリシクロ化合物生産方法であって、
前記トリシクロ化合物が、FK506及びFK520のうち1種以上であることを特徴とする、トリシクロ化合物生産方法。 - 前記疎水性吸着樹脂は、スチレン/ジビニルベンゼン重合体及び脂肪族エステル重合体を主要成分とする樹脂であることを特徴とする、請求項1に記載のトリシクロ化合物生産方法。
- 前記疎水性吸着樹脂は、 Diaion(登録商標) HP―20、Amberlite(登録商標) XAD(登録商標)―2、Amberlite(登録商標) XAD(登録商標)―4、Amberlite(登録商標) XAD(登録商標)―7、Amberlite(登録商標) XAD(登録商標)―7HP、Amberlite(登録商標) XAD(登録商標)―8、Amberlite(登録商標) XAD(登録商標)―16、Amberlite(登録商標) XAD(登録商標)―16 HP、Amberlite(登録商標) XAD(登録商標)―1180、Amberlite(登録商標) XAD(登録商標)―2000 及びAmberlite(登録商標) XAD(登録商標)―2010から選択される1種以上の樹脂であることを特徴とする、請求項1又は2に記載のトリシクロ化合物生産方法。
- 前記疎水性吸着樹脂が、3〜7%(v/v)であることを特徴とする、請求項1乃至3のうちいずれか一つの項に記載のトリシクロ化合物生産方法。
- 前記疎水性吸着樹脂が、培養開始後3日以内に添加することを特徴とする、請求項1に記載のトリシクロ化合物生産方法。
- 前記疎水性吸着樹脂から前記トリシクロ化合物を回収する段階において、前記トリシクロ化合物の回収に使用される溶出液が、アセトン、メタノール、エタノール、アセトニトリル、エチルアセテート、ヘキサン、クロロホルム、ジクロロメタンで構成されたグループから選択される1種以上であることを特徴とする、請求項1に記載のトリシクロ化合物生産方法。
- 前記溶出液が、50〜100%(v/v)のアセトン水溶液であることを特徴とする、請求項6に記載のトリシクロ化合物生産方法。
- 前記疎水性吸着樹脂が、再生して使用することを特徴とする、請求項1に記載のトリシクロ化合物生産方法。
- 前記疎水性吸着樹脂を50%イソプロピルアルコールと50%1N NaOH水溶液との混合溶媒、4%NaOCl水溶液及び蒸溜水で順次洗浄することを特徴とする、請求項8に記載のトリシクロ化合物生産方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR1020070082642A KR100891313B1 (ko) | 2007-08-17 | 2007-08-17 | 담체로 작용하는 흡착성 수지의 제공에 의한 트리사이클로화합물의 생산 및 추출 방법 |
KR10-2007-0082642 | 2007-08-17 | ||
PCT/KR2008/002520 WO2009025439A1 (en) | 2007-08-17 | 2008-05-06 | Method of extraction and yield-up of tricyclo compounds by adding a solid adsorbent resin as their carrier in fermentation medium |
Publications (2)
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JP2011505791A JP2011505791A (ja) | 2011-03-03 |
JP5532337B2 true JP5532337B2 (ja) | 2014-06-25 |
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JP2010519850A Active JP5532337B2 (ja) | 2007-08-17 | 2008-05-06 | 発酵培地に担体として作用する固体吸着樹脂の提供によるトリシクロ化合物の生産及び抽出方法 |
Country Status (5)
Country | Link |
---|---|
US (1) | US20110183385A1 (ja) |
EP (1) | EP2185714A4 (ja) |
JP (1) | JP5532337B2 (ja) |
KR (1) | KR100891313B1 (ja) |
WO (1) | WO2009025439A1 (ja) |
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CN102093378A (zh) * | 2010-12-21 | 2011-06-15 | 山东轻工业学院 | 一种从吸附树脂上高效解吸附埃博霉素的方法 |
CN102408435B (zh) * | 2011-07-18 | 2013-12-25 | 南京工业大学 | 一种从链霉菌发酵液中提纯子囊霉素的方法 |
CN107090477B (zh) * | 2017-05-04 | 2021-08-27 | 广州市微生物研究所有限公司 | 一种提高他克莫司产量的发酵方法 |
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IT1194181B (it) * | 1983-03-30 | 1988-09-14 | Erba Farmitalia | Procedimento migliorato per la purificazione della tilosina |
US4894366A (en) * | 1984-12-03 | 1990-01-16 | Fujisawa Pharmaceutical Company, Ltd. | Tricyclo compounds, a process for their production and a pharmaceutical composition containing the same |
US5126254A (en) * | 1990-01-24 | 1992-06-30 | Shin-Etsu Chemical Co., Ltd. | Process for preparation of streptovaricin |
US5194378A (en) * | 1991-01-28 | 1993-03-16 | Merck & Co., Inc. | Process for producing fk-506 |
US6909179B2 (en) | 1996-03-18 | 2005-06-21 | Renesas Technology Corp. | Lead frame and semiconductor device using the lead frame and method of manufacturing the same |
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US5968921A (en) | 1997-10-24 | 1999-10-19 | Orgegon Health Sciences University | Compositions and methods for promoting nerve regeneration |
WO1999047523A1 (de) * | 1998-03-17 | 1999-09-23 | GESELLSCHAFT FüR BIOTECHNOLOGISCHE FORSCHUNG MBH (GBF) | Apicularen a und b |
US6750047B2 (en) * | 2000-08-21 | 2004-06-15 | Kosan Biosciences, Inc. | Fermentation and purification of migrastatin and analog |
EP1458405A1 (en) | 2001-11-21 | 2004-09-22 | Sucampo AG | Use of fk506 and analogues for treating allergic diseases |
CA2494742C (en) * | 2002-07-29 | 2015-05-12 | Optimer Pharmaceuticals, Inc. | Tiacumicin production |
EP1536793A1 (en) | 2002-08-09 | 2005-06-08 | Sucampo Pharmaceuticals, Inc. | Pharmaceutical compositions comprising fk506 derivatives and the ir use for the treatment of allergic diseases |
ES2297481T3 (es) * | 2003-07-24 | 2008-05-01 | Teva Gyogyszergyar Zartkoruen Mukodo Reszvenytarsasag | Metodo para purificar macrolidos. |
KR100485877B1 (ko) | 2003-12-30 | 2005-04-28 | 종근당바이오 주식회사 | 타크롤리무스를 생산하는 미생물 및 이를 이용한타크롤리무스의 대량 생산방법 |
KR100652320B1 (ko) * | 2004-02-16 | 2006-11-29 | 근화제약주식회사 | 테이코플라닌의 분리 및 정제 방법 |
ITMI20042098A1 (it) * | 2004-11-03 | 2005-02-03 | Antibioticos Spa | Processo per la purificazione di tacrolimus |
-
2007
- 2007-08-17 KR KR1020070082642A patent/KR100891313B1/ko active IP Right Grant
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2008
- 2008-05-06 JP JP2010519850A patent/JP5532337B2/ja active Active
- 2008-05-06 EP EP08753317.0A patent/EP2185714A4/en not_active Withdrawn
- 2008-05-06 US US12/672,479 patent/US20110183385A1/en not_active Abandoned
- 2008-05-06 WO PCT/KR2008/002520 patent/WO2009025439A1/en active Application Filing
Also Published As
Publication number | Publication date |
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KR100891313B1 (ko) | 2009-03-31 |
JP2011505791A (ja) | 2011-03-03 |
EP2185714A4 (en) | 2015-12-16 |
EP2185714A1 (en) | 2010-05-19 |
KR20090018298A (ko) | 2009-02-20 |
WO2009025439A1 (en) | 2009-02-26 |
US20110183385A1 (en) | 2011-07-28 |
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