CA2671319C - Process for the enantioselective enzymatic reduction of secodione derivatives - Google Patents
Process for the enantioselective enzymatic reduction of secodione derivatives Download PDFInfo
- Publication number
- CA2671319C CA2671319C CA2671319A CA2671319A CA2671319C CA 2671319 C CA2671319 C CA 2671319C CA 2671319 A CA2671319 A CA 2671319A CA 2671319 A CA2671319 A CA 2671319A CA 2671319 C CA2671319 C CA 2671319C
- Authority
- CA
- Canada
- Prior art keywords
- seq
- secodione
- hydrogen
- oxidoreductase
- process according
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
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- 102000004316 Oxidoreductases Human genes 0.000 claims abstract description 52
- 238000006243 chemical reaction Methods 0.000 claims abstract description 32
- XJLXINKUBYWONI-DQQFMEOOSA-N [[(2r,3r,4r,5r)-5-(6-aminopurin-9-yl)-3-hydroxy-4-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(2s,3r,4s,5s)-5-(3-carbamoylpyridin-1-ium-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphate Chemical compound NC(=O)C1=CC=C[N+]([C@@H]2[C@H]([C@@H](O)[C@H](COP([O-])(=O)OP(O)(=O)OC[C@@H]3[C@H]([C@@H](OP(O)(O)=O)[C@@H](O3)N3C4=NC=NC(N)=C4N=C3)O)O2)O)=C1 XJLXINKUBYWONI-DQQFMEOOSA-N 0.000 claims abstract description 29
- 101710088194 Dehydrogenase Proteins 0.000 claims abstract description 27
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- 239000001257 hydrogen Substances 0.000 claims abstract description 26
- 230000002829 reductive effect Effects 0.000 claims abstract description 20
- BOPGDPNILDQYTO-NNYOXOHSSA-N nicotinamide-adenine dinucleotide Chemical compound C1=CCC(C(=O)N)=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OC[C@@H]2[C@H]([C@@H](O)[C@@H](O2)N2C3=NC=NC(N)=C3N=C2)O)O1 BOPGDPNILDQYTO-NNYOXOHSSA-N 0.000 claims abstract description 13
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Classifications
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- 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
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/24—Preparation of oxygen-containing organic compounds containing a carbonyl group
- C12P7/26—Ketones
- C12P7/38—Cyclopentanone- or cyclopentadione-containing products
-
- 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
- C12P33/00—Preparation of steroids
-
- 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
- C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
- C12N9/0004—Oxidoreductases (1.)
- C12N9/0006—Oxidoreductases (1.) acting on CH-OH groups as donors (1.1)
-
- 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
- C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
- C12N9/0004—Oxidoreductases (1.)
- C12N9/0008—Oxidoreductases (1.) acting on the aldehyde or oxo group of donors (1.2)
-
- 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
- C12P23/00—Preparation of compounds containing a cyclohexene ring having an unsaturated side chain containing at least ten carbon atoms bound by conjugated double bonds, e.g. carotenes
-
- 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
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Zoology (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Genetics & Genomics (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Microbiology (AREA)
- General Engineering & Computer Science (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Biomedical Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Enzymes And Modification Thereof (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Micro-Organisms Or Cultivation Processes Thereof (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT0202706A AT504542B1 (de) | 2006-12-07 | 2006-12-07 | Verfahren zur enantioselektiven enzymatischen reduktion von secodionderivaten |
| ATA2027/2006 | 2006-12-07 | ||
| PCT/EP2007/010640 WO2008068030A2 (de) | 2006-12-07 | 2007-12-07 | Verfahren zur herstellung von secolderivaten durch enantioselektive enzymatische reduktion von secodionderivaten unter verwendung einer oxidoreduktase/dehydrogenase in gegenwart von nadh oder nadph |
Publications (2)
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| CA2671319A1 CA2671319A1 (en) | 2008-06-12 |
| CA2671319C true CA2671319C (en) | 2016-02-23 |
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| CA2671319A Expired - Fee Related CA2671319C (en) | 2006-12-07 | 2007-12-07 | Process for the enantioselective enzymatic reduction of secodione derivatives |
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| US (2) | US20110020887A1 (enExample) |
| EP (2) | EP2087127B1 (enExample) |
| JP (2) | JP2010511394A (enExample) |
| KR (2) | KR101445191B1 (enExample) |
| CN (2) | CN101595224B (enExample) |
| AT (2) | AT504542B1 (enExample) |
| AU (1) | AU2007327842B2 (enExample) |
| CA (1) | CA2671319C (enExample) |
| ES (2) | ES2386380T3 (enExample) |
| HU (1) | HUE029907T2 (enExample) |
| PL (2) | PL2087127T3 (enExample) |
| PT (1) | PT2087127E (enExample) |
| WO (1) | WO2008068030A2 (enExample) |
| ZA (1) | ZA200904235B (enExample) |
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| TWI601825B (zh) | 2007-09-27 | 2017-10-11 | Ｉｅｐ有限公司 | 對映異構選擇性酶催化還原中間產物之方法 |
| CA2765566C (en) | 2009-06-22 | 2016-04-12 | Sk Biopharmaceuticals Co., Ltd. | Method for preparation of carbamic acid (r)-1-aryl-2-tetrazolyl-ethyl ester |
| US8404461B2 (en) | 2009-10-15 | 2013-03-26 | SK Biopharmaceutical Co. Ltd. | Method for preparation of carbamic acid (R)-1-aryl-2-tetrazolyl-ethyl ester |
| WO2013102619A2 (de) | 2012-01-04 | 2013-07-11 | C-Lecta Gmbh | Verfahren zur reduktion eines secodion-derivats mit einer alkoholdehydrogenase |
| DE102012017026A1 (de) | 2012-08-28 | 2014-03-06 | Forschungszentrum Jülich GmbH | Sensor für NADP(H) und Entwicklung von Alkoholdehydrogenasen |
| WO2018185304A1 (en) | 2017-04-07 | 2018-10-11 | Dsm Ip Assets B.V. | Regioselective hydroxylation of isophorone and further conversion to ketoisophorone |
| CN109112166B (zh) * | 2017-06-26 | 2023-08-15 | 弈柯莱生物科技(上海)股份有限公司 | 酶法制备替卡格雷中间体 |
| CN113025589B (zh) * | 2021-04-21 | 2023-04-07 | 重庆第二师范学院 | 3α-羟基类固醇脱氢酶、编码基因及其在催化剂中的应用 |
| WO2022238249A2 (en) * | 2021-05-11 | 2022-11-17 | Firmenich Sa | Process of making gingerol compounds and their use as flavor modifiers |
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| US1252524A (en) | 1917-04-21 | 1918-01-08 | Perry Wood W | Spring-latch protector. |
| GB1230455A (enExample) | 1967-05-22 | 1971-05-05 | ||
| DE1768985C3 (de) | 1967-07-24 | 1980-12-18 | Takeda Chemical Industries, Ltd., Osaka (Japan) | Verfahren zur Herstellung von optisch aktiven Steroid-Verbindungen, die einen am 13 ß -Kohlenstoffatom (C1 bis C4)alkylsubstituierten 17-Hydroxy-8,14-secogona-polyen- 14-on-kern enthalten |
| US3697379A (en) | 1970-04-28 | 1972-10-10 | American Home Prod | Asymmetric reduction of seco-steroids |
| DE4014573C1 (enExample) * | 1990-05-07 | 1991-10-10 | Forschungszentrum Juelich Gmbh, 5170 Juelich, De | |
| EP0630402B1 (de) * | 1992-03-13 | 1997-06-04 | Forschungszentrum Jülich Gmbh | Neue ketoester-reduktase, deren herstellung und verwendung für enzymatische redoxreaktionen |
| CA2103932A1 (en) * | 1992-11-05 | 1994-05-06 | Ramesh N. Patel | Stereoselective reduction of ketones |
| JP3574682B2 (ja) * | 1993-09-24 | 2004-10-06 | ダイセル化学工業株式会社 | 新規な酵素、該酵素を製造する方法、該酵素をコードするｄｎａ、該ｄｎａを含む形質転換体、該酵素による光学活性アルコール等の製造方法 |
| DE19610894A1 (de) | 1996-03-20 | 1997-09-25 | Leybold Ag | Vorrichtung zum Ziehen von Einkristallen aus einer in einem Tiegel befindlichen Schmelze |
| DE19610984A1 (de) | 1996-03-21 | 1997-09-25 | Boehringer Mannheim Gmbh | Alkohol-Dehydrogenase und deren Verwendung zur enzymatischen Herstellung chiraler Hydroxyverbindungen |
| SI20642A (sl) * | 1999-12-03 | 2002-02-28 | Kaneka Corporation | Nova karbonil-reduktaza, gen le-te in postopek za uporabo le-teh |
| DE10119274A1 (de) | 2001-04-20 | 2002-10-31 | Juelich Enzyme Products Gmbh | Enzymatisches Verfahren zur enantioselektiven Reduktion von Ketoverbindungen |
| DE10327454A1 (de) * | 2003-06-18 | 2005-01-20 | Juelich Enzyme Products Gmbh | Oxidoreduktase aus Pichia capsulata |
| AT501496B1 (de) * | 2005-02-21 | 2007-03-15 | Iep Gmbh | Verfahren zur enantioselektiven enzymatischen reduktion von ketoverbindungen |
| DE102005044736A1 (de) * | 2005-09-19 | 2007-03-22 | Basf Ag | Neue Dehydrogenasen, deren Derivate und ein Verfahren zur Herstellung von optisch aktiven Alkanolen |
| AT503017B1 (de) * | 2005-12-19 | 2007-07-15 | Iep Gmbh | Verfahren zur enantioselektiven enzymatischen reduktion von hydroxyketoverbindungen |
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2006
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2007
- 2007-12-07 ZA ZA200904235A patent/ZA200904235B/xx unknown
- 2007-12-07 AU AU2007327842A patent/AU2007327842B2/en not_active Ceased
- 2007-12-07 CN CN200780045107.6A patent/CN101595224B/zh not_active Expired - Fee Related
- 2007-12-07 ES ES07856445T patent/ES2386380T3/es active Active
- 2007-12-07 KR KR1020097014145A patent/KR101445191B1/ko not_active Expired - Fee Related
- 2007-12-07 PL PL07856445T patent/PL2087127T3/pl unknown
- 2007-12-07 WO PCT/EP2007/010640 patent/WO2008068030A2/de not_active Ceased
- 2007-12-07 PT PT07856445T patent/PT2087127E/pt unknown
- 2007-12-07 CA CA2671319A patent/CA2671319C/en not_active Expired - Fee Related
- 2007-12-07 JP JP2009539665A patent/JP2010511394A/ja active Pending
- 2007-12-07 EP EP07856445A patent/EP2087127B1/de not_active Not-in-force
- 2007-12-07 HU HUE11177932A patent/HUE029907T2/hu unknown
- 2007-12-07 PL PL11177932.8T patent/PL2410047T3/pl unknown
- 2007-12-07 EP EP11177932.8A patent/EP2410047B9/de active Active
- 2007-12-07 US US12/518,025 patent/US20110020887A1/en not_active Abandoned
- 2007-12-07 CN CN201110259204.3A patent/CN102382805B/zh not_active Expired - Fee Related
- 2007-12-07 KR KR1020117020658A patent/KR101474816B1/ko not_active Expired - Fee Related
- 2007-12-07 AT AT07856445T patent/ATE554181T1/de active
- 2007-12-07 ES ES11177932.8T patent/ES2588706T3/es active Active
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2011
- 2011-08-25 JP JP2011183849A patent/JP5627546B2/ja not_active Expired - Fee Related
- 2011-09-07 US US13/227,390 patent/US8323936B2/en not_active Expired - Fee Related
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