JP2010511394A5 - - Google Patents
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- Publication number
- JP2010511394A5 JP2010511394A5 JP2009539665A JP2009539665A JP2010511394A5 JP 2010511394 A5 JP2010511394 A5 JP 2010511394A5 JP 2009539665 A JP2009539665 A JP 2009539665A JP 2009539665 A JP2009539665 A JP 2009539665A JP 2010511394 A5 JP2010511394 A5 JP 2010511394A5
- Authority
- JP
- Japan
- Prior art keywords
- seq
- dehydrogenase
- secodione
- cofactor
- oxidoreductase
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 claims 20
- 101710088194 Dehydrogenase Proteins 0.000 claims 10
- 102000004316 Oxidoreductases Human genes 0.000 claims 8
- 108090000854 Oxidoreductases Proteins 0.000 claims 8
- 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 6
- 229930027945 nicotinamide-adenine dinucleotide Natural products 0.000 claims 6
- 238000006243 chemical reaction Methods 0.000 claims 5
- 229910052739 hydrogen Inorganic materials 0.000 claims 5
- 239000001257 hydrogen Substances 0.000 claims 5
- 108091028043 Nucleic acid sequence Proteins 0.000 claims 4
- 125000003275 alpha amino acid group Chemical group 0.000 claims 4
- 150000002431 hydrogen Chemical class 0.000 claims 4
- 150000007523 nucleic acids Chemical group 0.000 claims 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 3
- 150000001413 amino acids Chemical class 0.000 claims 3
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 claims 3
- 230000002255 enzymatic effect Effects 0.000 claims 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims 3
- 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 3
- 230000008929 regeneration Effects 0.000 claims 3
- 238000011069 regeneration method Methods 0.000 claims 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 2
- CETWDUZRCINIHU-UHFFFAOYSA-N 2-heptanol Chemical compound CCCCCC(C)O CETWDUZRCINIHU-UHFFFAOYSA-N 0.000 claims 2
- FWMNVWWHGCHHJJ-SKKKGAJSSA-N 4-amino-1-[(2r)-6-amino-2-[[(2r)-2-[[(2r)-2-[[(2r)-2-amino-3-phenylpropanoyl]amino]-3-phenylpropanoyl]amino]-4-methylpentanoyl]amino]hexanoyl]piperidine-4-carboxylic acid Chemical compound C([C@H](C(=O)N[C@H](CC(C)C)C(=O)N[C@H](CCCCN)C(=O)N1CCC(N)(CC1)C(O)=O)NC(=O)[C@H](N)CC=1C=CC=CC=1)C1=CC=CC=C1 FWMNVWWHGCHHJJ-SKKKGAJSSA-N 0.000 claims 2
- 102000004190 Enzymes Human genes 0.000 claims 2
- 108090000790 Enzymes Proteins 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- QNVRIHYSUZMSGM-UHFFFAOYSA-N hexan-2-ol Chemical compound CCCCC(C)O QNVRIHYSUZMSGM-UHFFFAOYSA-N 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- SJWFXCIHNDVPSH-UHFFFAOYSA-N octan-2-ol Chemical compound CCCCCCC(C)O SJWFXCIHNDVPSH-UHFFFAOYSA-N 0.000 claims 2
- JYVLIDXNZAXMDK-UHFFFAOYSA-N pentan-2-ol Chemical compound CCCC(C)O JYVLIDXNZAXMDK-UHFFFAOYSA-N 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 claims 1
- QNVRIHYSUZMSGM-LURJTMIESA-N 2-Hexanol Natural products CCCC[C@H](C)O QNVRIHYSUZMSGM-LURJTMIESA-N 0.000 claims 1
- OMXFYKCGCDGYNC-SDNWHVSQSA-N 2-ethyl-2-[(2e)-2-(6-methoxy-3,4-dihydro-2h-naphthalen-1-ylidene)ethyl]cyclopentane-1,3-dione Chemical compound C\1CCC2=CC(OC)=CC=C2C/1=C/CC1(CC)C(=O)CCC1=O OMXFYKCGCDGYNC-SDNWHVSQSA-N 0.000 claims 1
- WVYWICLMDOOCFB-UHFFFAOYSA-N 4-methyl-2-pentanol Chemical compound CC(C)CC(C)O WVYWICLMDOOCFB-UHFFFAOYSA-N 0.000 claims 1
- ZDVJGWXFXGJSIU-UHFFFAOYSA-N 5-methylhexan-2-ol Chemical compound CC(C)CCC(C)O ZDVJGWXFXGJSIU-UHFFFAOYSA-N 0.000 claims 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- OSVMTWJCGUFAOD-KZQROQTASA-N formestane Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1O OSVMTWJCGUFAOD-KZQROQTASA-N 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- QQZOPKMRPOGIEB-UHFFFAOYSA-N n-butyl methyl ketone Natural products CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- 230000003647 oxidation Effects 0.000 claims 1
- 238000007254 oxidation reaction Methods 0.000 claims 1
- 125000006239 protecting group Chemical group 0.000 claims 1
- 150000003333 secondary alcohols Chemical class 0.000 claims 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT0202706A AT504542B1 (de) | 2006-12-07 | 2006-12-07 | Verfahren zur enantioselektiven enzymatischen reduktion von secodionderivaten |
| 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 |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011183849A Division JP5627546B2 (ja) | 2006-12-07 | 2011-08-25 | セコジオン誘導体のエナンチオ選択的な酵素的還元の方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2010511394A JP2010511394A (ja) | 2010-04-15 |
| JP2010511394A5 true JP2010511394A5 (enExample) | 2010-08-19 |
Family
ID=39492649
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009539665A Pending JP2010511394A (ja) | 2006-12-07 | 2007-12-07 | セコジオン誘導体のエナンチオ選択的な酵素的還元の方法 |
| JP2011183849A Expired - Fee Related JP5627546B2 (ja) | 2006-12-07 | 2011-08-25 | セコジオン誘導体のエナンチオ選択的な酵素的還元の方法 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011183849A Expired - Fee Related JP5627546B2 (ja) | 2006-12-07 | 2011-08-25 | セコジオン誘導体のエナンチオ選択的な酵素的還元の方法 |
Country Status (14)
| Country | Link |
|---|---|
| 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) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
-
2006
- 2006-12-07 AT AT0202706A patent/AT504542B1/de not_active IP Right Cessation
-
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
-
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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