JP2015091269A5 - - Google Patents
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- JP2015091269A5 JP2015091269A5 JP2015021874A JP2015021874A JP2015091269A5 JP 2015091269 A5 JP2015091269 A5 JP 2015091269A5 JP 2015021874 A JP2015021874 A JP 2015021874A JP 2015021874 A JP2015021874 A JP 2015021874A JP 2015091269 A5 JP2015091269 A5 JP 2015091269A5
- Authority
- JP
- Japan
- Prior art keywords
- polypeptide
- dichloro
- residue corresponding
- amino acid
- ketoreductase
- 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.)
- Granted
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- 229920001184 polypeptide Polymers 0.000 claims 26
- 102000004196 processed proteins & peptides Human genes 0.000 claims 26
- 108090000765 processed proteins & peptides Proteins 0.000 claims 26
- 101001110310 Lentilactobacillus kefiri NADP-dependent (R)-specific alcohol dehydrogenase Proteins 0.000 claims 13
- 239000000758 substrate Substances 0.000 claims 11
- 150000001413 amino acids Chemical group 0.000 claims 9
- JAOYKRSASYNDGH-BYPYZUCNSA-N (1s)-1-(2,6-dichloro-3-fluorophenyl)ethanol Chemical compound C[C@H](O)C1=C(Cl)C=CC(F)=C1Cl JAOYKRSASYNDGH-BYPYZUCNSA-N 0.000 claims 8
- VJBFZHHRVCPAPZ-UHFFFAOYSA-N 1-(2,6-dichloro-3-fluorophenyl)ethanone Chemical compound CC(=O)C1=C(Cl)C=CC(F)=C1Cl VJBFZHHRVCPAPZ-UHFFFAOYSA-N 0.000 claims 7
- 150000001875 compounds Chemical class 0.000 claims 6
- AGPKZVBTJJNPAG-WHFBIAKZSA-N L-isoleucine Chemical compound CC[C@H](C)[C@H](N)C(O)=O AGPKZVBTJJNPAG-WHFBIAKZSA-N 0.000 claims 5
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 claims 5
- AGPKZVBTJJNPAG-UHFFFAOYSA-N isoleucine Natural products CCC(C)C(N)C(O)=O AGPKZVBTJJNPAG-UHFFFAOYSA-N 0.000 claims 5
- 229960000310 isoleucine Drugs 0.000 claims 5
- 229930182817 methionine Natural products 0.000 claims 5
- 238000000034 method Methods 0.000 claims 5
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 claims 4
- AYFVYJQAPQTCCC-GBXIJSLDSA-N L-threonine Chemical compound C[C@@H](O)[C@H](N)C(O)=O AYFVYJQAPQTCCC-GBXIJSLDSA-N 0.000 claims 4
- KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 claims 4
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 claims 4
- AYFVYJQAPQTCCC-UHFFFAOYSA-N Threonine Natural products CC(O)C(N)C(O)=O AYFVYJQAPQTCCC-UHFFFAOYSA-N 0.000 claims 4
- 239000004473 Threonine Substances 0.000 claims 4
- KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Natural products CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 claims 4
- 235000004279 alanine Nutrition 0.000 claims 4
- 102000040430 polynucleotide Human genes 0.000 claims 4
- 108091033319 polynucleotide Proteins 0.000 claims 4
- 239000002157 polynucleotide Substances 0.000 claims 4
- 235000004400 serine Nutrition 0.000 claims 4
- 235000008521 threonine Nutrition 0.000 claims 4
- 239000004474 valine Substances 0.000 claims 4
- 235000014393 valine Nutrition 0.000 claims 4
- MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 claims 3
- 239000004475 Arginine Substances 0.000 claims 3
- XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 claims 3
- ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 claims 3
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 claims 3
- ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 claims 3
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 claims 3
- 238000006243 chemical reaction Methods 0.000 claims 3
- 235000018417 cysteine Nutrition 0.000 claims 3
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 claims 3
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 claims 3
- DCXYFEDJOCDNAF-UHFFFAOYSA-N Asparagine Natural products OC(=O)C(N)CC(N)=O DCXYFEDJOCDNAF-UHFFFAOYSA-N 0.000 claims 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims 2
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 claims 2
- DCXYFEDJOCDNAF-REOHCLBHSA-N L-asparagine Chemical compound OC(=O)[C@@H](N)CC(N)=O DCXYFEDJOCDNAF-REOHCLBHSA-N 0.000 claims 2
- QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical compound C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 claims 2
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 claims 2
- QIVBCDIJIAJPQS-UHFFFAOYSA-N Tryptophan Natural products C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 claims 2
- 125000000539 amino acid group Chemical group 0.000 claims 2
- 235000009582 asparagine Nutrition 0.000 claims 2
- 229960001230 asparagine Drugs 0.000 claims 2
- 239000013604 expression vector Substances 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 239000012453 solvate Substances 0.000 claims 2
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-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 1
- -1 6'-substituted acetophenone Chemical group 0.000 claims 1
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Natural products CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 claims 1
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 claims 1
- 239000004471 Glycine Substances 0.000 claims 1
- ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 claims 1
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims 1
- ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 claims 1
- HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 claims 1
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims 1
- 241000186660 Lactobacillus Species 0.000 claims 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims 1
- 239000004472 Lysine Substances 0.000 claims 1
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 claims 1
- 150000008062 acetophenones Chemical class 0.000 claims 1
- 235000013922 glutamic acid Nutrition 0.000 claims 1
- 239000004220 glutamic acid Substances 0.000 claims 1
- ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 claims 1
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 claims 1
- 229940039696 lactobacillus Drugs 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US97205807P | 2007-09-13 | 2007-09-13 | |
| US60/972,058 | 2007-09-13 |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010525057A Division JP5973131B2 (ja) | 2007-09-13 | 2008-09-13 | アセトフェノンの還元のためのケトレダクターゼポリペプチド |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016056646A Division JP2016105739A (ja) | 2007-09-13 | 2016-03-22 | アセトフェノンの還元のためのケトレダクターゼポリペプチド |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2015091269A JP2015091269A (ja) | 2015-05-14 |
| JP2015091269A5 true JP2015091269A5 (enExample) | 2015-07-16 |
| JP6137758B2 JP6137758B2 (ja) | 2017-05-31 |
Family
ID=40260827
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010525057A Active JP5973131B2 (ja) | 2007-09-13 | 2008-09-13 | アセトフェノンの還元のためのケトレダクターゼポリペプチド |
| JP2015021874A Active JP6137758B2 (ja) | 2007-09-13 | 2015-02-06 | アセトフェノンの還元のためのケトレダクターゼポリペプチド |
| JP2016056646A Withdrawn JP2016105739A (ja) | 2007-09-13 | 2016-03-22 | アセトフェノンの還元のためのケトレダクターゼポリペプチド |
| JP2018037319A Withdrawn JP2018086028A (ja) | 2007-09-13 | 2018-03-02 | アセトフェノンの還元のためのケトレダクターゼポリペプチド |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010525057A Active JP5973131B2 (ja) | 2007-09-13 | 2008-09-13 | アセトフェノンの還元のためのケトレダクターゼポリペプチド |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016056646A Withdrawn JP2016105739A (ja) | 2007-09-13 | 2016-03-22 | アセトフェノンの還元のためのケトレダクターゼポリペプチド |
| JP2018037319A Withdrawn JP2018086028A (ja) | 2007-09-13 | 2018-03-02 | アセトフェノンの還元のためのケトレダクターゼポリペプチド |
Country Status (6)
| Country | Link |
|---|---|
| US (12) | US8748143B2 (enExample) |
| EP (1) | EP2198018B1 (enExample) |
| JP (4) | JP5973131B2 (enExample) |
| KR (1) | KR101586503B1 (enExample) |
| CN (1) | CN101855342B (enExample) |
| WO (1) | WO2009036404A2 (enExample) |
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| CN101784669B (zh) | 2007-08-24 | 2015-02-18 | 科德克希思公司 | 用于(r)-3-羟基四氢噻吩的立体选择性制备的改善的酮还原酶多肽 |
| CN101855342B (zh) | 2007-09-13 | 2013-07-10 | 科德克希思公司 | 用于还原苯乙酮的酮还原酶多肽 |
| CN101889081B (zh) * | 2007-09-28 | 2014-06-18 | 科德克希思公司 | 酮还原酶多肽及其用途 |
| SI2205727T1 (sl) | 2007-10-01 | 2015-09-30 | Codexis, Inc. | Polipeptidi ketoreduktaze za izdelavo azetidinona |
| US8288141B2 (en) | 2008-08-27 | 2012-10-16 | Codexis, Inc. | Ketoreductase polypeptides for the production of 3-aryl-3-hydroxypropanamine from a 3-aryl-3-ketopropanamine |
| US8288131B2 (en) * | 2008-08-27 | 2012-10-16 | Codexis, Inc. | Ketoreductase polypeptides and uses thereof |
| SI2329013T1 (sl) | 2008-08-27 | 2016-03-31 | Codexis, Inc. | Polipeptidi ketoreduktaze za proizvodnjo 3-aril-3-hidroksipropanamina iz 3-aril-3-ketopropanamina |
| EP2329014B1 (en) | 2008-08-29 | 2014-10-22 | Codexis, Inc. | Ketoreductase polypeptides for the stereoselective production of (4s)-3[(5s)-5(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidin-2-one |
| WO2011022548A2 (en) | 2009-08-19 | 2011-02-24 | Codexis, Inc. | Ketoreductase polypeptides for the preparation of phenylephrine |
| EP2510089B1 (en) | 2009-12-08 | 2015-10-21 | Codexis, Inc. | Synthesis of prazole compounds |
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| WO2013062878A1 (en) | 2011-10-27 | 2013-05-02 | Merck Sharp & Dohme Corp. | Process for making beta 3 angonists and intermediates |
| JP6063948B2 (ja) | 2011-10-27 | 2017-01-18 | メルク・シャープ・アンド・ドーム・コーポレーションＭｅｒｃｋ Ｓｈａｒｐ ＆ Ｄｏｈｍｅ Ｃｏｒｐ． | ベータ３アゴニストおよび中間体を製造するプロセス |
| CN104053771B (zh) | 2011-11-18 | 2016-11-09 | 科德克希思公司 | 用于制备羟基取代的氨基甲酸酯的生物催化剂 |
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| LT2968269T (lt) | 2013-03-15 | 2019-10-25 | Merck Sharp & Dohme | Beta 3 agonistų ir tarpinių junginių gamybos būdas |
| WO2014150633A1 (en) | 2013-03-15 | 2014-09-25 | Merck Sharp & Dohme Corp. | Immobilized ketoreductases and process for making and using immobilized ketoreductase |
| AU2014306149B2 (en) | 2013-08-06 | 2019-09-19 | Imago Biosciences Inc. | KDM1A inhibitors for the treatment of disease |
| CN105765592B (zh) | 2013-09-27 | 2019-12-17 | 科德克希思公司 | 用于酶变体的自动筛选的方法、装置和系统 |
| HUE053379T2 (hu) | 2013-11-13 | 2021-06-28 | Codexis Inc | Génmódosított imin-reduktázok és eljárások keton és amin vegyületek reduktív aminálására |
| US10415023B2 (en) * | 2013-12-10 | 2019-09-17 | Amano Enzyme Inc. | Modified lipase and use thereof |
| CN104975048B (zh) * | 2014-04-02 | 2018-07-24 | 中国科学院过程工程研究所 | 梅岭霉素合成基因簇中酮还原酶MeiF在手性芳香醇生产中的应用 |
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| CA2968275C (en) | 2014-11-25 | 2023-09-12 | Codexis, Inc. | Engineered imine reductases and methods for the reductive amination of ketone and amine compounds |
| US10696953B2 (en) | 2015-02-10 | 2020-06-30 | Codexis, Inc. | Ketoreductase polypeptides for the synthesis of chiral compounds |
| MX387224B (es) | 2015-02-12 | 2025-03-18 | Imago Biosciences Inc | Inhibidores de kdm1a para el tratamiento de enfermedades. |
| CN104846025B (zh) * | 2015-03-31 | 2018-06-01 | 浙江大学 | 一种制备(2s，3r)-2-苯甲酰氨甲基-3-羟基丁酸甲酯的方法 |
| CN105906656B (zh) * | 2016-05-17 | 2018-01-23 | 凯莱英医药集团（天津）股份有限公司 | 一种克唑替尼中间体的合成方法 |
| CN106047950A (zh) * | 2016-06-30 | 2016-10-26 | 尚科生物医药（上海）有限公司 | 一种(s)‑1‑(2,6‑二氯‑3‑氟苯基)乙醇的生物制备方法 |
| WO2018035259A1 (en) | 2016-08-16 | 2018-02-22 | Imago Biosciences, Inc. | Methods and processes for the preparation of kdm1a inhibitors |
| WO2018035249A1 (en) * | 2016-08-16 | 2018-02-22 | Imago Biosciences, Inc. | Compositions and methods for producing stereoisomerically pure aminocyclopropanes |
| CN106636248A (zh) * | 2016-12-21 | 2017-05-10 | 浙江海洋大学 | 一种利用羰基还原酶制备克唑替尼中间体的方法 |
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| GB201802383D0 (en) * | 2018-02-14 | 2018-03-28 | Givaudan Sa | Process |
| CN108624603A (zh) * | 2018-03-30 | 2018-10-09 | 河北省科学院生物研究所 | 一种(s)-羰基还原酶及其编码基因与应用 |
| IL279260B2 (en) | 2018-05-11 | 2024-10-01 | Imago Biosciences Inc | Kdm1a inhibitors for the treatment of disease |
| KR20210032950A (ko) | 2018-07-16 | 2021-03-25 | 노파르티스 아게 | 페닐피페리디닐 인돌 유도체를 제조하기 위한 화학적 방법 |
| NZ774649A (en) | 2018-12-05 | 2025-07-25 | Urovant Sciences Gmbh | Vibegron for the treatment of overactive bladder symptoms |
| CN109706191B (zh) * | 2019-01-21 | 2022-09-09 | 南京欧信医药技术有限公司 | 一种托莫西汀中间体的酶催化合成方法 |
| EP3922728B1 (en) | 2019-04-19 | 2023-11-29 | API Corporation | Method for producing (1r,3r)-3-(trifluoromethyl)cyclohexan-1-ol and intermediate thereof |
| CN110218718A (zh) * | 2019-06-19 | 2019-09-10 | 南京趣酶生物科技有限公司 | 固定化酮还原酶突变体及其在制备奈必洛尔手性醇中间体及其类似物中的应用 |
| CN114555795B (zh) * | 2019-09-26 | 2025-05-27 | 科德克希思公司 | 酮还原酶多肽及多核苷酸 |
| CN111235123B (zh) * | 2020-03-27 | 2020-10-27 | 长兴制药股份有限公司 | 一种醇溶液高浓度耐受的羰基还原酶及其应用 |
| CN111718965A (zh) * | 2020-06-17 | 2020-09-29 | 宁波酶赛生物工程有限公司 | 一种(2s,3s)-2,3-丁二醇的制备方法 |
| CN115478059B (zh) * | 2021-05-31 | 2025-04-11 | 尚科生物医药（上海）有限公司 | 一种酮还原酶突变体及其应用 |
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