JP6643987B2 - ケトン化合物およびアミン化合物の還元的アミノ化のための操作されたイミンレダクターゼおよび方法 - Google Patents

ケトン化合物およびアミン化合物の還元的アミノ化のための操作されたイミンレダクターゼおよび方法 Download PDF

Info

Publication number
JP6643987B2
JP6643987B2 JP2016529958A JP2016529958A JP6643987B2 JP 6643987 B2 JP6643987 B2 JP 6643987B2 JP 2016529958 A JP2016529958 A JP 2016529958A JP 2016529958 A JP2016529958 A JP 2016529958A JP 6643987 B2 JP6643987 B2 JP 6643987B2
Authority
JP
Japan
Prior art keywords
compound
polypeptide
seq
sequence
amino acid
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.)
Active
Application number
JP2016529958A
Other languages
English (en)
Japanese (ja)
Other versions
JP2016536990A5 (https=
JP2016536990A (ja
Inventor
ニコラス ジェイ． アガード，
ニコラス ジェイ． アガード，
オスカー アルビゾ，
オスカー アルビゾ，
メリッサ アン メイヨー，
メリッサ アン メイヨー，
マイナー， ステファニー ウン
マイナー， ステファニー ウン
ジェイムズ ニコラス リギンズ，
ジェイムズ ニコラス リギンズ，
ジェフリー シー． ムーア，
ジェフリー シー． ムーア，
Original Assignee
コデクシス， インコーポレイテッド
コデクシス， インコーポレイテッド
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by コデクシス， インコーポレイテッド, コデクシス， インコーポレイテッド filed Critical コデクシス， インコーポレイテッド
Publication of JP2016536990A publication Critical patent/JP2016536990A/ja
Publication of JP2016536990A5 publication Critical patent/JP2016536990A5/ja
Application granted granted Critical
Publication of JP6643987B2 publication Critical patent/JP6643987B2/ja
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
    • C07K14/195—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from bacteria
    • C07K14/305—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from bacteria from Micrococcaceae (F)
    • 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.)
    • C12N9/0012—Oxidoreductases (1.) acting on nitrogen containing compounds as donors (1.4, 1.5, 1.6, 1.7)
    • C12N9/0026—Oxidoreductases (1.) acting on nitrogen containing compounds as donors (1.4, 1.5, 1.6, 1.7) acting on CH-NH groups of donors (1.5)
    • C12N9/0028—Oxidoreductases (1.) acting on nitrogen containing compounds as donors (1.4, 1.5, 1.6, 1.7) acting on CH-NH groups of donors (1.5) with NAD or NADP as acceptor (1.5.1)
    • 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
    • C12P13/00—Preparation of nitrogen-containing organic compounds
    • C12P13/001—Amines; Imines
    • 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
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12Y—ENZYMES
    • C12Y105/00—Oxidoreductases acting on the CH-NH group of donors (1.5)
    • C12Y105/01—Oxidoreductases acting on the CH-NH group of donors (1.5) with NAD+ or NADP+ as acceptor (1.5.1)
    • C12Y105/01028—Opine dehydrogenase (1.5.1.28)

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Health & Medical Sciences (AREA)
  • Biochemistry (AREA)
  • General Engineering & Computer Science (AREA)
  • Microbiology (AREA)
  • Biotechnology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Molecular Biology (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Biomedical Technology (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Biophysics (AREA)
  • Micro-Organisms Or Cultivation Processes Thereof (AREA)
  • Enzymes And Modification Thereof (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
JP2016529958A 2013-11-13 2014-11-12 ケトン化合物およびアミン化合物の還元的アミノ化のための操作されたイミンレダクターゼおよび方法 Active JP6643987B2 (ja)

Applications Claiming Priority (7)

Application Number Priority Date Filing Date Title
US201361903772P 2013-11-13 2013-11-13
US61/903,772 2013-11-13
US201462022323P 2014-07-09 2014-07-09
US201462022315P 2014-07-09 2014-07-09
US62/022,323 2014-07-09
US62/022,315 2014-07-09
PCT/US2014/065259 WO2015073555A1 (en) 2013-11-13 2014-11-12 Engineered imine reductases and methods for the reductive amination of ketone and amine compounds

Publications (3)

Publication Number Publication Date
JP2016536990A JP2016536990A (ja) 2016-12-01
JP2016536990A5 JP2016536990A5 (https=) 2019-04-11
JP6643987B2 true JP6643987B2 (ja) 2020-02-12

Family

ID=53044107

Family Applications (1)

Application Number Title Priority Date Filing Date
JP2016529958A Active JP6643987B2 (ja) 2013-11-13 2014-11-12 ケトン化合物およびアミン化合物の還元的アミノ化のための操作されたイミンレダクターゼおよび方法

Country Status (9)

Country Link
US (5) US9822346B2 (https=)
EP (1) EP3068793B1 (https=)
JP (1) JP6643987B2 (https=)
CN (1) CN106232619B (https=)
CA (1) CA2929664C (https=)
DK (1) DK3068793T3 (https=)
HU (1) HUE053379T2 (https=)
IL (1) IL245453B (https=)
WO (1) WO2015073555A1 (https=)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
MX2012006936A (es) * 2009-12-17 2012-07-17 Pioneer Hi Bred Int Evento de maiz dp-004114-3 y metodos para su deteccion.
CN106232619B (zh) 2013-11-13 2022-09-09 科德克希思公司 工程化的亚胺还原酶和用于酮和胺化合物的还原胺化的方法
US10370648B2 (en) 2014-11-25 2019-08-06 Codexis, Inc. Engineered imine reductases and methods for the reductive amination of ketone and amine compounds
KR101761830B1 (ko) 2015-10-21 2017-07-26 주식회사 엘지화학 리간드 화합물, 올레핀 올리고머화용 촉매계, 및 이를 이용한 올레핀 올리고머화 방법
IL264686B2 (en) * 2016-08-26 2024-07-01 Codexis Inc Engineered imine reductases and methods for reversible amination of ketone and amine compounds
CN107384885B (zh) * 2017-09-05 2019-12-24 武汉大学 亚胺还原酶及其突变体在合成(s)-1-芳基-1，2，3，4-四氢异喹啉中的应用
CN108504701B (zh) * 2018-04-26 2021-05-14 中南林业科技大学 一种异丙甲草胺中间体的合成方法
HUE051799T2 (hu) 2018-11-16 2021-03-29 Zanoprima Lifesciences Ltd Eljárás (S)-nikotin elõállítására myosmine vegyületbõl
EP3963057A4 (en) * 2019-05-01 2023-06-14 Codexis, Inc. MANIPULATED IMINE REDUCTASES AND METHODS FOR THE REDUCTIVE AMINATION OF KETONE AND AMINE COMPOUNDS
CN116286700B (zh) * 2021-10-18 2025-10-03 迪嘉药业集团股份有限公司 一种亚胺还原酶突变体及用途
CN114717211B (zh) * 2022-03-23 2023-06-02 江苏集萃分子工程研究院有限公司 亚胺还原酶突变体m5及其在合成氮杂环手性胺中的应用
CN116814569B (zh) * 2023-05-30 2025-07-25 华东理工大学 一种催化活性提高的醇脱氢酶突变体、基因工程菌及其应用
CN119931979A (zh) * 2024-11-27 2025-05-06 南京药石科技股份有限公司 一种亚胺还原酶突变体及其应用

Family Cites Families (65)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5538867A (en) 1988-09-13 1996-07-23 Elf Aquitaine Process for the electrochemical regeneration of pyridine cofactors
KR100356926B1 (ko) 1993-09-07 2003-01-10 교와 핫꼬 고교 가부시끼가이샤 트랜스-4-히드록시-l-프롤린의제조법
US5605793A (en) 1994-02-17 1997-02-25 Affymax Technologies N.V. Methods for in vitro recombination
US6395547B1 (en) 1994-02-17 2002-05-28 Maxygen, Inc. Methods for generating polynucleotides having desired characteristics by iterative selection and recombination
US20060257890A1 (en) 1996-05-20 2006-11-16 Maxygen, Inc. Methods and compositions for cellular and metabolic engineering
US5837458A (en) 1994-02-17 1998-11-17 Maxygen, Inc. Methods and compositions for cellular and metabolic engineering
US6335160B1 (en) 1995-02-17 2002-01-01 Maxygen, Inc. Methods and compositions for polypeptide engineering
US6165793A (en) 1996-03-25 2000-12-26 Maxygen, Inc. Methods for generating polynucleotides having desired characteristics by iterative selection and recombination
US5928905A (en) 1995-04-18 1999-07-27 Glaxo Group Limited End-complementary polymerase reaction
US6406855B1 (en) 1994-02-17 2002-06-18 Maxygen, Inc. Methods and compositions for polypeptide engineering
US6309883B1 (en) 1994-02-17 2001-10-30 Maxygen, Inc. Methods and compositions for cellular and metabolic engineering
US6117679A (en) 1994-02-17 2000-09-12 Maxygen, Inc. Methods for generating polynucleotides having desired characteristics by iterative selection and recombination
US5834252A (en) 1995-04-18 1998-11-10 Glaxo Group Limited End-complementary polymerase reaction
US6995017B1 (en) 1994-02-17 2006-02-07 Maxygen, Inc. Methods for generating polynucleotides having desired characteristics by iterative selection and recombination
FI964808A0 (fi) 1994-06-03 1996-12-02 Novo Nordisk Biotech Inc Puhdistetut Myceliophthora lakkaasit ja niitä koodaavat nukleiinihapot
CN101659926A (zh) 1994-06-30 2010-03-03 诺沃奇梅兹有限公司 非毒性、非产毒性、非致病性镰孢属表达系统及所用启动子和终止子
FI104465B (fi) 1995-06-14 2000-02-15 Valio Oy Proteiinihydrolysaatteja allergioiden hoitamiseksi tai estämiseksi, niiden valmistus ja käyttö
US6506602B1 (en) 1996-03-25 2003-01-14 Maxygen, Inc. Methods for generating polynucleotides having desired characteristics by iterative selection and recombination
US6096548A (en) 1996-03-25 2000-08-01 Maxygen, Inc. Method for directing evolution of a virus
US7148054B2 (en) 1997-01-17 2006-12-12 Maxygen, Inc. Evolution of whole cells and organisms by recursive sequence recombination
US6326204B1 (en) 1997-01-17 2001-12-04 Maxygen, Inc. Evolution of whole cells and organisms by recursive sequence recombination
KR100570935B1 (ko) 1997-01-17 2006-04-13 맥시겐, 인크. 반복적 서열 재조합에 의한 전세포 및 유기체의 개량 방법
US6537746B2 (en) 1997-12-08 2003-03-25 Maxygen, Inc. Method for creating polynucleotide and polypeptide sequences
US6365408B1 (en) 1998-06-19 2002-04-02 Maxygen, Inc. Methods of evolving a polynucleotides by mutagenesis and recombination
US6495023B1 (en) 1998-07-09 2002-12-17 Michigan State University Electrochemical methods for generation of a biological proton motive force and pyridine nucleotide cofactor regeneration
JP4221100B2 (ja) 1999-01-13 2009-02-12 エルピーダメモリ株式会社 半導体装置
US6917882B2 (en) 1999-01-19 2005-07-12 Maxygen, Inc. Methods for making character strings, polynucleotides and polypeptides having desired characteristics
US6436675B1 (en) 1999-09-28 2002-08-20 Maxygen, Inc. Use of codon-varied oligonucleotide synthesis for synthetic shuffling
US6376246B1 (en) 1999-02-05 2002-04-23 Maxygen, Inc. Oligonucleotide mediated nucleic acid recombination
US6368861B1 (en) 1999-01-19 2002-04-09 Maxygen, Inc. Oligonucleotide mediated nucleic acid recombination
US7702464B1 (en) 2001-08-21 2010-04-20 Maxygen, Inc. Method and apparatus for codon determining
US6961664B2 (en) 1999-01-19 2005-11-01 Maxygen Methods of populating data structures for use in evolutionary simulations
US7024312B1 (en) 1999-01-19 2006-04-04 Maxygen, Inc. Methods for making character strings, polynucleotides and polypeptides having desired characteristics
ES2341217T3 (es) 1999-01-19 2010-06-17 Maxygen, Inc. Recombinacion de acidos nucleicos mediada por oligonucleotidos.
AU3391900A (en) 1999-03-05 2000-09-21 Maxygen, Inc. Encryption of traits using split gene sequences
EP1181356B1 (en) 1999-03-11 2005-12-07 Eastman Chemical Company Phosphine stabilizers for oxidoreductase enzymes
US7430477B2 (en) 1999-10-12 2008-09-30 Maxygen, Inc. Methods of populating data structures for use in evolutionary simulations
US6519065B1 (en) 1999-11-05 2003-02-11 Jds Fitel Inc. Chromatic dispersion compensation device
EP1272967A2 (en) 2000-03-30 2003-01-08 Maxygen, Inc. In silico cross-over site selection
AU2003211367A1 (en) 2002-02-28 2003-09-09 Mitsubishi Chemical Corporation Novel dehydrogenase and gene encoding the same
JP5319865B2 (ja) 2002-03-01 2013-10-16 コデクシス メイフラワー ホールディングス， エルエルシー 機能的生体分子を同定する方法、システム、およびソフトウェア
US7747391B2 (en) 2002-03-01 2010-06-29 Maxygen, Inc. Methods, systems, and software for identifying functional biomolecules
US20050084907A1 (en) 2002-03-01 2005-04-21 Maxygen, Inc. Methods, systems, and software for identifying functional biomolecules
EP1488335A4 (en) 2002-03-09 2006-11-15 Maxygen Inc OPTIMIZING CROSSOVER POINTS FOR THE ADJUSTED EVOLUTION
US7132267B2 (en) 2002-08-09 2006-11-07 Codexis, Inc. Enzymatic processes for the production of 4-substituted 3-hydroxybutyric acid derivatives and vicinal cyano, hydroxy substituted carboxylic acid esters
JP2007502124A (ja) 2003-08-11 2007-02-08 コデクシス， インコーポレイテッド 改良ケトレダクターゼポリペプチドおよび関連ポリヌクレオチド
JP2007502114A (ja) 2003-08-11 2007-02-08 コデクシス， インコーポレイテッド 改良されたグルコースデヒドロゲナーゼポリペプチドおよび関連ポリヌクレオチド
CA2535255A1 (en) 2003-08-11 2005-02-24 Codexis, Inc. Improved halohydrin dehalogenases and related polynucleotides
EP2115130B1 (en) 2007-02-08 2011-08-03 Codexis, Inc. Ketoreductases and uses thereof
EP2118281A2 (en) 2007-02-12 2009-11-18 Codexis, Inc. Structure-activity relationships
JP2010536385A (ja) 2007-08-24 2010-12-02 コデクシス， インコーポレイテッド （ｒ）−３−ヒドロキシチオランの立体選択的生成のための改善されたケトレダクターゼポリペプチド
EP2198018B1 (en) 2007-09-13 2013-11-20 Codexis, Inc. Ketoreductase polypeptides for the reduction of acetophenones
EP2203557B1 (en) 2007-09-28 2012-02-29 Codexis, Inc. Ketoreductase polypeptides and uses thereof
HUE027683T2 (en) 2007-10-01 2016-10-28 Codexis Inc Ketoreductase polypeptides for the production of azetidinone
CN102015711B (zh) 2008-04-29 2013-05-01 诺瓦提斯公司 用于治疗寄生虫病的螺-吲哚衍生物
US20090312196A1 (en) 2008-06-13 2009-12-17 Codexis, Inc. Method of synthesizing polynucleotide variants
DK3023494T3 (en) 2008-06-13 2019-02-25 Codexis Inc PROCEDURE FOR SYNTHESIS OF POLYNUCLEOTIDE VARIETIES
US8288131B2 (en) 2008-08-27 2012-10-16 Codexis, Inc. Ketoreductase polypeptides and uses thereof
EP2329013B1 (en) 2008-08-27 2015-10-28 Codexis, Inc. Ketoreductase polypeptides for the production of a 3-aryl-3-hydroxypropanamine from a 3-aryl-3-ketopropanamine
WO2010025287A2 (en) 2008-08-27 2010-03-04 Codexis, Inc. Ketoreductase polypeptides for the production of 3-aryl-3-hydroxypropanamine from a 3-aryl-3-ketopropanamine
US8273554B2 (en) 2008-08-29 2012-09-25 Codexis, Inc. Ketoreductase polypeptides for the stereoselective production of (4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidin-2-one
EP2330190A1 (en) * 2008-09-01 2011-06-08 Daicel Chemical Industries, Ltd. Process for production of optically active amine derivative
WO2010024445A1 (ja) * 2008-09-01 2010-03-04 ダイセル化学工業株式会社 光学活性なアミン誘導体を製造するための方法
HUE036947T2 (hu) * 2012-05-11 2018-08-28 Codexis Inc Átalakított iminreduktázok és eljárások keton- és aminvegyületek reduktív aminálására
CN106232619B (zh) 2013-11-13 2022-09-09 科德克希思公司 工程化的亚胺还原酶和用于酮和胺化合物的还原胺化的方法

Also Published As

Publication number Publication date
CN106232619A (zh) 2016-12-14
US11060072B2 (en) 2021-07-13
US9822346B2 (en) 2017-11-21
US20210301266A1 (en) 2021-09-30
US20250304924A1 (en) 2025-10-02
CA2929664A1 (en) 2015-05-21
US10407668B2 (en) 2019-09-10
CA2929664C (en) 2023-01-24
EP3068793A4 (en) 2017-09-20
EP3068793A1 (en) 2016-09-21
IL245453B (en) 2021-04-29
WO2015073555A1 (en) 2015-05-21
US20150132807A1 (en) 2015-05-14
US20180030419A1 (en) 2018-02-01
HUE053379T2 (hu) 2021-06-28
IL245453A0 (en) 2016-06-30
EP3068793B1 (en) 2021-02-17
US12312609B2 (en) 2025-05-27
DK3068793T3 (da) 2021-03-22
CN106232619B (zh) 2022-09-09
JP2016536990A (ja) 2016-12-01
US20190345458A1 (en) 2019-11-14

Similar Documents

Publication Publication Date Title
US10494656B2 (en) Engineered imine reductases and methods for the reductive amination of ketone and amine compounds
JP6643987B2 (ja) ケトン化合物およびアミン化合物の還元的アミノ化のための操作されたイミンレダクターゼおよび方法
US12378533B2 (en) Engineered imine reductases and methods for the reductive amination of ketone and amine compounds
JP2016536990A5 (https=)
JP7584804B2 (ja) 操作されたイミンレダクターゼ、ならびにケトンおよびアミン化合物の還元的アミノ化のための方法
JP2019526252A (ja) 操作されたイミンレダクターゼ、ならびにケトン化合物およびアミン化合物の還元的アミノ化のための方法
US20250129343A1 (en) Engineered glucose dehydrogenases and methods for the reductive amination of ketone and amine compounds

Legal Events

Date Code Title Description
A621 Written request for application examination

Free format text: JAPANESE INTERMEDIATE CODE: A621

Effective date: 20171025

A131 Notification of reasons for refusal

Free format text: JAPANESE INTERMEDIATE CODE: A131

Effective date: 20181129

A524 Written submission of copy of amendment under article 19 pct

Free format text: JAPANESE INTERMEDIATE CODE: A524

Effective date: 20190227

A131 Notification of reasons for refusal

Free format text: JAPANESE INTERMEDIATE CODE: A131

Effective date: 20190709

A521 Request for written amendment filed

Free format text: JAPANESE INTERMEDIATE CODE: A523

Effective date: 20190805

TRDD Decision of grant or rejection written
A01 Written decision to grant a patent or to grant a registration (utility model)

Free format text: JAPANESE INTERMEDIATE CODE: A01

Effective date: 20191225

A61 First payment of annual fees (during grant procedure)

Free format text: JAPANESE INTERMEDIATE CODE: A61

Effective date: 20200107

R150 Certificate of patent or registration of utility model

Ref document number: 6643987

Country of ref document: JP

Free format text: JAPANESE INTERMEDIATE CODE: R150

R250 Receipt of annual fees

Free format text: JAPANESE INTERMEDIATE CODE: R250

R250 Receipt of annual fees

Free format text: JAPANESE INTERMEDIATE CODE: R250

R250 Receipt of annual fees

Free format text: JAPANESE INTERMEDIATE CODE: R250