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WO2008153094A1 - アルカロイド類の生産方法 - Google Patents

アルカロイド類の生産方法 Download PDF

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Publication number
WO2008153094A1
WO2008153094A1 PCT/JP2008/060759 JP2008060759W WO2008153094A1 WO 2008153094 A1 WO2008153094 A1 WO 2008153094A1 JP 2008060759 W JP2008060759 W JP 2008060759W WO 2008153094 A1 WO2008153094 A1 WO 2008153094A1
Authority
WO
WIPO (PCT)
Prior art keywords
alkaloid
methyltransferase
production
norcoclaurine
methylcoclaurine
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.)
Ceased
Application number
PCT/JP2008/060759
Other languages
English (en)
French (fr)
Inventor
Fumihiko Sato
Hiromichi Minami
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Kyoto University NUC
Original Assignee
Kyoto University NUC
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 Kyoto University NUC filed Critical Kyoto University NUC
Priority to US12/664,142 priority Critical patent/US8993280B2/en
Priority to JP2009519300A priority patent/JP5177573B2/ja
Priority to EP08777168.9A priority patent/EP2169075B1/en
Publication of WO2008153094A1 publication Critical patent/WO2008153094A1/ja
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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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
    • 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
    • C12P17/12—Nitrogen as only ring hetero atom containing a six-membered hetero ring
    • 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
    • C12N15/00—Mutation or genetic engineering; DNA or RNA concerning genetic engineering, vectors, e.g. plasmids, or their isolation, preparation or purification; Use of hosts therefor
    • C12N15/09—Recombinant DNA-technology
    • C12N15/63—Introduction of foreign genetic material using vectors; Vectors; Use of hosts therefor; Regulation of expression
    • C12N15/70—Vectors or expression systems specially adapted for E. coli
    • 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
    • C12N15/00—Mutation or genetic engineering; DNA or RNA concerning genetic engineering, vectors, e.g. plasmids, or their isolation, preparation or purification; Use of hosts therefor
    • C12N15/09—Recombinant DNA-technology
    • C12N15/63—Introduction of foreign genetic material using vectors; Vectors; Use of hosts therefor; Regulation of expression
    • C12N15/79—Vectors or expression systems specially adapted for eukaryotic hosts
    • C12N15/80—Vectors or expression systems specially adapted for eukaryotic hosts for fungi
    • C12N15/81—Vectors or expression systems specially adapted for eukaryotic hosts for fungi for yeasts
    • 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
    • C12N15/00—Mutation or genetic engineering; DNA or RNA concerning genetic engineering, vectors, e.g. plasmids, or their isolation, preparation or purification; Use of hosts therefor
    • C12N15/09—Recombinant DNA-technology
    • C12N15/63—Introduction of foreign genetic material using vectors; Vectors; Use of hosts therefor; Regulation of expression
    • C12N15/79—Vectors or expression systems specially adapted for eukaryotic hosts
    • C12N15/82—Vectors or expression systems specially adapted for eukaryotic hosts for plant cells, e.g. plant artificial chromosomes (PACs)
    • C12N15/8241—Phenotypically and genetically modified plants via recombinant DNA technology
    • C12N15/8242—Phenotypically and genetically modified plants via recombinant DNA technology with non-agronomic quality (output) traits, e.g. for industrial processing; Value added, non-agronomic traits
    • C12N15/8243—Phenotypically and genetically modified plants via recombinant DNA technology with non-agronomic quality (output) traits, e.g. for industrial processing; Value added, non-agronomic traits involving biosynthetic or metabolic pathways, i.e. metabolic engineering, e.g. nicotine, caffeine

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Engineering & Computer Science (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Biotechnology (AREA)
  • Zoology (AREA)
  • Wood Science & Technology (AREA)
  • General Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Biomedical Technology (AREA)
  • Microbiology (AREA)
  • Molecular Biology (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Biophysics (AREA)
  • Physics & Mathematics (AREA)
  • Plant Pathology (AREA)
  • Mycology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nutrition Science (AREA)
  • Cell Biology (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Micro-Organisms Or Cultivation Processes Thereof (AREA)

Abstract

　本発明は、基質であるドーパミンを、モノアミンオキシダーゼ、ノルコクラウリン6-O-メチルトランスフェラーゼ、コクラウリン-N-メチルトランスフェラーゼおよび3'-ヒドロキシ-N-メチルコクラウリン-4'-O-メチルトランスフェラーゼの作用に供することを含む、アルカロイド類、例えば、レチクリンを生産する方法を提供する。
PCT/JP2008/060759 2007-06-12 2008-06-12 アルカロイド類の生産方法 Ceased WO2008153094A1 (ja)

Priority Applications (3)

Application Number Priority Date Filing Date Title
US12/664,142 US8993280B2 (en) 2007-06-12 2008-06-12 Method for producing alkaloids
JP2009519300A JP5177573B2 (ja) 2007-06-12 2008-06-12 アルカロイド類の生産方法
EP08777168.9A EP2169075B1 (en) 2007-06-12 2008-06-12 Method for production of alkaloid

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2007-155069 2007-06-12
JP2007155069 2007-06-12

Publications (1)

Publication Number Publication Date
WO2008153094A1 true WO2008153094A1 (ja) 2008-12-18

Family

ID=40129699

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2008/060759 Ceased WO2008153094A1 (ja) 2007-06-12 2008-06-12 アルカロイド類の生産方法

Country Status (4)

Country Link
US (1) US8993280B2 (ja)
EP (1) EP2169075B1 (ja)
JP (1) JP5177573B2 (ja)
WO (1) WO2008153094A1 (ja)

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012039438A1 (ja) * 2010-09-22 2012-03-29 石川県公立大学法人 植物ベンジルイソキノリンアルカロイドの生産方法
US20140134689A1 (en) * 2011-03-28 2014-05-15 The Regents Of The University Of California Host Cells and Methods for Oxidizing Aromatic Amino Acids
US20160251688A1 (en) 2013-11-04 2016-09-01 The Board Of Trustees Of The Leland Stanford Junior University Benzylisoquinoline alkaloid (bia) precursor producing microbes, and methods of making and using the same
US20160304923A1 (en) 2006-10-19 2016-10-20 California Institute Of Technology Compositions and methods for producing benzylisoquinoline alkaloids
US9534241B2 (en) 2013-03-15 2017-01-03 The Board Of Trustees Of The Leland Stanford Junior University Benzylisoquinoline alkaloids (BIA) producing microbes, and methods of making and using the same
US10519453B2 (en) 2015-05-04 2019-12-31 The Board Of Trustees Of The Leland Stanford Junior University Benzylisoquinoline alkaloid (BIA) precursor producing microbes, and methods of making and using the same
US10544420B2 (en) 2017-08-03 2020-01-28 Antheia, Inc. Engineered benzylisoquinoline alkaloid epimerases and methods of producing benzylisoquinoline alkaloids
WO2020090940A1 (ja) * 2018-10-30 2020-05-07 国立大学法人神戸大学 ベンジルイソキノリンアルカロイド（ｂｉａ）産生用の組換え宿主細胞及びベンジルイソキノリンアルカロイド（ｂｉａ）の新規製造方法
US11859225B2 (en) 2015-05-08 2024-01-02 The Board Of Trustees Of The Leland Stanford Junior University Methods of producing epimerases and benzylisoquinoline alkaloids
US12480131B2 (en) 2019-03-08 2025-11-25 The Board Of Trustees Of The Leland Stanford Junior University Tropane alkaloid (TA) producing non-plant host cells, and methods of making and using the same
US12497638B2 (en) 2023-10-23 2025-12-16 The Board Of Trustees Of The Leland Stanford Junior University Methods of producing epimerases and benzylisoquinoline alkaloids

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
HUE044896T2 (hu) * 2010-06-22 2019-11-28 Sun Pharmaceutical Industries Australia Pty Ltd Metil-transzferáz nukleinsavak és polipeptidek
EP2596012B1 (en) 2010-07-22 2017-12-06 Sun Pharmaceutical Industries (Australia) Pty Limited Plant cytochrome p450
GB201204407D0 (en) 2012-03-13 2012-04-25 Glaxosmithkline Australia Pty Ltd Nucleic acid molecule
CA2952638C (en) * 2014-06-19 2024-04-09 Epimeron Inc. Compositions and methods for making (s)-norcoclaurine and (s)-norlaudanosoline, and synthesis intermediates thereof
EP3529355A4 (en) 2016-10-18 2020-07-08 Antheia, Inc. PROCESSES FOR THE PRODUCTION OF NOR-OPIOID AND NAL-OPIOID BENZYLISOQUINOLINE ALKALOIDS

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH11178579A (ja) * 1997-12-24 1999-07-06 Mitsui Chem Inc （ｓ）−３’−ヒドロキシ−ｎ−メチルコクラウリン４’−ｏ−メチルトランスフェラーゼおよび該酵素遺伝子
JPH11178577A (ja) * 1997-12-24 1999-07-06 Mitsui Chem Inc ノルコクラウリン６−ｏ−メチルトランスフェラーゼおよび該酵素遺伝子
JP2002291487A (ja) * 2000-12-15 2002-10-08 Mitsui Chemicals Inc コクラウリン−ｎ−メチルトランスフェラーゼ
JP2004121233A (ja) * 2002-09-05 2004-04-22 Univ Kyoto イソキノリンアルカロイドの生合成に関与する遺伝子断片としてのポリヌクレオチド、そのポリヌクレオチドを含むｃＤＮＡライブラリー、及びそのポリヌクレオチドを用いて単離されたイソキノリンアルカロイド生合成に関与する全長遺伝子とタンパク質、その単離方法、並びにその形質転換体
JP2004141019A (ja) * 2002-10-22 2004-05-20 Univ Kyoto ノルコクラウリン６−ｏ−メチルトランスフェラーゼ遺伝子が導入された形質転換植物、及び、その形質転換植物を用いたイソキノリンアルカロイド生合成の誘導方法
WO2005003305A2 (en) 2003-06-19 2005-01-13 Exelixis, Inc. Usps as modifiers of the beta catenin pathway and methods of use

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6506378B1 (en) * 1998-12-16 2003-01-14 Arch Development Corporation Vesicular monoamine transporter gene therapy in Parkinson's disease

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH11178579A (ja) * 1997-12-24 1999-07-06 Mitsui Chem Inc （ｓ）−３’−ヒドロキシ−ｎ−メチルコクラウリン４’−ｏ−メチルトランスフェラーゼおよび該酵素遺伝子
JPH11178577A (ja) * 1997-12-24 1999-07-06 Mitsui Chem Inc ノルコクラウリン６−ｏ−メチルトランスフェラーゼおよび該酵素遺伝子
JP2002291487A (ja) * 2000-12-15 2002-10-08 Mitsui Chemicals Inc コクラウリン−ｎ−メチルトランスフェラーゼ
JP2004121233A (ja) * 2002-09-05 2004-04-22 Univ Kyoto イソキノリンアルカロイドの生合成に関与する遺伝子断片としてのポリヌクレオチド、そのポリヌクレオチドを含むｃＤＮＡライブラリー、及びそのポリヌクレオチドを用いて単離されたイソキノリンアルカロイド生合成に関与する全長遺伝子とタンパク質、その単離方法、並びにその形質転換体
JP2004141019A (ja) * 2002-10-22 2004-05-20 Univ Kyoto ノルコクラウリン６−ｏ−メチルトランスフェラーゼ遺伝子が導入された形質転換植物、及び、その形質転換植物を用いたイソキノリンアルカロイド生合成の誘導方法
WO2005003305A2 (en) 2003-06-19 2005-01-13 Exelixis, Inc. Usps as modifiers of the beta catenin pathway and methods of use

Non-Patent Citations (25)

* Cited by examiner, † Cited by third party
Title
ALLEN, R.S. ET AL.: "RNAi-mediated replacement of morphine with the nonnarcotic alkaloid reticuline in opium poppy", NAT. BIOTECHNOL., vol. 22, 2004, pages 1559 - 1566, XP008075878, DOI: doi:10.1038/nbt1033
CHOI, K.B. ET AL., JOURNAL OF BIOLOGICAL CHEMISTRY, vol. 277, 2002, pages 830 - 835
FUJII, N.; INUI, T.; IWASA, K.; MORISHIGE, T.; SATO, F.: "Knockdown of berberine bridge enzyme by RNAi accumulates (S)-reticuline and activates a silent pathway in cultured California poppy cells", TRANSGENIC RESEARCH, vol. 16, 2007, pages 363 - 375, XP019509127
IKEZAWA ET AL.: "Molecular cloning and characterization of CYP80G2, a cytochrome P450 which characterizes an intramolecular C-C phenol coupling of (S)-reticuline in magnoflorine biosynthesis, from cultured Coptis japonica cells", J BIOL CHEM, 2008
IKEZAWA N ET AL.: "Molecular cloning and characterization of CYP719, a methylenedioxy bridge-forming enzyme that belongs to a novel P450 family, from cultured Coptis japonica cells", J BIOL CHEM, vol. 278, 2003, pages 38557 - 38565, XP002313984, DOI: doi:10.1074/jbc.M302470200
IKEZAWA, N.; IWASA, K.; SATO, F.: "Molecular cloning and characterization of CYP80G2, a cytochrome P450 that catalyzes an intramolecular C-C phenol coupling of (S)-reticuline in magnoflorine biosynthesis, from cultured Coptis japonica cells", J. BIOL. CHEM., vol. 283, 2008, pages 8810 - 8821
ITO H; FUKUDA Y; MURATA K; KIMURA A: "Transformation of intact yeast cells treated with alkali cations", J BACTERIOL, vol. 153, 1983, pages 163 - 168, XP001313409
MINAMI H. ET AL.: "Functional analysis of norcoclaurine synthase in Coptis japonica", J. BIOL. CHEM., vol. 282, no. 9, 2 March 2007 (2007-03-02), pages 6274 - 6282, XP008126683 *
MINAMI H. ET AL.: "Microbial production of plant benzylisoquinoline alkaloids", PROC. NATL. ACAD. SCI. U.S.A., vol. 105, no. 21, 27 May 2008 (2008-05-27), pages 7393 - 7398, XP008126681 *
MINAMI, H. ET AL., JOURNAL OF BIOLOGICAL CHEMISTRY, 2007, pages 282 - 6274,6282
MINAMI, H.; DUBOUZET, E.; IWASA, K.; SATO, F.: "Functional analysis of norcoclaurine synthase in Coptis japonica", J. BIOL. CHEM., vol. 282, 2007, pages 6274 - 6282, XP008126683, DOI: doi:10.1074/jbc.M608933200
MORISHIGE, T. ET AL., JOURNAL OF BIOLOGICAL CHEMISTRY, vol. 275, 2000, pages 23398 - 23405
MORISHIGE, T.; CHOI, K.B.; SATO, F.: "In vivo bioconversion of tetrahydroisoquinoline by recombinant coclaurine N-methyltransferase", BIOSCI. BIOTECHNOL. BIOCHEM., vol. 68, 2004, pages 939 - 941
MORISHIGE, T.; TSUJITA, T.; YAMADA, Y.; SATO, F.: "Molecular characterization of the S-adenosyl-L-methionine:3'-hydroxy-N-methylcoclaurine 4'-O-methyltransferase involved in isoquinoline alkaloid biosynthesis in Coptis japonica", J. BIOL. CHEM., vol. 275, 2000, pages 23398 - 23405, XP002277118, DOI: doi:10.1074/jbc.M002439200
NUCLEIC ACIDS RES., vol. 10, 1982, pages 6487 - 6500
OEDA K; SAKAKI T; OHKAWA H: "Expression of rat liver cytochrome P-450MC cDNA in Saccharomyces cerevisiae", DNA, vol. 4, 1985, pages 203 - 210, XP000196032
PARK, S.U.; YU, M.; FACCHINI, P.J.: "Antisense RNA-mediated suppression of benzophenanthridine alkaloid biosynthesis in transgenic cell cultures of California poppy", PLANT PHYSIOL., vol. 128, 2002, pages 696 - 706, XP002317946, DOI: doi:10.1104/pp.128.2.696
PARK, S.U.; YU, M.; FACCHINI, P.J.: "Modulation of berberine bridge enzyme levels in transgenic root cultures of California poppy alters the accumulation of benzophenanthridine alkaloids", PLANT MOL. BIOL., vol. 51, 2003, pages 153 - 164, XP019262396, DOI: doi:10.1023/A:1021199311049
RATHBONE, D.A.; BRUCE, N.C.: "Microbial transformation of alkaloids", CURR. OPIN. MICROBIAL., vol. 5, 2002, pages 274 - 281
RO.D.K. ET AL.: "Production of the antimalarial drug precursor artemisinic acid in engineered yeast.", NATURE, vol. 440, 2006, pages 940 - 943
ROH J.H. ET AL.: "Purification, cloning, and three-dimensional structure prediction of Micrococcus luteus FAD-containing tyramine oxidase", BIOCHEM. BIOPHYS. RES. COMMUN., vol. 268, no. 2, 16 February 2000 (2000-02-16), pages 293 - 297, XP008126682 *
SAKAI T; AKIYOSHI-SHIBATA M; YABUSAKI Y; OHKAWA H: "Organella- targetted expression of rat liver cytochrome P450c27 in yeast", J BIOL CHEM, vol. 267, 1992, pages 16497 - 16502
SATO F.: "Daichokin ni Okeru Isoquinoline Alkaloid Seisan no Kokoromi", JOURNAL OF JAPAN FOUNDATION OF APPLIED ENZYMOLOGY, vol. 42, 1 February 2008 (2008-02-01), pages 79 - 80 *
SCHMIDT, J.; BOETTCHER, C.; KUHNT, C.; KUTCHAN, T.M.; ZENK, M.H.: "Poppy alkaloid profiling by electrospray tandem mass spectrometry and electrospray FT-ICR mass spectrometry after [ring-13C6]-tyramine feeding", PHYTOCHEMISTRY, vol. 68, 2007, pages 189 - 202, XP005822119, DOI: doi:10.1016/j.phytochem.2006.10.003
See also references of EP2169075A4 *

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US10240175B2 (en) 2006-10-19 2019-03-26 California Institute Of Technology Compositions and methods for producing benzylisoquinoline alkaloids
US20160304923A1 (en) 2006-10-19 2016-10-20 California Institute Of Technology Compositions and methods for producing benzylisoquinoline alkaloids
US10240176B2 (en) 2006-10-19 2019-03-26 California Institute Of Technology Compositions and methods for producing benzylisoquinoline alkaloids
JP5761723B2 (ja) * 2010-09-22 2015-08-12 石川県公立大学法人 植物ベンジルイソキノリンアルカロイドの生産方法
WO2012039438A1 (ja) * 2010-09-22 2012-03-29 石川県公立大学法人 植物ベンジルイソキノリンアルカロイドの生産方法
US20140134689A1 (en) * 2011-03-28 2014-05-15 The Regents Of The University Of California Host Cells and Methods for Oxidizing Aromatic Amino Acids
US10597685B2 (en) * 2011-03-28 2020-03-24 The Regents Of The University Of California Host cells and methods for oxidizing aromatic amino acids
US11214819B2 (en) 2013-03-15 2022-01-04 The Board Of Trustees Of The Leland Stanford Junior University Benzylisoquinoline alkaloids (BIA) producing microbes, and methods of making and using the same
US9534241B2 (en) 2013-03-15 2017-01-03 The Board Of Trustees Of The Leland Stanford Junior University Benzylisoquinoline alkaloids (BIA) producing microbes, and methods of making and using the same
US10017799B2 (en) 2013-03-15 2018-07-10 The Board Of Trustees Of The Leland Stanford Junior University Benzylisoquinoline alkaloids (BIA) producing microbes, and methods of making and using the same
US10858681B2 (en) 2013-03-15 2020-12-08 The Board Of Trustees Of The Leland Stanford Junior University Benzylisoquinoline alkaloids (BIA) producing microbes, and methods of making and using the same
US10988787B2 (en) 2013-03-15 2021-04-27 The Board Of Trustees Of The Leland Stanford Junior University Benzylisoquinoline alkaloids (BIA) producing microbes, and methods of making and using the same
US20160251688A1 (en) 2013-11-04 2016-09-01 The Board Of Trustees Of The Leland Stanford Junior University Benzylisoquinoline alkaloid (bia) precursor producing microbes, and methods of making and using the same
US12018304B2 (en) 2013-11-04 2024-06-25 The Board Of Trustees Of The Leland Stanford Junior University Benzylisoquinoline alkaloid (BIA) precursor producing microbes, and methods of making and using the same
US11124814B2 (en) 2013-11-04 2021-09-21 The Board Of Trustees Of The Leland Stanford Junior University Benzylisoquinoline alkaloid (BIA) precursor producing microbes, and methods of making and using the same
US10519453B2 (en) 2015-05-04 2019-12-31 The Board Of Trustees Of The Leland Stanford Junior University Benzylisoquinoline alkaloid (BIA) precursor producing microbes, and methods of making and using the same
US10752903B2 (en) 2015-05-04 2020-08-25 The Board Of Trustees Of The Leland Stanford Junior University Benzylisoquinoline alkaloid (BIA) precursor producing microbes, and methods of making and using the same
US11859225B2 (en) 2015-05-08 2024-01-02 The Board Of Trustees Of The Leland Stanford Junior University Methods of producing epimerases and benzylisoquinoline alkaloids
US11427827B2 (en) 2017-08-03 2022-08-30 Antheia, Inc. Engineered benzylisoquinoline alkaloid epimerases and methods of producing benzylisoquinoline alkaloids
US10544420B2 (en) 2017-08-03 2020-01-28 Antheia, Inc. Engineered benzylisoquinoline alkaloid epimerases and methods of producing benzylisoquinoline alkaloids
JPWO2020090940A1 (ja) * 2018-10-30 2021-09-30 国立大学法人神戸大学 ベンジルイソキノリンアルカロイド（ｂｉａ）産生用の組換え宿主細胞及びベンジルイソキノリンアルカロイド（ｂｉａ）の新規製造方法
WO2020090940A1 (ja) * 2018-10-30 2020-05-07 国立大学法人神戸大学 ベンジルイソキノリンアルカロイド（ｂｉａ）産生用の組換え宿主細胞及びベンジルイソキノリンアルカロイド（ｂｉａ）の新規製造方法
JP7497047B2 (ja) 2018-10-30 2024-06-10 国立大学法人東京農工大学 ベンジルイソキノリンアルカロイド（ｂｉａ）産生用の組換え宿主細胞及びベンジルイソキノリンアルカロイド（ｂｉａ）の新規製造方法
US12480131B2 (en) 2019-03-08 2025-11-25 The Board Of Trustees Of The Leland Stanford Junior University Tropane alkaloid (TA) producing non-plant host cells, and methods of making and using the same
US12497638B2 (en) 2023-10-23 2025-12-16 The Board Of Trustees Of The Leland Stanford Junior University Methods of producing epimerases and benzylisoquinoline alkaloids

Also Published As

Publication number Publication date
JP5177573B2 (ja) 2013-04-03
US8993280B2 (en) 2015-03-31
JPWO2008153094A1 (ja) 2010-08-26
EP2169075A4 (en) 2012-09-19
EP2169075B1 (en) 2016-09-14
EP2169075A1 (en) 2010-03-31
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