WO2022157180A1 - Plate-forme de synthèse in-vitro pour la génération d'isoprénoïdes - Google Patents

Plate-forme de synthèse in-vitro pour la génération d'isoprénoïdes Download PDF

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WO2022157180A1
WO2022157180A1 PCT/EP2022/051100 EP2022051100W WO2022157180A1 WO 2022157180 A1 WO2022157180 A1 WO 2022157180A1 EP 2022051100 W EP2022051100 W EP 2022051100W WO 2022157180 A1 WO2022157180 A1 WO 2022157180A1
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kinase
diphosphate
process according
seq
hemiterpene
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PCT/EP2022/051100
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Michael DIRKMANN
Andreas Vogel
Hanna DUDEK
Sebastian Bartsch
Lena SCHILLING
Rico Czaja
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C-Lecta Gmbh
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Priority to EP22700507.1A priority Critical patent/EP4281570A1/fr
Publication of WO2022157180A1 publication Critical patent/WO2022157180A1/fr

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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
    • C12P5/00—Preparation of hydrocarbons or halogenated hydrocarbons
    • C12P5/007—Preparation of hydrocarbons or halogenated hydrocarbons containing one or more isoprene units, i.e. terpenes
    • C—CHEMISTRY; METALLURGY
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    • C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
    • C12N9/0004—Oxidoreductases (1.)
    • C12N9/0071—Oxidoreductases (1.) acting on paired donors with incorporation of molecular oxygen (1.14)
    • C—CHEMISTRY; METALLURGY
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    • C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
    • C12N9/10—Transferases (2.)
    • C12N9/1085—Transferases (2.) transferring alkyl or aryl groups other than methyl groups (2.5)
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
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    • C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
    • C12N9/10—Transferases (2.)
    • C12N9/12—Transferases (2.) transferring phosphorus containing groups, e.g. kinases (2.7)
    • C12N9/1205—Phosphotransferases with an alcohol group as acceptor (2.7.1), e.g. protein kinases
    • C—CHEMISTRY; METALLURGY
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    • C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
    • C12N9/10—Transferases (2.)
    • C12N9/12—Transferases (2.) transferring phosphorus containing groups, e.g. kinases (2.7)
    • C12N9/1217—Phosphotransferases with a carboxyl group as acceptor (2.7.2)
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
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    • C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
    • C12N9/10—Transferases (2.)
    • C12N9/12—Transferases (2.) transferring phosphorus containing groups, e.g. kinases (2.7)
    • C12N9/1229—Phosphotransferases with a phosphate group as acceptor (2.7.4)
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
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    • C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
    • C12N9/90—Isomerases (5.)
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    • C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
    • C12P17/02—Oxygen as only ring hetero atoms
    • C12P17/04—Oxygen as only ring hetero atoms containing a five-membered hetero ring, e.g. griseofulvin, vitamin C
    • 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
    • C12P7/02—Preparation of oxygen-containing organic compounds containing a hydroxy group
    • 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
    • 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
    • C12P7/40—Preparation of oxygen-containing organic compounds containing a carboxyl group including Peroxycarboxylic acids
    • 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
    • C12P9/00—Preparation of organic compounds containing a metal or atom other than H, N, C, O, S or halogen
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12R—INDEXING SCHEME ASSOCIATED WITH SUBCLASSES C12C - C12Q, RELATING TO MICROORGANISMS
    • C12R2001/00—Microorganisms ; Processes using microorganisms
    • C12R2001/01—Bacteria or Actinomycetales ; using bacteria or Actinomycetales
    • C12R2001/185—Escherichia
    • C12R2001/19—Escherichia coli
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12R—INDEXING SCHEME ASSOCIATED WITH SUBCLASSES C12C - C12Q, RELATING TO MICROORGANISMS
    • C12R2001/00—Microorganisms ; Processes using microorganisms
    • C12R2001/90—Protozoa ; Processes using protozoa

Definitions

  • terpenoids are largely derived from two major diphosphorylated building blocks: isopentenyl pyrophosphate (IPP) and dimethylallyl pyrophosphate (DMAPP). Following their generation, such diphosphorylated building blocks may be subjected to sequential condensation under catalysis of specific prenyltransferases thereby resulting in geranyl pyrophosphate (GPP), famesyl pyrophosphate (FPP) and geranylgeranyl pyrophosphate (GGPP) which then may be converted to the more complex terpenoids under catalysis of appropriate terpene synthases. The resulting terpenoids may be then further functionalized either chemically or under enzymatic catalysis.
  • IPP isopentenyl pyrophosphate
  • DMAPP dimethylallyl pyrophosphate
  • the first phosphate donor is a triphosphorylated conjugate of a ribose or a deoxyribose with a nucleobase selected from the group consisting of adenine, guanine, inosine, cytosine, thymine, and uracil and even more preferably of adenosine.
  • the first phosphate donor is adenosine triphosphate (ATP).
  • ATP adenosine triphosphate
  • the second kinase is a isopentenyl phosphate kinase from Methanol- obus tindarius.
  • the second kinase according to the invention comprises such an amino acid sequence with a defined identity to the amino acid sequence of the first kinase, SEQ ID NO:3 or SEQ ID NO:4.
  • the second kinase according to the invention may comprise said amino acid sequence as a subsequence of its overall amino acid sequence, or that the second kinase according to the invention may essentially consist of said amino acid sequence.
  • said overall amino acid sequence may be extended, i.e. may comprise additional amino acid residues, at the N-ter- minus and/or at the C-terminus of said subsequence.
  • Such extension may be advantageous, for example, when the second kinase is to be immobilized on a solid support, e.g. for purification purposes.
  • the second kinase is an enzyme comprising a primary sequence having an identity of at least 60%, or at least 61%, or at least 62%, or at least 63%, or at least 64%; preferably at least 65%, or at least 66%, or at least 67%, or at least 68%, or at least 69%; more preferably at least 70%, or at least 71%, or at least 72%, or at least 73%, or at least 74%; still more preferably at least 75%, or at least 76%, or at least 77%, or at least 78%, or at least 79%; yet more preferably at least 80%, or at least 81%, or at least 82%, or at least 83%, or at least 84%; even more preferably at least 85%, or at least 86%, or at least 87%, or at least 88%, or at least 89%; most preferably at least 90%, or at least 91%, or at least 92%, or at least 93%, or at least 94%; and in particular at least 95%, or at least 96%,
  • the monoterpene diphosphate is geranyl pyrophosphate (GPP); and/or
  • the first hemiterpene diphosphate is isopentenyl pyrophosphate (IPP); and/or
  • the process is characterized in that:
  • the second hemiterpene alcohol is a constitutional isomer of the first hemiterpene alcohol.
  • the third phosphate donor has the same molecular structure as the first and /or second phosphate donor.
  • the fourth phosphate donor is selected from the group consisting of organic and/or inorganic mono- or polyphosphates; preferably wherein the first phosphate donor is a nucleoside mono- or polyphosphate, phosphoenolpyruvic acid, acetyl phosphate, phosphoenolpyruvate, glucose-6-phos- phate, fructose- 1,6-bisphosphate, 3 -phosphoglycerate.
  • the fourth phosphate donor has the same molecular structure as the first and second and/or third phosphate donor.
  • the molar ratio of the first hemiterpene alcohol relative to second hemiterpene alcohol is at least 1: 10, or at least 1:2, or preferably at least 1: 1, or most preferably at least 2: 1 or 3: 1.
  • step (as) comprises the substep of
  • the isomerase is an enzyme comprising a primary sequence having an identity of at least 60%, or at least 61%, or at least 62%, or at least 63%, or at least 64%; preferably at least 65%, or at least 66%, or at least 67%, or at least 68%, or at least 69%; more preferably at least 70%, or at least 71%, or at least 72%, or at least 73%, or at least 74%; still more preferably at least 75%, or at least 76%, or at least 77%, or at least 78%, or at least 79%; yet more preferably at least 80%, or at least 81%, or at least 82%, or at least 83%, or at least 84%; even more preferably at least 85%, or at least 86%, or at least 87%, or at least 88%, or at least 89%; most preferably at least 90%, or at least 91%, or at least 92%, or at least 93%, or at least 94%; and in particular at least 95%, or at least 90%, or at least 9
  • the second hemiterpene diphosphate is dimethylallyl pyrophosphate (DMAPP).
  • steps (gi) or (g 2 ) are repeated at least once; and/or at least one of steps (gi) or (g 2 ) is performed in a single reactor; and/or steps (gi) or (g 2 ) are performed simultaneously.
  • step (j) reacting the sesquiterpene obtained in step (i) under catalysis of a monooxygenase (EC 1. 14.x.x) thereby obtaining sesquiterpenoid.
  • step (m) reacting phytoene obtained in step (e) under catalysis of one or more enzyme selected from the group consisting of phytoene desaturase (EC 1.3.99.31), ⁇ -carotene desaturase (EC 1.3.99.26), lycopene-a-cyclase (EC 5.5.1.18), lycopene [3-cyclase (EC 5.5.1.19) thereby obtaining the tetraterpenoid.
  • one or more enzyme selected from the group consisting of phytoene desaturase (EC 1.3.99.31), ⁇ -carotene desaturase (EC 1.3.99.26), lycopene-a-cyclase (EC 5.5.1.18), lycopene [3-cyclase (EC 5.5.1.19) thereby obtaining the tetraterpenoid.
  • the composition further comprises a (i) sesquiterpene obtainable by the process according to the invention as described above in combination with a (ii) sesquiterpene synthase.
  • Clause 7 The process according to any of the preceding clauses, preferably according to any of clauses 1 to 3 or 6 wherein the first kinase is an enzyme comprising a primary sequence having an identity of at least 60%, or at least 61%, or at least 62%, or at least 63%, or at least 64%; preferably at least 65%, or at least 66%, or at least 67%, or at least 68%, or at least 69%; more preferably at least 70%, or at least 71%, or at least 72%, or at least 73%, or at least 74%; still more preferably at least 75%, or at least 76%, or at least 77%, or at least 78%, or at least 79%; yet more preferably at least 80%, or at least 81%, or at least 82%, or at least 83%, or at least 84%; even more preferably at least 85%, or at least 86%, or at least 87%, or at least 88%, or at least 89%; most preferably at least 90%, or at least 91%, or at
  • the first hemiterpene alcohol is isoprenol
  • the first hemiterpene diphosphate is isopentenyl pyrophosphate (IPP); and/or
  • Clause 80 The process according to any of the preceding clauses, preferably according to clause 79, wherein the second hemiterpene alcohol is selected from the group consisting of isoprenol, 3-methyl-3- buten-2-ol, tiglic alcohol, angelicic alcohol, senecioic alcohol and isovaleric alcohol, 2-Methyl-2 -propen- l-ol, 3 -methylene- 1 -pentanol, 2-hexen-l-ol, 4-penten-l-ol, 3 -thiopheneethanol, 4-methyl-4-pen- ten-l-ol, 2-(Z)-hexen-l-ol, 2-butyn-l-ol, 3 -furanmethanol, 3-buten-l-ol, (2E)-buten-l-ol, 3 -methyl -2- penten-l-ol, 3-butyn-l-ol, 3,4-dimethyl-(2E)-penten-l
  • Clause 83 The process according to any of the preceding clauses, preferably according to any of clauses 79 to 82, wherein the second hemiterpene alcohol is prenol.
  • Clause 105 The process according to any of the preceding clauses, preferably according to any of clauses 95 to 98, wherein the isomerase is an enzyme comprising a primary sequence having an identity of at least 60%, or at least 61%, or at least 62%, or at least 63%, or at least 64%; preferably at least 65%, or at least 66%, or at least 67%, or at least 68%, or at least 69%; more preferably at least 70%, or at least 71%, or at least 72%, or at least 73%, or at least 74%; still more preferably at least 75%, or at least 76%, or at least 77%, or at least 78%, or at least 79%; yet more preferably at least 80%, or at least 81%, or at least 82%, or at least 83%, or at least 84%; even more preferably at least 85%, or at least 86%, or at least 87%, or at least 88%, or at least 89%; most preferably at least 90%, or at least 91%, or at least 9
  • Clause 123 A process for the synthesis of a cannanbinoide comprising the process according to any of the preceding clauses, preferably comprising the process for the synthesis of a monoterpene diphosphate according to any clauses 41 to 47 or any of clauses 78 to 114.
  • Clause 132 The process according to any of the preceding clauses, preferably according to clause 131 additionally comprising the steps of:
  • Clause 135 The process according to any of the preceding clauses, preferably according to clause 134 additionally comprising the steps of:
  • Clause 138 The process according to any of the preceding clauses, preferably according to clause 137 additionally comprising the step of:
  • Clause 149 The process according to any of the preceding clauses, preferably according to any of clauses 146 to 148, wherein the fifth kinase is an acetate kinase belonging to EC 2.7.2. 1 or EC 2.7.4.1.
  • Clause 177 The composition according to any of clauses 166 to 176 further comprising a (i) tetraterpene obtainable by the process according to any of the preceding clauses, preferably according to any of clauses 73 to 78 or any of clauses 79 to 115 in combination with a (ii) tetraterpene synthase.
  • EXAMPLE 11 General synthesis of sesquiterpenes starting from IOH and POH under employment of a acetyl phosphate -based ATP-regeneration system

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  • Wood Science & Technology (AREA)
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  • Bioinformatics & Cheminformatics (AREA)
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  • General Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Biotechnology (AREA)
  • Molecular Biology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Biomedical Technology (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)

Abstract

L'invention concerne un procédé de production d'isoprénoïdes par une plate-forme de synthèse in vitro impliquant au moins les étapes de phosphorylation d'un premier alcool hémiterpénique avec un premier donneur de phosphate sous la catalyse d'une première kinase, obtenant ainsi un premier hémiterpène monophosphate, et de phosphorylation de ce dernier avec un second donneur de phosphate sous la catalyse d'une seconde kinase, obtenant ainsi au moins un premier hémiterpène diphosphate. L'invention concerne en outre une composition comprenant un premier hémiterpène diphosphate pouvant être obtenu par le procédé selon l'invention.
PCT/EP2022/051100 2021-01-20 2022-01-19 Plate-forme de synthèse in-vitro pour la génération d'isoprénoïdes WO2022157180A1 (fr)

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Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011009132A2 (fr) 2009-07-17 2011-01-20 The Salk Institute For Biological Studies Procédés et composition pour la synthèse du diphosphate d’isoprénoïde
WO2011123567A1 (fr) * 2010-03-31 2011-10-06 Codexis, Inc. Production de diphosphate de géranyle
WO2019023192A1 (fr) 2017-07-24 2019-01-31 Spogen Biotech Inc. Enzymes de détoxification d'herbicides et leurs utilisations
WO2019232025A2 (fr) 2018-05-29 2019-12-05 Massachusetts Institute Of Technology Production technologique de microbes pour produire des isoprénoïdes
WO2020150340A1 (fr) 2019-01-15 2020-07-23 North Carolina State University Isoprénoïdes et leurs procédés de fabrication
WO2021134024A1 (fr) * 2019-12-26 2021-07-01 The Regents Of The University Of California Plate-forme de biosynthèse pour la production de cannabinoïdes et d'autres composés prénylés

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Publication number Priority date Publication date Assignee Title
WO2011009132A2 (fr) 2009-07-17 2011-01-20 The Salk Institute For Biological Studies Procédés et composition pour la synthèse du diphosphate d’isoprénoïde
WO2011123567A1 (fr) * 2010-03-31 2011-10-06 Codexis, Inc. Production de diphosphate de géranyle
WO2019023192A1 (fr) 2017-07-24 2019-01-31 Spogen Biotech Inc. Enzymes de détoxification d'herbicides et leurs utilisations
WO2019232025A2 (fr) 2018-05-29 2019-12-05 Massachusetts Institute Of Technology Production technologique de microbes pour produire des isoprénoïdes
WO2020150340A1 (fr) 2019-01-15 2020-07-23 North Carolina State University Isoprénoïdes et leurs procédés de fabrication
WO2021134024A1 (fr) * 2019-12-26 2021-07-01 The Regents Of The University Of California Plate-forme de biosynthèse pour la production de cannabinoïdes et d'autres composés prénylés

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DATABASE UniProt [online] 2 December 2020 (2020-12-02), COPELAND, A. ET AL.: "Isopentenyl phosphate kinase, EC=2.7.4.26", XP055921613, retrieved from https://www.uniprot.org/uniprot/A7NR95.txt?version=71 Database accession no. A7NR95 *
DATABASE UniProt [online] 2 December 2020 (2020-12-02), KOYAMA, T. ET AL.: "Full=Farnesyl diphosphate synthase, Short=FPP synthase, EC=2.5.1.10, Full=(2E,6E)-farnesyl diphosphate synthase, Full=Geranyltranstransferase", XP055923227, retrieved from https://www.uniprot.org/uniprot/Q08291.txt?version=86 Database accession no. Q08291 *
DATABASE UniProt [online] 2 December 2020 (2020-12-02), RASKO, D.A. ET AL: "Full=Hydroxyethylthiazole kinase, DE EC=2.7.1.50, Full=4-methyl-5-beta-hydroxyethylthiazole kinase, DE Short=TH kinase, DE Short=Thz kinase", XP055923085, retrieved from https://www.uniprot.org/uniprot/A8A1W9.txt?version=69 Database accession no. A8A1W9 *
DATABASE UniProt [online] 2 December 2020 (2020-12-02), TAKAMI, H. ET AL.: "Full=Acetate kinase, EC=2.7.2.1", XP055821208, retrieved from https://www.uniprot.org/uniprot/Q5KW66.txt?version=87 Database accession no. Q5KW66 *
DATABASE UniProt [online] 20 December 2020 (2020-12-20), WOOD, V. ET AL.: "Full=Isopentenyl-diphosphate Delta-isomerase, EC=5.3.3.2, Full=Isopentenyl pyrophosphate isomerase, Short=IPP isomerase", XP055923317, Database accession no. Q10132 *
DATABASE UniProt [online] 7 October 2020 (2020-10-07), EISEN, J. ET AL.: "Full=Isopentenyl phosphate kinase, Short=IPK, EC=2.7.4.26", XP055922874, retrieved from https://www.uniprot.org/uniprot/W9DTD1.txt?version=29 Database accession no. W9DTD1 *
DATABASE UniProt [online] 7 October 2020 (2020-10-07), VERDOES, J.C. & OOYEN, A.J.J.: "Full=Isopentenyl-diphosphate Delta-isomerase, EC=5.3.3.2, Full=Isopentenyl pyrophosphate isomerase, Short=IPP isomerase", XP055923318, Database accession no. O42641 *
F. WILLIAM STUDIER, PROTEIN EXPRESSION AND PURIFICATION, vol. 41, 2005, pages 207 - 234
IACAZIO, ACS OMEGA, vol. 4, no. 4, 2019, pages 7838 - 7849
WILLIAMS, ACS SYNTH. BIOL., vol. 8, no. 2, 2019, pages 232 - 238

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