WO2024256472A3 - Preparation of terpenoid compounds - Google Patents

Preparation of terpenoid compounds Download PDF

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Publication number
WO2024256472A3
WO2024256472A3 PCT/EP2024/066253 EP2024066253W WO2024256472A3 WO 2024256472 A3 WO2024256472 A3 WO 2024256472A3 EP 2024066253 W EP2024066253 W EP 2024066253W WO 2024256472 A3 WO2024256472 A3 WO 2024256472A3
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WO
WIPO (PCT)
Prior art keywords
preparation
present
provides
terpenoid compounds
compound
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/EP2024/066253
Other languages
French (fr)
Other versions
WO2024256472A2 (en
Inventor
Michel Schalk
Christian Görner
Daniel SOLIS ESCALANTE
Anastasia ATHANASAKOGLOU
René Marcel de Jong
Andrew MUCHLINSKI
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.)
Firmenich SA
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Firmenich SA
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 Firmenich SA filed Critical Firmenich SA
Priority to CN202480051169.1A priority Critical patent/CN121693575A/en
Priority to EP24732929.5A priority patent/EP4724592A2/en
Publication of WO2024256472A2 publication Critical patent/WO2024256472A2/en
Publication of WO2024256472A3 publication Critical patent/WO2024256472A3/en
Priority to MX2025014401A priority patent/MX2025014401A/en
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
    • C12P17/02—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
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/92—Naphthofurans; Hydrogenated naphthofurans
    • 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
    • C12N9/0004—Oxidoreductases (1.)
    • C12N9/0006—Oxidoreductases (1.) acting on CH-OH groups as donors (1.1)
    • 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
    • C12N9/0004—Oxidoreductases (1.)
    • C12N9/0071—Oxidoreductases (1.) acting on paired donors with incorporation of molecular oxygen (1.14)
    • C12N9/0073—Oxidoreductases (1.) acting on paired donors with incorporation of molecular oxygen (1.14) with NADH or NADPH as one donor, and incorporation of one atom of oxygen 1.14.13
    • 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
    • C12N9/10—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
    • 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
    • C12N9/14—Hydrolases (3)
    • C12N9/16—Hydrolases (3) acting on ester bonds (3.1)
    • 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
    • C12N9/14—Hydrolases (3)
    • C12N9/16—Hydrolases (3) acting on ester bonds (3.1)
    • C12N9/18—Carboxylic ester hydrolases (3.1.1)
    • 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
    • C12N9/88—Lyases (4.)
    • 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
    • C12N9/90—Isomerases (5.)
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12Y—ENZYMES
    • C12Y101/00—Oxidoreductases acting on the CH-OH group of donors (1.1)
    • C12Y101/01—Oxidoreductases acting on the CH-OH group of donors (1.1) with NAD+ or NADP+ as acceptor (1.1.1)
    • C12Y101/01001—Alcohol dehydrogenase (1.1.1.1)
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12Y—ENZYMES
    • C12Y114/00—Oxidoreductases acting on paired donors, with incorporation or reduction of molecular oxygen (1.14)
    • C12Y114/13—Oxidoreductases acting on paired donors, with incorporation or reduction of molecular oxygen (1.14) with NADH or NADPH as one donor, and incorporation of one atom of oxygen (1.14.13)
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12Y—ENZYMES
    • C12Y301/00—Hydrolases acting on ester bonds (3.1)
    • C12Y301/03—Phosphoric monoester hydrolases (3.1.3)
    • C12Y301/03027—Phosphatidylglycerophosphatase (3.1.3.27)
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12Y—ENZYMES
    • C12Y402/00—Carbon-oxygen lyases (4.2)
    • C12Y402/01—Hydro-lyases (4.2.1)
    • C12Y402/01129—Squalene--hopanol cyclase (4.2.1.129)
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12Y—ENZYMES
    • C12Y402/00—Carbon-oxygen lyases (4.2)
    • C12Y402/01—Hydro-lyases (4.2.1)
    • C12Y402/01137—Sporulenol synthase (4.2.1.137)
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12Y—ENZYMES
    • C12Y504/00—Intramolecular transferases (5.4)
    • C12Y504/99—Intramolecular transferases (5.4) transferring other groups (5.4.99)
    • C12Y504/99017—Squalene--hopene cyclase (5.4.99.17)
    • 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
    • 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
    • C12R2001/645—Fungi ; Processes using fungi
    • 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
    • C12R2001/645—Fungi ; Processes using fungi
    • C12R2001/85—Saccharomyces
    • C12R2001/865—Saccharomyces cerevisiae
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12Y—ENZYMES
    • C12Y205/00—Transferases transferring alkyl or aryl groups, other than methyl groups (2.5)
    • C12Y205/01—Transferases transferring alkyl or aryl groups, other than methyl groups (2.5) transferring alkyl or aryl groups, other than methyl groups (2.5.1)
    • C12Y205/01029—Geranylgeranyl diphosphate synthase (2.5.1.29)
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12Y—ENZYMES
    • C12Y301/00—Hydrolases acting on ester bonds (3.1)
    • C12Y301/01—Carboxylic ester hydrolases (3.1.1)
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12Y—ENZYMES
    • C12Y401/00—Carbon-carbon lyases (4.1)
    • C12Y401/02—Aldehyde-lyases (4.1.2)

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Zoology (AREA)
  • Wood Science & Technology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Genetics & Genomics (AREA)
  • General Health & Medical Sciences (AREA)
  • General Engineering & Computer Science (AREA)
  • Biochemistry (AREA)
  • Microbiology (AREA)
  • Biotechnology (AREA)
  • Biomedical Technology (AREA)
  • Molecular Biology (AREA)
  • Medicinal Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Enzymes And Modification Thereof (AREA)
  • Micro-Organisms Or Cultivation Processes Thereof (AREA)
  • Peptides Or Proteins (AREA)

Abstract

The present invention provides a process for the preparation of a compound of formula (I). Included in this invention is an in vivo process for the preparation of compound of formula (I) in recombinant cells. The present invention also provides recombinant cells which may be used in said process. The present invention also provides polypeptides which can be used in the present invention. The present invention also provides further processes for the preparation of further compounds.
PCT/EP2024/066253 2023-06-12 2024-06-12 Preparation of terpenoid compounds Ceased WO2024256472A2 (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
CN202480051169.1A CN121693575A (en) 2023-06-12 2024-06-12 Preparation of terpenoid compounds
EP24732929.5A EP4724592A2 (en) 2023-06-12 2024-06-12 Preparation of terpenoid compounds
MX2025014401A MX2025014401A (en) 2023-06-12 2025-12-01 Preparation of terpenoid compounds

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP23178694.8 2023-06-12
EP23178694 2023-06-12

Publications (2)

Publication Number Publication Date
WO2024256472A2 WO2024256472A2 (en) 2024-12-19
WO2024256472A3 true WO2024256472A3 (en) 2025-04-03

Family

ID=86760502

Family Applications (2)

Application Number Title Priority Date Filing Date
PCT/EP2024/066253 Ceased WO2024256472A2 (en) 2023-06-12 2024-06-12 Preparation of terpenoid compounds
PCT/EP2024/066254 Ceased WO2024256473A2 (en) 2023-06-12 2024-06-12 Polypeptides for preparing terpenoid compounds

Family Applications After (1)

Application Number Title Priority Date Filing Date
PCT/EP2024/066254 Ceased WO2024256473A2 (en) 2023-06-12 2024-06-12 Polypeptides for preparing terpenoid compounds

Country Status (4)

Country Link
EP (2) EP4724593A2 (en)
CN (1) CN121693575A (en)
MX (2) MX2025014401A (en)
WO (2) WO2024256472A2 (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN119899828B (en) * 2025-01-17 2026-01-30 中国药科大学 Efficient production of novel drimane-type sesquiterpene compounds using SsDMS mutants

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010139719A2 (en) * 2009-06-05 2010-12-09 Basf Se Biocatalytic production of ambroxan
US20200385700A1 (en) * 2017-02-24 2020-12-10 International Flavors & Fragrances Inc. Squalene hopene cyclase and use thereof for producing ambroxan
WO2021005097A1 (en) * 2019-07-10 2021-01-14 Firmenich Sa Biocatalytic method for the controlled degradation of terpene compounds
WO2022003017A1 (en) * 2020-07-01 2022-01-06 Givaudan Sa Conversion of farnesylacetone to homofarnesylacetate by baeyer-villiger monooxygenase

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB201507207D0 (en) 2015-04-24 2015-06-10 Givaudan Sa Enzymes and applications thereof
MX386546B (en) 2016-12-22 2025-03-19 Firmenich & Cie Production of manool
MX2020012933A (en) 2018-07-10 2021-02-15 Firmenich & Cie Method for biocatalytic production of terpene compounds.
CN119137269A (en) * 2022-03-17 2024-12-13 奇华顿股份有限公司 SHC enzymes and enzyme variants

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010139719A2 (en) * 2009-06-05 2010-12-09 Basf Se Biocatalytic production of ambroxan
US20200385700A1 (en) * 2017-02-24 2020-12-10 International Flavors & Fragrances Inc. Squalene hopene cyclase and use thereof for producing ambroxan
WO2021005097A1 (en) * 2019-07-10 2021-01-14 Firmenich Sa Biocatalytic method for the controlled degradation of terpene compounds
WO2022003017A1 (en) * 2020-07-01 2022-01-06 Givaudan Sa Conversion of farnesylacetone to homofarnesylacetate by baeyer-villiger monooxygenase

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
ANDREAS SCHNEIDER ET AL: "Harnessing the Structure and Dynamics of the Squalene-Hopene Cyclase for (-)-Ambroxide Production", ANGEWANDTE CHEMIE INTERNATIONAL EDITION, VERLAG CHEMIE, HOBOKEN, USA, vol. 62, no. 22, E2023016, 18 April 2023 (2023-04-18), pages 1 - 10, XP072536251, ISSN: 1433-7851, DOI: 10.1002/ANIE.202301607 *
BENÍTEZ-MATEOS ANA I. ET AL: "Spheroplasts preparation boosts the catalytic potential of a squalene-hopene cyclase", NATURE COMMUNICATIONS, vol. 13, no. 1, 6269, 21 October 2022 (2022-10-21), UK, pages 1 - 9, XP093116646, ISSN: 2041-1723, Retrieved from the Internet <URL:https://www.nature.com/articles/s41467-022-34030-0> DOI: 10.1038/s41467-022-34030-0 *
SCHNEIDER A ET AL: "Supporting information for: Harnessing the Structure and Dynamics of the Squalene-Hopene Cyclase for (-)-Ambroxide Production", ANGEWANDTE CHEMIE INTERNATIONAL EDITION (ONLINE), 20 March 2023 (2023-03-20), pages i, 1 - 34, XP093249720, Retrieved from the Internet <URL:https://onlinelibrary.wiley.com/action/downloadSupplement?doi=10.1002%2Fanie.202301607&file=anie202301607-sup-0001-misc_information.pdf> *

Also Published As

Publication number Publication date
EP4724592A2 (en) 2026-04-15
MX2025014401A (en) 2026-01-07
EP4724593A2 (en) 2026-04-15
CN121693575A (en) 2026-03-17
MX2025014400A (en) 2026-01-07
WO2024256473A3 (en) 2025-03-27
WO2024256473A2 (en) 2024-12-19
WO2024256472A2 (en) 2024-12-19

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