GB2587997B - A semisynthetic method of preparing neosaxitoxin - Google Patents

A semisynthetic method of preparing neosaxitoxin Download PDF

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Publication number
GB2587997B
GB2587997B GB2018189.7A GB202018189A GB2587997B GB 2587997 B GB2587997 B GB 2587997B GB 202018189 A GB202018189 A GB 202018189A GB 2587997 B GB2587997 B GB 2587997B
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United Kingdom
Prior art keywords
neosaxitoxin
preparing
semisynthetic method
semisynthetic
preparing neosaxitoxin
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GB2018189.7A
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GB202018189D0 (en
GB2587997A (en
Inventor
Ian Selwood Andrew
Van Ginkel Roelof
Alan Waugh Craig
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Cawthron Institute Trust Board
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Cawthron Institute Trust Board
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains three hetero rings
    • C07D487/14—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains three hetero rings
    • C07D487/20—Spiro-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains three hetero rings
    • C07D487/16—Peri-condensed systems
    • 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
    • C12N1/00—Microorganisms, e.g. protozoa; Compositions thereof; Processes of propagating, maintaining or preserving microorganisms or compositions thereof; Processes of preparing or isolating a composition containing a microorganism; Culture media therefor
    • C12N1/12—Unicellular algae; Culture media therefor
    • 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
    • C12N1/00—Microorganisms, e.g. protozoa; Compositions thereof; Processes of propagating, maintaining or preserving microorganisms or compositions thereof; Processes of preparing or isolating a composition containing a microorganism; Culture media therefor
    • C12N1/12—Unicellular algae; Culture media therefor
    • C12N1/125—Unicellular algae isolates
    • 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
    • C12P17/18—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms containing at least two hetero rings condensed among themselves or condensed with a common carbocyclic ring system, e.g. rifamycin
    • 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
    • C12P17/18—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms containing at least two hetero rings condensed among themselves or condensed with a common carbocyclic ring system, e.g. rifamycin
    • C12P17/182—Heterocyclic compounds containing nitrogen atoms as the only ring heteroatoms in the condensed system
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12M—APPARATUS FOR ENZYMOLOGY OR MICROBIOLOGY; APPARATUS FOR CULTURING MICROORGANISMS FOR PRODUCING BIOMASS, FOR GROWING CELLS OR FOR OBTAINING FERMENTATION OR METABOLIC PRODUCTS, i.e. BIOREACTORS OR FERMENTERS
    • C12M21/00—Bioreactors or fermenters specially adapted for specific uses
    • C12M21/02—Photobioreactors
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12M—APPARATUS FOR ENZYMOLOGY OR MICROBIOLOGY; APPARATUS FOR CULTURING MICROORGANISMS FOR PRODUCING BIOMASS, FOR GROWING CELLS OR FOR OBTAINING FERMENTATION OR METABOLIC PRODUCTS, i.e. BIOREACTORS OR FERMENTERS
    • C12M23/00—Constructional details, e.g. recesses, hinges
    • C12M23/02—Form or structure of the vessel
    • C12M23/14—Bags
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12M—APPARATUS FOR ENZYMOLOGY OR MICROBIOLOGY; APPARATUS FOR CULTURING MICROORGANISMS FOR PRODUCING BIOMASS, FOR GROWING CELLS OR FOR OBTAINING FERMENTATION OR METABOLIC PRODUCTS, i.e. BIOREACTORS OR FERMENTERS
    • C12M23/00—Constructional details, e.g. recesses, hinges
    • C12M23/22—Transparent or translucent parts
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12M—APPARATUS FOR ENZYMOLOGY OR MICROBIOLOGY; APPARATUS FOR CULTURING MICROORGANISMS FOR PRODUCING BIOMASS, FOR GROWING CELLS OR FOR OBTAINING FERMENTATION OR METABOLIC PRODUCTS, i.e. BIOREACTORS OR FERMENTERS
    • C12M29/00—Means for introduction, extraction or recirculation of materials, e.g. pumps
    • C12M29/06—Nozzles; Sprayers; Spargers; Diffusers
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12M—APPARATUS FOR ENZYMOLOGY OR MICROBIOLOGY; APPARATUS FOR CULTURING MICROORGANISMS FOR PRODUCING BIOMASS, FOR GROWING CELLS OR FOR OBTAINING FERMENTATION OR METABOLIC PRODUCTS, i.e. BIOREACTORS OR FERMENTERS
    • C12M41/00—Means for regulation, monitoring, measurement or control, e.g. flow regulation
    • C12M41/26—Means for regulation, monitoring, measurement or control, e.g. flow regulation of pH
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12M—APPARATUS FOR ENZYMOLOGY OR MICROBIOLOGY; APPARATUS FOR CULTURING MICROORGANISMS FOR PRODUCING BIOMASS, FOR GROWING CELLS OR FOR OBTAINING FERMENTATION OR METABOLIC PRODUCTS, i.e. BIOREACTORS OR FERMENTERS
    • C12M47/00—Means for after-treatment of the produced biomass or of the fermentation or metabolic products, e.g. storage of biomass
    • C12M47/02—Separating microorganisms from the culture medium; Concentration of biomass
    • 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
    • C12R2001/89—Algae ; Processes using algae

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biotechnology (AREA)
  • Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Genetics & Genomics (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Health & Medical Sciences (AREA)
  • Microbiology (AREA)
  • General Engineering & Computer Science (AREA)
  • Biochemistry (AREA)
  • Cell Biology (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Botany (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Virology (AREA)
  • Biomedical Technology (AREA)
  • Solid-Sorbent Or Filter-Aiding Compositions (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Polysaccharides And Polysaccharide Derivatives (AREA)
GB2018189.7A 2018-09-21 2018-09-21 A semisynthetic method of preparing neosaxitoxin Active GB2587997B (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/IB2018/057274 WO2020058750A1 (en) 2018-09-21 2018-09-21 A semisynthetic method of preparing neosaxitoxin

Publications (3)

Publication Number Publication Date
GB202018189D0 GB202018189D0 (en) 2021-01-06
GB2587997A GB2587997A (en) 2021-04-14
GB2587997B true GB2587997B (en) 2023-05-10

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GB2018189.7A Active GB2587997B (en) 2018-09-21 2018-09-21 A semisynthetic method of preparing neosaxitoxin

Country Status (8)

Country Link
US (2) US10822344B2 (en)
JP (1) JP7110403B2 (en)
CN (1) CN113166164B (en)
CA (1) CA3113727A1 (en)
CL (1) CL2020003015A1 (en)
GB (1) GB2587997B (en)
SG (1) SG11202102830SA (en)
WO (2) WO2020058750A1 (en)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA3113727A1 (en) * 2018-09-21 2020-03-26 The Cawthron Institute Trust Board A semisynthetic method of preparing neosaxitoxin
CN112461913B (en) * 2020-11-06 2022-02-22 华南农业大学 Method for improving identification capability of isomer compound
FR3130842A1 (en) * 2021-12-22 2023-06-23 CarbonWorks METHOD FOR CAPTURING PHYTOTOXINS IN A BIOLOGICAL REACTOR

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9249150B2 (en) * 2009-03-24 2016-02-02 Proteus S.A. Methods for purifying phycotoxins, pharmaceutical compositions containing purified phycotoxins, and methods of use thereof

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JP2003012699A (en) * 2001-07-04 2003-01-15 Japan Science & Technology Corp Method for manufacturing anti-paralytic shellfish poison antibody, new antibody, elisa measuring kit using the antibody, and system-labeling poison standard sample prepared by the manufacturing method
JP2006098293A (en) * 2004-09-30 2006-04-13 Japan Science & Technology Agency Method for transforming paralytic shellfish poisoning component
CL2009000723A1 (en) * 2009-03-24 2009-06-19 Proteus Sa Industrial purification method of biologically active phycotoxins comprising providing an adequate amount of a source of phycotoxins such as the cultivation of a cyanobacterial clone.
JP6422814B2 (en) * 2015-04-16 2018-11-14 学校法人北里研究所 Method for producing decarbamoyl saxitoxin and its analogs
CA3113727A1 (en) * 2018-09-21 2020-03-26 The Cawthron Institute Trust Board A semisynthetic method of preparing neosaxitoxin

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9249150B2 (en) * 2009-03-24 2016-02-02 Proteus S.A. Methods for purifying phycotoxins, pharmaceutical compositions containing purified phycotoxins, and methods of use thereof

Non-Patent Citations (12)

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Title
"CRM-NEO-c available from the National Research Council Canada", CRM-NEO-c is a certified calibration solution designed for use in chemical analysis methods, (20160122), URL: https://www.nrc-cnrc.gc.ca/eng/solutions/advisory/crm/list_product.html, (20181214) [X] 10 * as per the Wayback Machine see w *
CHO, Y. et al., "Column switching combined with hydrophilic interaction chromatography-tandem mass spectrometry for the analysis of saxitoxin analogues, and their biosynthetic intermediates in dinoflagellates", Journal of Chromatography A, (20160000), vol. 1474, doi:10.1016/j.chroma.2016.10.065, pag *
HWANG, D. F. et al., "Influence of environmental and nutritional factors on growth, toxicity, and toxin profile of dinoflagellate Alexandrium minutum", Toxicon, (20000000), vol. 38, pages 1491 - 1503 * see Materials and methods * *
LAYCOCK, M. V. et al., "Some in vitro chemical interconversions of paralytic shellfish poisoning (PSP) toxins useful in the preparation of analytical standards", Journal of Marine Biotechnology (Proceedings of the Third International Marine Biotechnology Conference, (19940000), vol. 3, no. 1-3, page *
LIM, P-T. et al., "Growth and toxin production of tropical Alexandrium minutum Halim (Dinophyceae) under various nitrogen to phosphorus ratios", Journal of Applied Phycology, (20100000), vol. 22, pages 203 - 210, * see Materials and Methods; Table 1; Figure la; p. 206 Toxins * *
MIROCHA, C. J. et al., Analysis of saxitoxin from urine using FAB/MS Midterm Report, 1919 University Avenue St. Paul , Minnesota 55105, (19900731),* see page 33 * *
PARKER, N. S. et al., "Growth of the toxic dinoflagellate Alexandrium minutum (Dinophyceae) using high biomass culture systems", Journal of Applied Phycology, (20020000), vol. 14, pages 313 - 324, * see p. 315 Growth in aerated tubes * *
PEAKE, R. W. A. et al., "Measurement of neosaxitoxin in human plasma using liquid- chromatography tandem mass spectrometry: Proof of concept for a pharmacokinetic application", Journal of Chromatography B, (20160000), vol. 1036 - 1, doi:10.1016/j.jchromb.2016.09.043, pages 42 - 49, see 2.1, 2.3 *
SAKAMOTO, S. et al., "Formation of intermediate conjugates in the reductive transformation of gonyautoxins to saxitoxins by thiol compounds", Fisheries Science, (20000000), vol. 66, pages 136 - 141 *
SATO, S. et al., "Identification of Thioether Intermediates in the Reductive Transformation of Gonyautoxins in Saxitoxins by Thiols", Bioinorganic & Medicinal Chemistry Letters, (20000000), vol. 10, doi:10.1016/S0960-894X(00)00332-2, pages 1787 - 1789 *
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Also Published As

Publication number Publication date
CN113166164A (en) 2021-07-23
CN113166164B (en) 2024-01-30
WO2020058949A1 (en) 2020-03-26
JP7110403B2 (en) 2022-08-01
GB202018189D0 (en) 2021-01-06
US20200407367A1 (en) 2020-12-31
US20200255441A1 (en) 2020-08-13
GB2587997A (en) 2021-04-14
US11028094B2 (en) 2021-06-08
WO2020058750A1 (en) 2020-03-26
CL2020003015A1 (en) 2021-06-25
SG11202102830SA (en) 2021-04-29
CA3113727A1 (en) 2020-03-26
JP2021526539A (en) 2021-10-07
US10822344B2 (en) 2020-11-03

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