CA2963300C - Methods and materials for biosynthesis of mogroside compounds - Google Patents

Methods and materials for biosynthesis of mogroside compounds Download PDF

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Publication number
CA2963300C
CA2963300C CA2963300A CA2963300A CA2963300C CA 2963300 C CA2963300 C CA 2963300C CA 2963300 A CA2963300 A CA 2963300A CA 2963300 A CA2963300 A CA 2963300A CA 2963300 C CA2963300 C CA 2963300C
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Prior art keywords
leu
mogroside
seq
polypeptide
glu
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CA2963300A
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English (en)
French (fr)
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CA2963300A1 (en
Inventor
Jens Houghton-Larsen
Katarzyna KRZYSTANEK
Angelika SEMMLER
Iver Klavs Riishede HANSEN
Soren DAMKIAER
Gary Liu
Yaoquan Liu
Jorgen Hansen
Sathish Kumar
Muthuswamy Panchapagesa MURALI
Nina Nicoline Rasmussen
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Evolva Holding SA
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Evolva AG
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Priority claimed from US14/504,109 external-priority patent/US10011859B2/en
Application filed by Evolva AG filed Critical Evolva AG
Priority to CA3232630A priority Critical patent/CA3232630A1/en
Publication of CA2963300A1 publication Critical patent/CA2963300A1/en
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Publication of CA2963300C publication Critical patent/CA2963300C/en
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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
    • C12P19/00—Preparation of compounds containing saccharide radicals
    • C12P19/18—Preparation of compounds containing saccharide radicals produced by the action of a glycosyl transferase, e.g. alpha-, beta- or gamma-cyclodextrins
    • 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
    • C12P33/00—Preparation of steroids
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/30—Artificial sweetening agents
    • A23L27/33—Artificial sweetening agents containing sugars or derivatives
    • A23L27/36—Terpene glycosides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H1/00—Processes for the preparation of sugar derivatives
    • C07H1/06—Separation; Purification
    • 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
    • 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)
    • C12N9/0014—Oxidoreductases (1.) acting on nitrogen containing compounds as donors (1.4, 1.5, 1.6, 1.7) acting on the CH-NH2 group of donors (1.4)
    • 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
    • C12N9/0004—Oxidoreductases (1.)
    • C12N9/0012—Oxidoreductases (1.) acting on nitrogen containing compounds as donors (1.4, 1.5, 1.6, 1.7)
    • C12N9/0036—Oxidoreductases (1.) acting on nitrogen containing compounds as donors (1.4, 1.5, 1.6, 1.7) acting on NADH or NADPH (1.6)
    • C12N9/0038—Oxidoreductases (1.) acting on nitrogen containing compounds as donors (1.4, 1.5, 1.6, 1.7) acting on NADH or NADPH (1.6) with a heme protein as acceptor (1.6.2)
    • C12N9/0042—NADPH-cytochrome P450 reductase (1.6.2.4)
    • 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
    • C12N9/0004—Oxidoreductases (1.)
    • C12N9/0071—Oxidoreductases (1.) acting on paired donors with incorporation of molecular oxygen (1.14)
    • 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.)
    • C12N9/0071—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.)
    • C12N9/1048—Glycosyltransferases (2.4)
    • C12N9/1051—Hexosyltransferases (2.4.1)
    • 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)
    • 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
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P19/00—Preparation of compounds containing saccharide radicals
    • C12P19/44—Preparation of O-glycosides, e.g. glucosides
    • C12P19/56—Preparation of O-glycosides, e.g. glucosides having an oxygen atom of the saccharide radical directly bound to a condensed ring system having three or more carbocyclic rings, e.g. daunomycin, adriamycin
    • H—ELECTRICITY
    • H04—ELECTRIC COMMUNICATION TECHNIQUE
    • H04J—MULTIPLEX COMMUNICATION
    • H04J14/00—Optical multiplex systems
    • H04J14/02—Wavelength-division multiplex systems
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Zoology (AREA)
  • Wood Science & Technology (AREA)
  • Genetics & Genomics (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Biotechnology (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • General Engineering & Computer Science (AREA)
  • Microbiology (AREA)
  • Molecular Biology (AREA)
  • Biomedical Technology (AREA)
  • Medicinal Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Physics & Mathematics (AREA)
  • Biophysics (AREA)
  • Plant Pathology (AREA)
  • Nutrition Science (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Computer Networks & Wireless Communication (AREA)
  • Signal Processing (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Micro-Organisms Or Cultivation Processes Thereof (AREA)
  • Enzymes And Modification Thereof (AREA)
  • Coloring Foods And Improving Nutritive Qualities (AREA)
CA2963300A 2014-10-01 2015-09-30 Methods and materials for biosynthesis of mogroside compounds Active CA2963300C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CA3232630A CA3232630A1 (en) 2014-10-01 2015-09-30 Methods and materials for biosynthesis of mogroside compounds

Applications Claiming Priority (13)

Application Number Priority Date Filing Date Title
US14/504,109 US10011859B2 (en) 2012-12-04 2014-10-01 Methods and materials for biosynthesis of mogroside compounds
US14/504,109 2014-10-01
US201462059136P 2014-10-02 2014-10-02
US62/059,136 2014-10-02
US201462087726P 2014-12-04 2014-12-04
US62/087,726 2014-12-04
US201462090836P 2014-12-11 2014-12-11
US62/090,836 2014-12-11
US201462091895P 2014-12-15 2014-12-15
US62/091,895 2014-12-15
US201562199115P 2015-07-30 2015-07-30
US62/199,115 2015-07-30
PCT/EP2015/072645 WO2016050890A2 (en) 2014-10-01 2015-09-30 Methods and materials for biosynthesis of mogroside compounds

Related Child Applications (1)

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CA3232630A Division CA3232630A1 (en) 2014-10-01 2015-09-30 Methods and materials for biosynthesis of mogroside compounds

Publications (2)

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CA2963300A1 CA2963300A1 (en) 2016-04-07
CA2963300C true CA2963300C (en) 2024-04-30

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CA2963300A Active CA2963300C (en) 2014-10-01 2015-09-30 Methods and materials for biosynthesis of mogroside compounds
CA3232630A Pending CA3232630A1 (en) 2014-10-01 2015-09-30 Methods and materials for biosynthesis of mogroside compounds

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US (2) US10633685B2 (https=)
EP (1) EP3201315A2 (https=)
JP (1) JP2017529860A (https=)
CN (1) CN107466320B (https=)
AU (2) AU2015326892B2 (https=)
CA (2) CA2963300C (https=)
IL (2) IL251380B (https=)
SG (2) SG10201902813XA (https=)
WO (1) WO2016050890A2 (https=)

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CN109439676A (zh) * 2018-09-26 2019-03-08 怀化兴科创生物技术有限公司 罗汉果环氧化物水解酶Sgeph5基因的应用
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CN110357936B (zh) * 2019-07-16 2020-10-16 湖南华诚生物资源股份有限公司 半合成罗汉果甜苷v的方法
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CN113388590B (zh) * 2021-06-07 2022-02-25 山西农业大学 一种细胞色素P450s的突变体
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CN114854722B (zh) * 2022-05-11 2024-01-09 成都普睿法药物研发有限公司 一种季也蒙念珠菌外切β-1,3-葡聚糖酶及其突变体及应用
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CN115896136B (zh) * 2022-12-22 2025-12-16 云南农业大学 与葫芦二烯醇羟化相关的细胞色素p450基因及其编码产物
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EP3201315A2 (en) 2017-08-09
US11091787B2 (en) 2021-08-17
AU2015326892A1 (en) 2017-03-30
CN107466320B (zh) 2021-11-05
IL251380B (en) 2020-09-30
US10633685B2 (en) 2020-04-28
CA2963300A1 (en) 2016-04-07
JP2017529860A (ja) 2017-10-12
AU2022204012B2 (en) 2024-06-27
IL276781A (en) 2020-10-29
CN107466320A (zh) 2017-12-12
SG10201902813XA (en) 2019-04-29
AU2022204012C1 (en) 2024-09-05
SG11201702123SA (en) 2017-04-27
WO2016050890A3 (en) 2016-06-30
US20170247735A1 (en) 2017-08-31
US20200325517A1 (en) 2020-10-15
WO2016050890A2 (en) 2016-04-07
AU2015326892B2 (en) 2022-03-10
AU2015326892A2 (en) 2017-05-25
CA3232630A1 (en) 2016-04-07
AU2022204012A1 (en) 2022-06-30
IL251380A0 (en) 2017-05-29

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