CA2982075A1 - A non-caloric sweetener - Google Patents
A non-caloric sweetener Download PDFInfo
- Publication number
- CA2982075A1 CA2982075A1 CA2982075A CA2982075A CA2982075A1 CA 2982075 A1 CA2982075 A1 CA 2982075A1 CA 2982075 A CA2982075 A CA 2982075A CA 2982075 A CA2982075 A CA 2982075A CA 2982075 A1 CA2982075 A1 CA 2982075A1
- Authority
- CA
- Canada
- Prior art keywords
- rebaudioside
- sucrose synthase
- glycosyltransferase
- product
- udp
- 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.)
- Pending
Links
- 235000013615 non-nutritive sweetener Nutrition 0.000 title claims description 31
- 229930188195 rebaudioside Natural products 0.000 claims abstract description 169
- 238000000034 method Methods 0.000 claims abstract description 130
- RPYRMTHVSUWHSV-CUZJHZIBSA-N rebaudioside D Chemical compound O([C@H]1[C@H](O)[C@@H](CO)O[C@H]([C@@H]1O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)O[C@]12C(=C)C[C@@]3(C1)CC[C@@H]1[C@@](C)(CCC[C@]1([C@@H]3CC2)C)C(=O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O RPYRMTHVSUWHSV-CUZJHZIBSA-N 0.000 claims abstract description 129
- 235000019202 steviosides Nutrition 0.000 claims abstract description 87
- 102000004190 Enzymes Human genes 0.000 claims abstract description 75
- 108090000790 Enzymes Proteins 0.000 claims abstract description 75
- RLLCWNUIHGPAJY-RYBZXKSASA-N Rebaudioside E Natural products O=C(O[C@H]1[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O2)[C@@H](O)[C@@H](O)[C@H](CO)O1)[C@]1(C)[C@@H]2[C@@](C)([C@@H]3[C@@]4(CC(=C)[C@@](O[C@@H]5[C@@H](O[C@@H]6[C@@H](O)[C@H](O)[C@@H](O)[C@H](CO)O6)[C@H](O)[C@@H](O)[C@H](CO)O5)(C4)CC3)CC2)CCC1 RLLCWNUIHGPAJY-RYBZXKSASA-N 0.000 claims abstract description 68
- RLLCWNUIHGPAJY-SFUUMPFESA-N rebaudioside E Chemical compound O([C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1O[C@]12C(=C)C[C@@]3(C1)CC[C@@H]1[C@@](C)(CCC[C@]1([C@@H]3CC2)C)C(=O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O RLLCWNUIHGPAJY-SFUUMPFESA-N 0.000 claims abstract description 68
- 230000004927 fusion Effects 0.000 claims abstract description 66
- 239000004383 Steviol glycoside Substances 0.000 claims abstract description 40
- 235000019411 steviol glycoside Nutrition 0.000 claims abstract description 40
- 229930182488 steviol glycoside Natural products 0.000 claims abstract description 40
- 150000008144 steviol glycosides Chemical class 0.000 claims abstract description 40
- 239000000047 product Substances 0.000 claims description 198
- DRTQHJPVMGBUCF-XVFCMESISA-N Uridine Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C=C1 DRTQHJPVMGBUCF-XVFCMESISA-N 0.000 claims description 160
- 108010043934 Sucrose synthase Proteins 0.000 claims description 100
- 108700023372 Glycosyltransferases Proteins 0.000 claims description 86
- 102000051366 Glycosyltransferases Human genes 0.000 claims description 86
- 235000013361 beverage Nutrition 0.000 claims description 82
- DRTQHJPVMGBUCF-PSQAKQOGSA-N beta-L-uridine Natural products O[C@H]1[C@@H](O)[C@H](CO)O[C@@H]1N1C(=O)NC(=O)C=C1 DRTQHJPVMGBUCF-PSQAKQOGSA-N 0.000 claims description 80
- DRTQHJPVMGBUCF-UHFFFAOYSA-N uracil arabinoside Natural products OC1C(O)C(CO)OC1N1C(=O)NC(=O)C=C1 DRTQHJPVMGBUCF-UHFFFAOYSA-N 0.000 claims description 80
- 229940045145 uridine Drugs 0.000 claims description 80
- 229930006000 Sucrose Natural products 0.000 claims description 68
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 claims description 68
- 239000005720 sucrose Substances 0.000 claims description 68
- 239000008103 glucose Substances 0.000 claims description 60
- 235000003599 food sweetener Nutrition 0.000 claims description 58
- 239000003765 sweetening agent Substances 0.000 claims description 58
- HELXLJCILKEWJH-NCGAPWICSA-N rebaudioside A Chemical compound O([C@H]1[C@H](O)[C@@H](CO)O[C@H]([C@@H]1O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)O[C@]12C(=C)C[C@@]3(C1)CC[C@@H]1[C@@](C)(CCC[C@]1([C@@H]3CC2)C)C(=O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O HELXLJCILKEWJH-NCGAPWICSA-N 0.000 claims description 54
- XCCTYIAWTASOJW-XVFCMESISA-N Uridine-5'-Diphosphate Chemical compound O[C@@H]1[C@H](O)[C@@H](COP(O)(=O)OP(O)(O)=O)O[C@H]1N1C(=O)NC(=O)C=C1 XCCTYIAWTASOJW-XVFCMESISA-N 0.000 claims description 48
- UEDUENGHJMELGK-HYDKPPNVSA-N Stevioside Chemical compound O([C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1O[C@]12C(=C)C[C@@]3(C1)CC[C@@H]1[C@@](C)(CCC[C@]1([C@@H]3CC2)C)C(=O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O UEDUENGHJMELGK-HYDKPPNVSA-N 0.000 claims description 47
- OHHNJQXIOPOJSC-UHFFFAOYSA-N stevioside Natural products CC1(CCCC2(C)C3(C)CCC4(CC3(CCC12C)CC4=C)OC5OC(CO)C(O)C(O)C5OC6OC(CO)C(O)C(O)C6O)C(=O)OC7OC(CO)C(O)C(O)C7O OHHNJQXIOPOJSC-UHFFFAOYSA-N 0.000 claims description 47
- 229940013618 stevioside Drugs 0.000 claims description 47
- 150000001413 amino acids Chemical group 0.000 claims description 44
- 239000011541 reaction mixture Substances 0.000 claims description 44
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- 239000001512 FEMA 4601 Substances 0.000 claims description 41
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 41
- HELXLJCILKEWJH-SEAGSNCFSA-N Rebaudioside A Natural products O=C(O[C@H]1[C@@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1)[C@@]1(C)[C@@H]2[C@](C)([C@H]3[C@@]4(CC(=C)[C@@](O[C@H]5[C@H](O[C@H]6[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O6)[C@@H](O[C@H]6[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O6)[C@H](O)[C@@H](CO)O5)(C4)CC3)CC2)CCC1 HELXLJCILKEWJH-SEAGSNCFSA-N 0.000 claims description 41
- HELXLJCILKEWJH-UHFFFAOYSA-N entered according to Sigma 01432 Natural products C1CC2C3(C)CCCC(C)(C(=O)OC4C(C(O)C(O)C(CO)O4)O)C3CCC2(C2)CC(=C)C21OC(C1OC2C(C(O)C(O)C(CO)O2)O)OC(CO)C(O)C1OC1OC(CO)C(O)C(O)C1O HELXLJCILKEWJH-UHFFFAOYSA-N 0.000 claims description 41
- 235000019203 rebaudioside A Nutrition 0.000 claims description 41
- 239000000203 mixture Substances 0.000 claims description 38
- -1 AceK Chemical compound 0.000 claims description 37
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 claims description 36
- 150000003839 salts Chemical class 0.000 claims description 33
- HSCJRCZFDFQWRP-JZMIEXBBSA-N UDP-alpha-D-glucose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1OP(O)(=O)OP(O)(=O)OC[C@@H]1[C@@H](O)[C@@H](O)[C@H](N2C(NC(=O)C=C2)=O)O1 HSCJRCZFDFQWRP-JZMIEXBBSA-N 0.000 claims description 30
- HSCJRCZFDFQWRP-UHFFFAOYSA-N Uridindiphosphoglukose Natural products OC1C(O)C(O)C(CO)OC1OP(O)(=O)OP(O)(=O)OCC1C(O)C(O)C(N2C(NC(=O)C=C2)=O)O1 HSCJRCZFDFQWRP-UHFFFAOYSA-N 0.000 claims description 30
- 239000004615 ingredient Substances 0.000 claims description 29
- 229940024606 amino acid Drugs 0.000 claims description 28
- 235000000346 sugar Nutrition 0.000 claims description 28
- 101000630755 Arabidopsis thaliana Sucrose synthase 1 Proteins 0.000 claims description 27
- 102000004169 proteins and genes Human genes 0.000 claims description 26
- 235000013305 food Nutrition 0.000 claims description 25
- 239000002773 nucleotide Substances 0.000 claims description 24
- 125000003729 nucleotide group Chemical group 0.000 claims description 24
- QSRAJVGDWKFOGU-WBXIDTKBSA-N rebaudioside c Chemical compound O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](O[C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)[C@H](O)[C@@H](CO)O[C@H]1O[C@]1(CC[C@H]2[C@@]3(C)[C@@H]([C@](CCC3)(C)C(=O)O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O3)O)CC3)C(=C)C[C@]23C1 QSRAJVGDWKFOGU-WBXIDTKBSA-N 0.000 claims description 24
- 239000000758 substrate Substances 0.000 claims description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 19
- 108010009534 Arabidopsis sucrose synthase-1 Proteins 0.000 claims description 18
- SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 claims description 18
- 230000002194 synthesizing effect Effects 0.000 claims description 18
- YWPVROCHNBYFTP-UHFFFAOYSA-N Rubusoside Natural products C1CC2C3(C)CCCC(C)(C(=O)OC4C(C(O)C(O)C(CO)O4)O)C3CCC2(C2)CC(=C)C21OC1OC(CO)C(O)C(O)C1O YWPVROCHNBYFTP-UHFFFAOYSA-N 0.000 claims description 17
- PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 claims description 17
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 claims description 17
- YWPVROCHNBYFTP-OSHKXICASA-N rubusoside Chemical compound O([C@]12C(=C)C[C@@]3(C1)CC[C@@H]1[C@@](C)(CCC[C@]1([C@@H]3CC2)C)C(=O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O YWPVROCHNBYFTP-OSHKXICASA-N 0.000 claims description 17
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- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 16
- CWBZAESOUBENAP-QVNVHUMTSA-N Naringin dihydrochalcone Chemical compound O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1O[C@H]1[C@H](OC=2C=C(O)C(C(=O)CCC=3C=CC(O)=CC=3)=C(O)C=2)O[C@H](CO)[C@@H](O)[C@@H]1O CWBZAESOUBENAP-QVNVHUMTSA-N 0.000 claims description 16
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- ITVGXXMINPYUHD-CUVHLRMHSA-N neohesperidin dihydrochalcone Chemical compound C1=C(O)C(OC)=CC=C1CCC(=O)C(C(=C1)O)=C(O)C=C1O[C@H]1[C@H](O[C@H]2[C@@H]([C@H](O)[C@@H](O)[C@H](C)O2)O)[C@@H](O)[C@H](O)[C@@H](CO)O1 ITVGXXMINPYUHD-CUVHLRMHSA-N 0.000 claims description 16
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- 239000008123 high-intensity sweetener Substances 0.000 claims description 15
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- 239000004386 Erythritol Substances 0.000 claims description 9
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Classifications
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- C—CHEMISTRY; METALLURGY
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- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/20—Carbocyclic rings
- C07H15/24—Condensed ring systems having three or more rings
- C07H15/256—Polyterpene radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/20—Carbocyclic rings
- C07H15/24—Condensed ring systems having three or more rings
-
- 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
-
- 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.)
-
- 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)
-
- 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
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- C12N9/1048—Glycosyltransferases (2.4)
- C12N9/1051—Hexosyltransferases (2.4.1)
- C12N9/1062—Sucrose synthase (2.4.1.13)
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12Y—ENZYMES
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- C12Y204/01—Hexosyltransferases (2.4.1)
- C12Y204/01013—Sucrose synthase (2.4.1.13)
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- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12Y—ENZYMES
- C12Y204/00—Glycosyltransferases (2.4)
- C12Y204/01—Hexosyltransferases (2.4.1)
- C12Y204/01017—Glucuronosyltransferase (2.4.1.17)
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K2319/00—Fusion polypeptide
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
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- Health & Medical Sciences (AREA)
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- Polymers & Plastics (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Nutrition Science (AREA)
- Food Science & Technology (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Seasonings (AREA)
- Enzymes And Modification Thereof (AREA)
- Saccharide Compounds (AREA)
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| US14/269,435 | 2014-05-05 | ||
| PCT/US2015/029163 WO2015171555A1 (en) | 2014-05-05 | 2015-05-05 | A non-caloric sweetener |
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| CA2982075A1 true CA2982075A1 (en) | 2015-11-12 |
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| EP (3) | EP3418288B1 (enExample) |
| JP (1) | JP6641357B2 (enExample) |
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| AU (1) | AU2015256232B2 (enExample) |
| BR (1) | BR112016025147B1 (enExample) |
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| DK (1) | DK3140314T3 (enExample) |
| ES (1) | ES2750373T3 (enExample) |
| HU (1) | HUE045937T2 (enExample) |
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| NZ (1) | NZ725866A (enExample) |
| WO (1) | WO2015171555A1 (enExample) |
| ZA (1) | ZA201607592B (enExample) |
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| US9752174B2 (en) | 2013-05-28 | 2017-09-05 | Purecircle Sdn Bhd | High-purity steviol glycosides |
| US9522929B2 (en) | 2014-05-05 | 2016-12-20 | Conagen Inc. | Non-caloric sweetener |
| CN113549664B (zh) | 2014-09-19 | 2025-10-28 | 谱赛科有限责任公司 | 高纯度甜菊醇糖苷 |
| EP3197469B1 (en) | 2014-09-26 | 2023-08-09 | PureCircle USA Inc. | Stevia composition, production method and uses |
| AU2015327940B2 (en) | 2014-10-03 | 2020-04-16 | Conagen Inc. | Non-caloric sweeteners and methods for synthesizing |
| WO2016100689A1 (en) | 2014-12-17 | 2016-06-23 | Cargill, Incorporated | Steviol glycoside compounds, compositions for oral ingestion or use, and method for enhancing steviol glycoside solubility |
| EP3718417B1 (en) | 2015-04-03 | 2025-09-03 | DSM IP Assets B.V. | Steviol glycosides |
| WO2016168413A1 (en) | 2015-04-14 | 2016-10-20 | Conagen Inc. | Production of non-caloric sweeteners using engineered whole-cell catalysts |
| US10494397B2 (en) * | 2016-07-15 | 2019-12-03 | Pepsico, Inc. | Rebaudioside analogs |
| BR112019007504B1 (pt) | 2016-10-14 | 2023-05-09 | Conagen Inc | Método de preparação de uma composição de glicosídeo de esteviol |
| AU2016427130B2 (en) | 2016-10-21 | 2022-08-18 | Pepsico, Inc. | Method for preparing rebaudioside N using enzymatic method |
| JP6842800B2 (ja) * | 2016-10-21 | 2021-03-17 | ペプシコ・インク | 酵素的方法を使用してレバウディオサイドｊを調製するための方法 |
| WO2018093196A1 (ko) * | 2016-11-17 | 2018-05-24 | 서울대학교산학협력단 | 변형 류코노스톡속 균주를 이용한 스테비오사이드 배당체의 합성 방법 및 이에 의하여 제조된 신규한 스테비오사이드 배당체 |
| KR101997597B1 (ko) * | 2016-11-17 | 2019-07-08 | 서울대학교산학협력단 | 변형 류코노스톡속 균주를 이용한 스테비오사이드 배당체의 합성 방법 및 이에 의하여 제조된 신규한 스테비오사이드 배당체 |
| IL321402A (en) | 2017-02-03 | 2025-08-01 | Tate & Lyle Solutions Usa Llc | Engineered glycosyltransferases and steviol glycoside glucosylation methods |
| JP7194111B2 (ja) | 2017-03-06 | 2022-12-21 | コナゲン インコーポレイテッド | ステビオール配糖体レバウジオシドｄ４のレバウジオシドｅからの生合成製造 |
| EP3644758A4 (en) | 2017-06-30 | 2021-03-31 | Conagen Inc. | Hydrolysis of steviol glycosides by beta-glucosidase |
| CN109423486B (zh) * | 2017-08-29 | 2022-02-25 | 中国科学院分子植物科学卓越创新中心 | 新型udp-糖基转移酶及其应用 |
| CN107446874B (zh) * | 2017-09-25 | 2020-07-28 | 四川盈嘉合生科技有限公司 | 重组大肠杆菌及其在合成莱鲍迪苷d中的用途 |
| CN111868252B (zh) * | 2018-03-12 | 2025-06-03 | 科纳根公司 | 甜菊糖苷莱苞迪苷j和莱苞迪苷n的生物合成生产 |
| CN109415747B (zh) * | 2018-05-25 | 2022-05-03 | 邦泰生物工程(深圳)有限公司 | 一种酶改质甜菊糖的制备方法和制备用酶及应用 |
| MX2021001260A (es) | 2018-07-30 | 2021-04-12 | Tate & Lyle Solutions Usa Llc | Glucosiltransferasas modificadas con ingenieria genetica y metodos de glucosilacion de glucosido de esteviol. |
| JP2022501309A (ja) * | 2018-09-29 | 2022-01-06 | フイルメニツヒ ソシエテ アノニムFirmenich Sa | テルペングリコシド誘導体およびその使用 |
| CN111344399B (zh) * | 2018-11-16 | 2023-03-03 | 邦泰生物工程(深圳)有限公司 | 一种udp-葡萄糖基转移酶突变体、其应用及其制备莱鲍迪苷d的方法 |
| BR112021011419A2 (pt) * | 2018-12-12 | 2021-09-08 | Conagen Inc. | Método de produção de rebaudiosídeo r6-2a e/ou r6-2b, r7-2, r6-1 e r6-4a e/ou r6-4b, rebaudiosídeo sintético e produto de consumo oral |
| CN109750072B (zh) * | 2019-01-31 | 2022-04-19 | 南京工业大学 | 一种酶法制备莱鲍迪苷e的方法 |
| JP7318989B2 (ja) * | 2019-03-29 | 2023-08-01 | コナゲン インコーポレイテッド | Ｕｄｐ－ラムノースの生合成生産 |
| CN110878288B (zh) * | 2019-12-09 | 2020-12-29 | 安徽农业大学 | 多肽、核酸及其在合成橙花叔醇糖苷上的应用 |
| CN111378630A (zh) * | 2020-04-09 | 2020-07-07 | 北京农学院 | 一种融合蛋白及其高效表达方法与应用 |
| CN114045273B (zh) * | 2021-11-15 | 2022-07-22 | 四川大学 | 糖基转移酶OsUGT91C1突变体及其应用 |
| CN118974246A (zh) * | 2021-12-24 | 2024-11-15 | 株式会社三养社 | 莱鲍迪苷的生产 |
| US12446605B2 (en) | 2022-03-23 | 2025-10-21 | Sweegen, Inc. | Sweeteners |
| CN115433702A (zh) * | 2022-08-23 | 2022-12-06 | 江南大学 | 一种利用糖基转移酶高效生物合成莱鲍迪苷d2的方法 |
| CN117070487B (zh) * | 2023-03-27 | 2024-12-24 | 浙江大学 | 茶树芦丁:尿苷二磷酸葡萄糖基转移酶基因及其应用 |
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| JPH04149191A (ja) * | 1990-10-09 | 1992-05-22 | Nakano Vinegar Co Ltd | ステビオサイド糖転移化合物及びその製造方法 |
| WO2002010210A2 (en) | 2001-08-28 | 2002-02-07 | Bayer Cropscience Ag | Polypeptides for identifying herbicidally active compounds |
| US20090183270A1 (en) | 2002-10-02 | 2009-07-16 | Adams Thomas R | Transgenic plants with enhanced agronomic traits |
| US20080148432A1 (en) | 2005-12-21 | 2008-06-19 | Mark Scott Abad | Transgenic plants with enhanced agronomic traits |
| US9107436B2 (en) | 2011-02-17 | 2015-08-18 | Purecircle Sdn Bhd | Glucosylated steviol glycoside as a flavor modifier |
| US8524785B2 (en) | 2009-09-04 | 2013-09-03 | International Flavors And Fragrances Inc. | Methods for using rebaudioside C as a flavor enhancer |
| SG178376A1 (en) | 2009-09-04 | 2012-03-29 | Redpoint Bio Corp | Sweetness enhancers including rebaudioside a or d |
| EP2533651A1 (en) * | 2010-02-08 | 2012-12-19 | The Coca-Cola Company | Solubility enhanced terpene glycoside(s) |
| US9795156B2 (en) | 2011-03-17 | 2017-10-24 | E.P.C (Beijing) Plant Pharmaceutical Technology Co., Ltd | Rebaudioside B and derivatives |
| JP6262653B2 (ja) | 2011-08-08 | 2018-01-17 | エヴォルヴァ エスアー．Ｅｖｏｌｖａ Ｓａ． | ステビオール配糖体の組換え生産 |
| EP2793615A4 (en) | 2011-12-20 | 2016-07-20 | Cargill Inc | MIXTURE WITH LOW MONATIN AND REBAUDIOSIDE A CONTENT |
| FR2984743B1 (fr) | 2011-12-23 | 2014-08-22 | Oreal | Utilisation cosmetique du steviol, d'un derive glycoside du steviol, ou un de leurs isomeres pour stimuler, restaurer ou reguler le metabolisme des cellules de la peau et des semi-muqueuses. |
| FR2984742A1 (fr) | 2011-12-23 | 2013-06-28 | Oreal | Utilisation de steviol, d'un derive glycoside du steviol, ou d'un de leurs isomeres, pour prevenir, reduire et/ou traiter une alteration du teint de la peau. |
| EA201400836A8 (ru) | 2012-01-23 | 2016-03-31 | ДСМ АйПи АССЕТС Б.В. | Получение дитерпена |
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