JP6641357B2 - ノンカロリー甘味料 - Google Patents
ノンカロリー甘味料 Download PDFInfo
- Publication number
- JP6641357B2 JP6641357B2 JP2017511156A JP2017511156A JP6641357B2 JP 6641357 B2 JP6641357 B2 JP 6641357B2 JP 2017511156 A JP2017511156 A JP 2017511156A JP 2017511156 A JP2017511156 A JP 2017511156A JP 6641357 B2 JP6641357 B2 JP 6641357B2
- Authority
- JP
- Japan
- Prior art keywords
- rebaudioside
- ppm
- udp
- product
- beverage
- 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.)
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- 235000013615 non-nutritive sweetener Nutrition 0.000 title description 27
- 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 description 387
- DRTQHJPVMGBUCF-XVFCMESISA-N Uridine Chemical group 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
- 238000000034 method Methods 0.000 claims description 142
- 108010043934 Sucrose synthase Proteins 0.000 claims description 107
- 235000013361 beverage Nutrition 0.000 claims description 95
- 235000019202 steviosides Nutrition 0.000 claims description 92
- 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
- 102000004190 Enzymes Human genes 0.000 claims description 78
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- 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 description 73
- 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 description 73
- 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 71
- 229930006000 Sucrose Natural products 0.000 claims description 71
- 239000005720 sucrose Substances 0.000 claims description 71
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- 235000003599 food sweetener Nutrition 0.000 claims description 63
- 239000003765 sweetening agent Substances 0.000 claims description 63
- 239000008103 glucose Substances 0.000 claims description 61
- HELXLJCILKEWJH-NCGAPWICSA-N rebaudioside A Chemical group 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 53
- 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 52
- 229930188195 rebaudioside Natural products 0.000 claims description 52
- 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 49
- -1 Zurcoside A Chemical compound 0.000 claims description 49
- 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 49
- 229940013618 stevioside Drugs 0.000 claims description 49
- 108090000623 proteins and genes Proteins 0.000 claims description 45
- 150000003839 salts Chemical class 0.000 claims description 44
- 239000004383 Steviol glycoside Substances 0.000 claims description 43
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- 235000019411 steviol glycoside Nutrition 0.000 claims description 43
- 229930182488 steviol glycoside Natural products 0.000 claims description 43
- 150000008144 steviol glycosides Chemical class 0.000 claims description 42
- 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 40
- 239000011541 reaction mixture Substances 0.000 claims description 40
- 235000019203 rebaudioside A Nutrition 0.000 claims description 40
- 239000001512 FEMA 4601 Substances 0.000 claims description 39
- 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 39
- 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 38
- 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 37
- 239000000796 flavoring agent Substances 0.000 claims description 36
- 235000019634 flavors Nutrition 0.000 claims description 36
- 235000007164 Oryza sativa Nutrition 0.000 claims description 32
- 240000007594 Oryza sativa Species 0.000 claims description 30
- 235000000346 sugar Nutrition 0.000 claims description 30
- 102000004169 proteins and genes Human genes 0.000 claims description 29
- 239000002773 nucleotide Substances 0.000 claims description 25
- 125000003729 nucleotide group Chemical group 0.000 claims description 24
- 150000001413 amino acids Chemical group 0.000 claims description 22
- 229940024606 amino acid Drugs 0.000 claims description 21
- 239000000126 substance Substances 0.000 claims description 21
- 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 20
- 239000000758 substrate Substances 0.000 claims description 20
- 108010009534 Arabidopsis sucrose synthase-1 Proteins 0.000 claims description 19
- 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 19
- 239000002253 acid Substances 0.000 claims description 19
- PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 claims description 19
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 claims description 19
- 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 19
- 239000001329 FEMA 3811 Substances 0.000 claims description 18
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 18
- PBILBHLAPJTJOT-CQSZACIVSA-N Phyllodulcin Chemical compound C1=C(O)C(OC)=CC=C1[C@@H]1OC(=O)C2=C(O)C=CC=C2C1 PBILBHLAPJTJOT-CQSZACIVSA-N 0.000 claims description 18
- 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 18
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- 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 17
- 235000009566 rice Nutrition 0.000 claims description 17
- 230000002194 synthesizing effect Effects 0.000 claims description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 17
- 244000228451 Stevia rebaudiana Species 0.000 claims description 15
- 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 12
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- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
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- C07H15/24—Condensed ring systems having three or more rings
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- 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
- 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
- C07H15/256—Polyterpene radicals
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- 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.)
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- 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
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- C12N9/10—Transferases (2.)
- C12N9/1048—Glycosyltransferases (2.4)
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- 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)
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- 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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- 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
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- 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)
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- 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)
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- C07K—PEPTIDES
- C07K2319/00—Fusion polypeptide
Landscapes
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- Food Science & Technology (AREA)
- Polymers & Plastics (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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| WO2016049315A1 (en) | 2014-09-26 | 2016-03-31 | Purecircle Usa Inc. | Stevia composition, production method and uses |
| 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 |
| BR112017005656A2 (pt) | 2014-09-19 | 2018-07-31 | Purecircle Sdn Bhd | glicosídeos de esteviol de alta pureza |
| DK3201351T3 (da) | 2014-10-03 | 2021-02-22 | Conagen Inc | Kaloriefrie sødestoffer og fremgangsmåder til syntetisering |
| US10711024B2 (en) | 2014-12-17 | 2020-07-14 | Cargill, Incorporated | Steviol glycoside compounds, compositions for oral ingestion or use, and method for enhancing steviol glycoside solubility |
| WO2016156616A1 (en) | 2015-04-03 | 2016-10-06 | Dsm Ip Assets B.V. | Steviol glycosides |
| BR112017022019A2 (pt) | 2015-04-14 | 2018-07-31 | Conagen Inc. | produção de adoçantes não calóricos por meio da utilização de catalisadores de células inteiras modificadas |
| 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 |
| MX2019004630A (es) * | 2016-10-21 | 2019-07-15 | Pepsico Inc | Metodo para preparar rebaudiosido j usando el metodo enzimatico. |
| AU2016427130B2 (en) | 2016-10-21 | 2022-08-18 | Pepsico, Inc. | Method for preparing rebaudioside N using enzymatic method |
| KR101997597B1 (ko) * | 2016-11-17 | 2019-07-08 | 서울대학교산학협력단 | 변형 류코노스톡속 균주를 이용한 스테비오사이드 배당체의 합성 방법 및 이에 의하여 제조된 신규한 스테비오사이드 배당체 |
| WO2018093196A1 (ko) * | 2016-11-17 | 2018-05-24 | 서울대학교산학협력단 | 변형 류코노스톡속 균주를 이용한 스테비오사이드 배당체의 합성 방법 및 이에 의하여 제조된 신규한 스테비오사이드 배당체 |
| CN110914445B (zh) | 2017-02-03 | 2024-08-27 | 泰莱解决方案美国有限责任公司 | 工程化糖基转移酶和甜菊醇糖苷葡糖基化方法 |
| AU2017402700A1 (en) * | 2017-03-06 | 2019-10-17 | Conagen Inc. | Biosynthetic production of steviol glycoside rebaudioside D4 from rebaudioside E |
| AU2018294258A1 (en) | 2017-06-30 | 2020-02-06 | 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 |
| WO2019100676A1 (zh) * | 2018-05-25 | 2019-05-31 | 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 |
| JP7584401B2 (ja) | 2018-07-30 | 2024-11-15 | テイト アンド ライル ソリューションズ ユー・エス・エー エル・エル・シー | 操作されたグリコシルトランスフェラーゼおよびステビオールグリコシドのグルコシル化方法 |
| EP3781583A1 (en) * | 2018-09-29 | 2021-02-24 | Firmenich SA | Terpene glycoside derivatives and uses thereof |
| WO2020097922A1 (zh) * | 2018-11-16 | 2020-05-22 | 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 |
| CN113474464B (zh) * | 2018-12-12 | 2025-06-10 | 科纳根公司 | 变体甜菊醇糖苷的生物合成生产 |
| 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 |
| WO2020205685A1 (en) * | 2019-03-29 | 2020-10-08 | Conagen Inc. | Biosynthetic production of udp-rhamnose |
| 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 |
| JP2025500510A (ja) * | 2021-12-24 | 2025-01-09 | サムヤン コーポレイション | 糖転移酵素変異体、およびこれを利用したステビオール配糖体の製造方法 |
| 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 |
| MX2012002749A (es) | 2009-09-04 | 2012-07-04 | Redpoint Bio Corp | Aumentadores de dulzura incluyendo rebaudiosido a o d. |
| US8524785B2 (en) | 2009-09-04 | 2013-09-03 | International Flavors And Fragrances Inc. | Methods for using rebaudioside C as a flavor enhancer |
| AU2011213602B2 (en) * | 2010-02-08 | 2016-06-23 | 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 |
| SG10201606567TA (en) * | 2011-08-08 | 2016-10-28 | Evolva Sa | Recombinant production of steviol glycosides |
| 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. |
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