RU2736155C1 - Способ получения ребаудиозида c с применением ферментативного способа - Google Patents
Способ получения ребаудиозида c с применением ферментативного способа Download PDFInfo
- Publication number
- RU2736155C1 RU2736155C1 RU2019113355A RU2019113355A RU2736155C1 RU 2736155 C1 RU2736155 C1 RU 2736155C1 RU 2019113355 A RU2019113355 A RU 2019113355A RU 2019113355 A RU2019113355 A RU 2019113355A RU 2736155 C1 RU2736155 C1 RU 2736155C1
- Authority
- RU
- Russia
- Prior art keywords
- ugt
- udp
- reaction
- rebaudioside
- recombinant cells
- Prior art date
Links
- 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 title claims 4
- 239000001776 FEMA 4720 Substances 0.000 title claims 2
- 238000006911 enzymatic reaction Methods 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- 238000000034 method Methods 0.000 claims 10
- 108700023372 Glycosyltransferases Proteins 0.000 claims 9
- 102000051366 Glycosyltransferases Human genes 0.000 claims 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 5
- 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 3
- 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 3
- 125000003275 alpha amino acid group Chemical group 0.000 claims 3
- 239000000348 glycosyl donor Substances 0.000 claims 3
- FWMNVWWHGCHHJJ-SKKKGAJSSA-N 4-amino-1-[(2r)-6-amino-2-[[(2r)-2-[[(2r)-2-[[(2r)-2-amino-3-phenylpropanoyl]amino]-3-phenylpropanoyl]amino]-4-methylpentanoyl]amino]hexanoyl]piperidine-4-carboxylic acid Chemical compound C([C@H](C(=O)N[C@H](CC(C)C)C(=O)N[C@H](CCCCN)C(=O)N1CCC(N)(CC1)C(O)=O)NC(=O)[C@H](N)CC=1C=CC=CC=1)C1=CC=CC=C1 FWMNVWWHGCHHJJ-SKKKGAJSSA-N 0.000 claims 2
- 240000007594 Oryza sativa Species 0.000 claims 2
- 235000007164 Oryza sativa Nutrition 0.000 claims 2
- 244000228451 Stevia rebaudiana Species 0.000 claims 2
- 235000006092 Stevia rebaudiana Nutrition 0.000 claims 2
- 239000008346 aqueous phase Substances 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 239000000386 donor Substances 0.000 claims 2
- 244000005700 microbiome Species 0.000 claims 2
- 230000008929 regeneration Effects 0.000 claims 2
- 238000011069 regeneration method Methods 0.000 claims 2
- CANAPGLEBDTCAF-QHSHOEHESA-N Dulcoside A Natural products C[C@@H]1O[C@H](O[C@@H]2[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]2O[C@]34CC[C@H]5[C@]6(C)CCC[C@](C)([C@H]6CC[C@@]5(CC3=C)C4)C(=O)O[C@@H]7O[C@H](CO)[C@@H](O)[C@H](O)[C@H]7O)[C@H](O)[C@H](O)[C@H]1O CANAPGLEBDTCAF-QHSHOEHESA-N 0.000 claims 1
- CANAPGLEBDTCAF-NTIPNFSCSA-N Dulcoside A 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@]23C(C[C@]4(C2)[C@H]([C@@]2(C)[C@@H]([C@](CCC2)(C)C(=O)O[C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)CC4)CC3)=C)O[C@H](CO)[C@@H](O)[C@@H]1O CANAPGLEBDTCAF-NTIPNFSCSA-N 0.000 claims 1
- 241000588724 Escherichia coli Species 0.000 claims 1
- 241000235058 Komagataella pastoris Species 0.000 claims 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 claims 1
- 235000014680 Saccharomyces cerevisiae Nutrition 0.000 claims 1
- 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 1
- 229930006000 Sucrose Natural products 0.000 claims 1
- 108010043934 Sucrose synthase Proteins 0.000 claims 1
- DRDCJEIZVLVWNC-SLBWPEPYSA-N UDP-beta-L-rhamnose Chemical group O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)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 DRDCJEIZVLVWNC-SLBWPEPYSA-N 0.000 claims 1
- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical group P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 claims 1
- 230000000149 penetrating effect Effects 0.000 claims 1
- 239000002953 phosphate buffered saline Substances 0.000 claims 1
- 239000005720 sucrose Substances 0.000 claims 1
- 125000003944 tolyl group Chemical group 0.000 claims 1
Images
Classifications
-
- 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
-
- 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
- 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
- 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
- C12Y—ENZYMES
- C12Y204/00—Glycosyltransferases (2.4)
- C12Y204/01—Hexosyltransferases (2.4.1)
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biotechnology (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- Microbiology (AREA)
- Genetics & Genomics (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Nutrition Science (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Enzymes And Modification Thereof (AREA)
- Micro-Organisms Or Cultivation Processes Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/CN2016/102910 WO2018072203A1 (zh) | 2016-10-21 | 2016-10-21 | 一种酶法制备瑞鲍迪甙c的方法 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| RU2736155C1 true RU2736155C1 (ru) | 2020-11-12 |
Family
ID=62018093
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2019113355A RU2736155C1 (ru) | 2016-10-21 | 2016-10-21 | Способ получения ребаудиозида c с применением ферментативного способа |
Country Status (9)
| Country | Link |
|---|---|
| US (2) | US11312985B2 (enExample) |
| EP (1) | EP3530746A4 (enExample) |
| JP (1) | JP2019532650A (enExample) |
| CN (2) | CN117051063A (enExample) |
| AU (1) | AU2016427120B2 (enExample) |
| CA (1) | CA3041150A1 (enExample) |
| MX (1) | MX2019004629A (enExample) |
| RU (1) | RU2736155C1 (enExample) |
| WO (1) | WO2018072203A1 (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2011153378A1 (en) * | 2010-06-02 | 2011-12-08 | Abunda Nutrition, Inc. | Recombinant Production of Steviol Glycosides |
| WO2013022989A2 (en) * | 2011-08-08 | 2013-02-14 | Evolva Sa | Recombinant production of steviol glycosides |
| WO2014086890A1 (en) * | 2012-12-05 | 2014-06-12 | Evolva Sa | Steviol glycoside compositions sensory properties |
| US20140357588A1 (en) * | 2013-05-28 | 2014-12-04 | Purecircle Sdn Bhd | High-purity steviol glycosides |
| US9243273B2 (en) * | 2012-05-22 | 2016-01-26 | Purecircle Sdn Bhd | Method for making rebaudioside X |
| RU2596190C2 (ru) * | 2009-10-15 | 2016-08-27 | ПЬЮСЁРКЛ ЭсДиЭн БиЭйчДи | Ребаудиозид d высокой степени чистоты и его применение |
Family Cites Families (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2124633B1 (en) | 2007-01-22 | 2012-03-07 | Cargill, Incorporated | Method of producing purified rebaudioside a compositions using solvent/antisolvent crystallization |
| CN101225424B (zh) | 2007-09-13 | 2013-05-29 | 天津药物研究院 | 环黄芪醇的单葡萄糖苷、其制备方法、药物组合物和应用 |
| PL2350110T3 (pl) | 2008-10-03 | 2016-12-30 | Nowe glikozydy stewiolowe | |
| US8501261B2 (en) | 2010-05-21 | 2013-08-06 | Purecircle Sdn Bhd | High-purity Rebaudioside C and process for purification of the same |
| AU2015261617C1 (en) | 2010-06-02 | 2019-01-31 | Lallemand Bio-Ingredients Usa Llc | Recombinant production of steviol glycosides |
| US8962698B2 (en) | 2011-01-28 | 2015-02-24 | Tate & Lyle Ingredients Americas Llc | Rebaudioside-mogroside V blends |
| CN103031283B (zh) | 2011-10-08 | 2015-07-08 | 成都华高瑞甜科技有限公司 | 甜叶菊酶vi及莱鲍迪苷a转化为莱鲍迪苷d的方法 |
| EP3735841A1 (en) | 2011-12-19 | 2020-11-11 | PureCircle SDN BHD | Methods for purifying steviol glycosides and uses of the same |
| EA201400836A8 (ru) | 2012-01-23 | 2016-03-31 | ДСМ АйПи АССЕТС Б.В. | Получение дитерпена |
| CN103088041B (zh) | 2013-01-29 | 2015-01-07 | 江南大学 | 一种可用于高效生产角质酶的角质酶基因及其应用 |
| KR20150115002A (ko) | 2013-02-06 | 2015-10-13 | 에볼바 에스아 | 레바우디오시드 ｄ 및 레바우디오시드 ｍ의 개선된 생산 방법 |
| CN103397064B (zh) | 2013-08-14 | 2015-04-15 | 苏州汉酶生物技术有限公司 | 一种酶法制备瑞鲍迪甙m的方法 |
| SG2013092820A (en) | 2013-12-16 | 2015-07-30 | Ngee Ann Polytechnic | Xylose isomerase genes for xylose-fermenting yeast construction |
| CN103757074B (zh) * | 2014-01-16 | 2015-12-02 | 苏州汉酶生物技术有限公司 | 一种酶法制备瑞鲍迪甙m的方法 |
| US20170211113A1 (en) | 2014-01-28 | 2017-07-27 | Pepsico, Inc. | Method for preparing rebaudioside m by using enzyme method |
| EP3183349B1 (en) | 2014-08-19 | 2020-03-25 | Purecircle SDN BHD | Method for preparing rebaudioside i |
| CA2987587C (en) | 2015-05-29 | 2022-05-03 | Cargill, Incorporated | Heat treatment to produce glycosides |
| CN105200098A (zh) | 2015-06-30 | 2015-12-30 | 苏州汉酶生物技术有限公司 | 一种利用酿酒酵母酶法制备瑞鲍迪甙m的方法 |
| WO2017031424A1 (en) | 2015-08-20 | 2017-02-23 | Pepsico, Inc. | Preparation of rebaudioside m in a single reaction vessel |
| 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 |
-
2016
- 2016-10-21 EP EP16919508.8A patent/EP3530746A4/en active Pending
- 2016-10-21 WO PCT/CN2016/102910 patent/WO2018072203A1/zh not_active Ceased
- 2016-10-21 CN CN202311021375.1A patent/CN117051063A/zh active Pending
- 2016-10-21 US US16/343,339 patent/US11312985B2/en active Active
- 2016-10-21 MX MX2019004629A patent/MX2019004629A/es unknown
- 2016-10-21 CN CN201680089981.9A patent/CN110199029B/zh active Active
- 2016-10-21 RU RU2019113355A patent/RU2736155C1/ru active
- 2016-10-21 CA CA3041150A patent/CA3041150A1/en active Pending
- 2016-10-21 AU AU2016427120A patent/AU2016427120B2/en active Active
- 2016-10-21 JP JP2019521117A patent/JP2019532650A/ja not_active Withdrawn
-
2022
- 2022-03-30 US US17/657,307 patent/US11976312B2/en active Active
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2596190C2 (ru) * | 2009-10-15 | 2016-08-27 | ПЬЮСЁРКЛ ЭсДиЭн БиЭйчДи | Ребаудиозид d высокой степени чистоты и его применение |
| WO2011153378A1 (en) * | 2010-06-02 | 2011-12-08 | Abunda Nutrition, Inc. | Recombinant Production of Steviol Glycosides |
| WO2013022989A2 (en) * | 2011-08-08 | 2013-02-14 | Evolva Sa | Recombinant production of steviol glycosides |
| US9243273B2 (en) * | 2012-05-22 | 2016-01-26 | Purecircle Sdn Bhd | Method for making rebaudioside X |
| WO2014086890A1 (en) * | 2012-12-05 | 2014-06-12 | Evolva Sa | Steviol glycoside compositions sensory properties |
| US20140357588A1 (en) * | 2013-05-28 | 2014-12-04 | Purecircle Sdn Bhd | High-purity steviol glycosides |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2019532650A (ja) | 2019-11-14 |
| AU2016427120A1 (en) | 2019-05-30 |
| US11312985B2 (en) | 2022-04-26 |
| AU2016427120A8 (en) | 2019-06-06 |
| WO2018072203A1 (zh) | 2018-04-26 |
| US11976312B2 (en) | 2024-05-07 |
| AU2016427120B2 (en) | 2022-08-18 |
| CA3041150A1 (en) | 2018-04-26 |
| US20220220525A1 (en) | 2022-07-14 |
| MX2019004629A (es) | 2019-06-06 |
| CN117051063A (zh) | 2023-11-14 |
| US20190367960A1 (en) | 2019-12-05 |
| CN110199029A (zh) | 2019-09-03 |
| EP3530746A1 (en) | 2019-08-28 |
| CN110199029B (zh) | 2023-09-05 |
| EP3530746A4 (en) | 2020-06-24 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US10428364B2 (en) | Enzymatic method for preparing rebaudioside M | |
| US11976313B2 (en) | Enzymatic method for preparing rebaudioside N | |
| US11952604B2 (en) | Enzymatic method for preparing Rebaudioside J | |
| US11976312B2 (en) | Enzymatic method for preparing Rebaudioside C | |
| JP2019532650A5 (enExample) | ||
| JP7210626B2 (ja) | 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 |