ES2674480T3 - Método para preparar rebaudiósido A a partir de esteviósido - Google Patents
Método para preparar rebaudiósido A a partir de esteviósido Download PDFInfo
- Publication number
- ES2674480T3 ES2674480T3 ES13876125.9T ES13876125T ES2674480T3 ES 2674480 T3 ES2674480 T3 ES 2674480T3 ES 13876125 T ES13876125 T ES 13876125T ES 2674480 T3 ES2674480 T3 ES 2674480T3
- Authority
- ES
- Spain
- Prior art keywords
- stevioside
- rebaudioside
- preparing rebaudioside
- preparing
- nucleotide diphosphate
- 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.)
- Active
Links
- 239000001512 FEMA 4601 Substances 0.000 title abstract 2
- 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 title abstract 2
- 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 title abstract 2
- 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 title abstract 2
- 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 title abstract 2
- 235000019203 rebaudioside A Nutrition 0.000 title abstract 2
- 229940013618 stevioside Drugs 0.000 title abstract 2
- 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 title abstract 2
- 235000019202 steviosides Nutrition 0.000 title abstract 2
- 108010043934 Sucrose synthase Proteins 0.000 abstract description 2
- 239000001177 diphosphate Substances 0.000 abstract 3
- XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical compound [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 abstract 3
- 235000011180 diphosphates Nutrition 0.000 abstract 3
- 239000002773 nucleotide Substances 0.000 abstract 3
- 125000003729 nucleotide group Chemical group 0.000 abstract 3
- 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 abstract 2
- 239000008103 glucose Substances 0.000 abstract 2
- 108700023372 Glycosyltransferases Proteins 0.000 abstract 1
- 102000051366 Glycosyltransferases Human genes 0.000 abstract 1
- GIPHUOWOTCAJSR-UHFFFAOYSA-N Rebaudioside A. 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)C1OC(C1O)OC(CO)C(O)C1OC1OC(CO)C(O)C(O)C1O GIPHUOWOTCAJSR-UHFFFAOYSA-N 0.000 abstract 1
- 229930006000 Sucrose Natural products 0.000 abstract 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 abstract 1
- 239000005720 sucrose Substances 0.000 abstract 1
Classifications
-
- 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
- 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
-
- 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
-
- 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)
- 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
- C12N9/10—Transferases (2.)
- 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
- C12Y—ENZYMES
- C12Y204/00—Glycosyltransferases (2.4)
- C12Y204/01—Hexosyltransferases (2.4.1)
- C12Y204/01013—Sucrose synthase (2.4.1.13)
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Genetics & Genomics (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- General Engineering & Computer Science (AREA)
- Biotechnology (AREA)
- Microbiology (AREA)
- Molecular Biology (AREA)
- Biomedical Technology (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Enzymes And Modification Thereof (AREA)
- Saccharide Compounds (AREA)
Abstract
Un método para preparar rebaudiósido A, que comprende: (1) hacer reaccionar sacarosa y nucleótido difosfato en presencia de sacarosa sintasa para preparar nucleótido difosfato al que se ha unido la glucosa; y (2) hacer reaccionar el nucleótido difosfato al cual se ha unido glucosa con esteviósido en presencia de glicosiltransferasa para preparar rebaudiósido A.
Description
11
<210> 3
<211> 808
<212> PRT
<213> Sacarosa sintasa
<400> 3
13
15
18
Claims (1)
-
imagen1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1020130022176A KR101404728B1 (ko) | 2013-02-28 | 2013-02-28 | 스테비오사이드로부터 리바우디오사이드 a를 제조하는 방법 |
| KR20130022176 | 2013-02-28 | ||
| PCT/KR2013/011330 WO2014133248A1 (ko) | 2013-02-28 | 2013-12-09 | 스테비오사이드로부터 리바우디오사이드 a를 제조하는 방법 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2674480T3 true ES2674480T3 (es) | 2018-07-02 |
Family
ID=51132132
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES13876125.9T Active ES2674480T3 (es) | 2013-02-28 | 2013-12-09 | Método para preparar rebaudiósido A a partir de esteviósido |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US10472660B2 (es) |
| EP (1) | EP2963122B1 (es) |
| JP (2) | JP6147370B2 (es) |
| KR (1) | KR101404728B1 (es) |
| CN (1) | CN105164270B8 (es) |
| ES (1) | ES2674480T3 (es) |
| WO (1) | WO2014133248A1 (es) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9522929B2 (en) | 2014-05-05 | 2016-12-20 | Conagen Inc. | Non-caloric sweetener |
| CA2979931A1 (en) | 2015-03-16 | 2016-09-22 | Dsm Ip Assets B.V. | Udp-glycosyltransferases |
| JP6793957B2 (ja) * | 2015-04-14 | 2020-12-02 | コナゲン インコーポレイテッド | 改変された全細胞触媒を用いたノンカロリー甘味料の生成 |
| US20170266524A1 (en) * | 2016-03-18 | 2017-09-21 | James C. Van Loon, III | Method of using lacrosse mesh |
| WO2017207484A1 (en) | 2016-05-31 | 2017-12-07 | Universiteit Gent | Mutant sucrose synthases and their uses |
| KR20190017045A (ko) * | 2016-06-15 | 2019-02-19 | 코덱시스, 인코포레이티드 | 글루코스-1-포스페이트에 의한 스테비올 글리코시드 및 다른 화합물의 효소 글리코실화 |
| MX2018015534A (es) | 2016-06-15 | 2019-03-14 | Codexis Inc | Beta-glucosidasas dise?adas y metodos de glucosilacion. |
| AU2017308143B2 (en) | 2016-08-12 | 2022-04-07 | Amyris, Inc. | UDP-dependent glycosyltransferase for high efficiency production of rebaudiosides |
| CA3175070A1 (en) | 2017-02-03 | 2018-08-09 | Codexis, Inc. | Engineered glycosyltransferases and steviol glycoside glucosylation methods |
| CN108315394A (zh) * | 2018-04-23 | 2018-07-24 | 沈阳师范大学 | 甜高粱蔗糖合成酶基因的表达检测方法及扩增引物 |
| CN109196110A (zh) * | 2018-07-19 | 2019-01-11 | 邦泰生物工程(深圳)有限公司 | 莱苞迪甙a的制备方法、莱苞迪甙a制备用酶及应用 |
| WO2020028039A1 (en) | 2018-07-30 | 2020-02-06 | Codexis, Inc. | Engineered glycosyltransferases and steviol glycoside glucosylation methods |
| CN113302298B (zh) | 2018-11-09 | 2025-02-25 | 银杏生物制品公司 | 罗汉果甙的生物合成 |
| 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 |
| KR102303415B1 (ko) * | 2019-06-14 | 2021-09-23 | 씨제이제일제당 (주) | 감미 소재 조성물 및 이의 제조 방법 |
| CN111621456A (zh) * | 2020-05-25 | 2020-09-04 | 安徽金禾实业股份有限公司 | 一种液态发酵制备莱鲍迪苷a的方法 |
| CN111593062A (zh) * | 2020-05-25 | 2020-08-28 | 安徽金禾实业股份有限公司 | 一种利用枯草芽孢杆菌发酵催化制备莱鲍迪苷a的方法 |
| KR102628374B1 (ko) * | 2021-10-19 | 2024-01-24 | 씨제이제일제당 주식회사 | 신규한 당전이효소 및 이의 용도 |
| EP4417699A4 (en) * | 2021-10-19 | 2025-12-24 | Cj Cheiljedang Corp | PROCESS FOR THE PRODUCTION OF REBAUDIOSIDE D AND REBAUDIOSIDE M |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4219571A (en) * | 1978-06-15 | 1980-08-26 | Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenkyujo | Process for producing a sweetener |
| JPS58149697A (ja) * | 1982-02-27 | 1983-09-06 | Dainippon Ink & Chem Inc | β−１，３グリコシルステビオシドの製造方法 |
| JPH11290075A (ja) * | 1998-02-26 | 1999-10-26 | Univ Kyoto | 組み換えミュータントシュクロース合成酵素によるシュクロースからのセルロースの合成 |
| JP2000245279A (ja) * | 1999-03-01 | 2000-09-12 | Mitsui Chemicals Inc | 植物の耐冷性の増強方法 |
| US6469947B2 (en) | 1999-06-29 | 2002-10-22 | Hyundai Electronics Co., Ltd. | Semiconductor memory device having regions with independent word lines alternately selected for refresh operation |
| KR20040026747A (ko) | 2002-09-26 | 2004-04-01 | 바이오스펙트럼 주식회사 | 미생물을 이용한 리보디오사이드 에이의 제조방법 |
| WO2006093229A1 (ja) | 2005-03-04 | 2006-09-08 | Morita Kagaku Kogyo Co., Ltd. | ステビア甘味料 |
| FR2887253A1 (fr) | 2005-06-20 | 2006-12-22 | Phosphoenix Sarl | Nouvelles arylphosphines p chirales ortho-fonctionnalisees et derives: leur preparation et utilisation en catalyse asymetrique |
| JP2007330112A (ja) * | 2006-06-12 | 2007-12-27 | Sanei Gen Ffi Inc | フェノール性化合物のグルコース配糖体の製造方法 |
| JP5307730B2 (ja) * | 2007-01-22 | 2013-10-02 | カーギル・インコーポレイテッド | 溶媒／貧溶媒晶析を用いる精製レバウディオサイドａ組成物の製法 |
| US9005444B2 (en) | 2008-05-13 | 2015-04-14 | Cargill, Incorporated | Separation of rebaudioside A from stevia glycosides using chromatography |
| KR101598935B1 (ko) * | 2010-04-16 | 2016-03-03 | 씨제이제일제당(주) | 레바우디오사이드 ａ의 생산 공정에서 발생하는 부산물을 재활용하여 고수득율의 레바우디오사이드 ａ를 제조하는 방법 |
| CN105671108A (zh) | 2010-06-02 | 2016-06-15 | 沃维公司 | 甜菊糖苷的重组生产 |
| CN108396044A (zh) * | 2011-08-08 | 2018-08-14 | 埃沃尔瓦公司 | 甜菊醇糖苷类的重组生产 |
| CN102766667B (zh) * | 2012-08-14 | 2014-06-11 | 成都南诺格生物科技有限责任公司 | 甜菊苷转化为莱鲍迪苷e的方法 |
-
2013
- 2013-02-28 KR KR1020130022176A patent/KR101404728B1/ko active Active
- 2013-12-09 ES ES13876125.9T patent/ES2674480T3/es active Active
- 2013-12-09 JP JP2015560087A patent/JP6147370B2/ja active Active
- 2013-12-09 EP EP13876125.9A patent/EP2963122B1/en active Active
- 2013-12-09 CN CN201380073982.0A patent/CN105164270B8/zh active Active
- 2013-12-09 WO PCT/KR2013/011330 patent/WO2014133248A1/ko not_active Ceased
- 2013-12-09 US US14/770,962 patent/US10472660B2/en active Active
-
2017
- 2017-03-10 JP JP2017046085A patent/JP2017148050A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| JP6147370B2 (ja) | 2017-06-21 |
| WO2014133248A1 (ko) | 2014-09-04 |
| EP2963122A1 (en) | 2016-01-06 |
| CN105164270A (zh) | 2015-12-16 |
| US20160010133A1 (en) | 2016-01-14 |
| JP2016508378A (ja) | 2016-03-22 |
| CN105164270B8 (zh) | 2019-12-06 |
| CN105164270B (zh) | 2019-07-09 |
| KR101404728B1 (ko) | 2014-06-09 |
| JP2017148050A (ja) | 2017-08-31 |
| EP2963122A4 (en) | 2016-10-12 |
| US10472660B2 (en) | 2019-11-12 |
| EP2963122B1 (en) | 2018-05-30 |
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