MX2016001986A - Metodo para preparar rebaudiosido m mediante el uso de un metodo con enzima. - Google Patents
Metodo para preparar rebaudiosido m mediante el uso de un metodo con enzima.Info
- Publication number
- MX2016001986A MX2016001986A MX2016001986A MX2016001986A MX2016001986A MX 2016001986 A MX2016001986 A MX 2016001986A MX 2016001986 A MX2016001986 A MX 2016001986A MX 2016001986 A MX2016001986 A MX 2016001986A MX 2016001986 A MX2016001986 A MX 2016001986A
- Authority
- MX
- Mexico
- Prior art keywords
- rebaudioside
- enzyme
- preparing rebaudioside
- preparing
- glucosyltransferase
- Prior art date
Links
- 238000000034 method Methods 0.000 title abstract 5
- GSGVXNMGMKBGQU-PHESRWQRSA-N rebaudioside M Chemical compound C[C@@]12CCC[C@](C)([C@H]1CC[C@@]13CC(=C)[C@@](C1)(CC[C@@H]23)O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@H]1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)C(=O)O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@H]1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O GSGVXNMGMKBGQU-PHESRWQRSA-N 0.000 title abstract 3
- 102000004190 Enzymes Human genes 0.000 title abstract 2
- 108090000790 Enzymes Proteins 0.000 title abstract 2
- 101710204244 Processive diacylglycerol beta-glucosyltransferase Proteins 0.000 abstract 2
- 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 abstract 2
- 239000000758 substrate Substances 0.000 abstract 2
- 239000001512 FEMA 4601 Substances 0.000 abstract 1
- 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 abstract 1
- 238000006555 catalytic reaction Methods 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 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 abstract 1
- 125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 abstract 1
- 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 abstract 1
- 235000019203 rebaudioside A Nutrition 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
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- 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
- 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
- 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
- C12Y—ENZYMES
- C12Y204/00—Glycosyltransferases (2.4)
- C12Y204/01—Hexosyltransferases (2.4.1)
- C12Y204/01017—Glucuronosyltransferase (2.4.1.17)
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Genetics & Genomics (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- General Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Microbiology (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Molecular Biology (AREA)
- Biomedical Technology (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Food Science & Technology (AREA)
- Nutrition Science (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Enzymes And Modification Thereof (AREA)
- Micro-Organisms Or Cultivation Processes Thereof (AREA)
Abstract
Se proporciona un método para preparar rebaudiósido M mediante el uso de un método con enzima. En el método, el rebaudiósido A o rebaudiósido D se usa como un substrato; y en la existencia de un donador de glucosilo, se genera rebaudiósido M por medio de la reacción del substrato bajo la catálisis de UDP-glucosiltransferas a y/o células recombinantes que contienen la UDP-glucosiltransfera sa.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201310353500.9A CN103397064B (zh) | 2013-08-14 | 2013-08-14 | 一种酶法制备瑞鲍迪甙m的方法 |
| PCT/CN2013/084644 WO2015021690A1 (zh) | 2013-08-14 | 2013-09-29 | 一种酶法制备瑞鲍迪甙m的方法 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| MX2016001986A true MX2016001986A (es) | 2016-10-26 |
Family
ID=49560764
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MX2016001986A MX2016001986A (es) | 2013-08-14 | 2013-09-29 | Metodo para preparar rebaudiosido m mediante el uso de un metodo con enzima. |
Country Status (11)
| Country | Link |
|---|---|
| US (2) | US10301662B2 (es) |
| EP (1) | EP3034614A4 (es) |
| JP (1) | JP6272485B2 (es) |
| CN (1) | CN103397064B (es) |
| AU (1) | AU2013398146B2 (es) |
| BR (1) | BR112016003035A2 (es) |
| CA (1) | CA2921247C (es) |
| HK (1) | HK1226103A1 (es) |
| MX (1) | MX2016001986A (es) |
| RU (1) | RU2658436C2 (es) |
| WO (1) | WO2015021690A1 (es) |
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| BR122021005283B1 (pt) | 2010-06-02 | 2022-02-22 | Evolva, Inc | Hospedeiro recombinante que compreende genes recombinantes para produção deesteviol ou glicosídeo de esteviol, método para produzir esteviol, glicosídeo de esteviol ou composição de glicosídeo de esteviol e método para sintetizar esteviol ou glicosídeo de esteviol |
| EP3009508B1 (en) | 2011-08-08 | 2020-11-25 | Evolva SA | Recombinant production of steviol glycosides |
| MX352678B (es) | 2012-05-22 | 2017-12-04 | Purecircle Sdn Bhd | Glucosidos de esteviol de alta pureza. |
| US9752174B2 (en) | 2013-05-28 | 2017-09-05 | Purecircle Sdn Bhd | High-purity steviol glycosides |
| CA2899276C (en) | 2013-02-06 | 2022-11-01 | Evolva Sa | Methods for improved production of rebaudioside d and rebaudioside m |
| US10017804B2 (en) | 2013-02-11 | 2018-07-10 | Evolva Sa | Efficient production of steviol glycosides in recombinant hosts |
| 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 |
| CN106471128A (zh) * | 2014-01-28 | 2017-03-01 | 百事可乐公司 | 一种酶法制备瑞鲍迪甙m的方法 |
| US9522929B2 (en) | 2014-05-05 | 2016-12-20 | Conagen Inc. | Non-caloric sweetener |
| CN105087739B (zh) * | 2014-05-12 | 2019-11-05 | 中国科学院上海生命科学研究院 | 一种新的制备稀有人参皂苷的催化体系及其应用 |
| CN104163839A (zh) * | 2014-07-04 | 2014-11-26 | 苏州景泓生物技术有限公司 | 一种制备莱鲍迪苷m的工艺方法 |
| JP2017528125A (ja) | 2014-08-11 | 2017-09-28 | エヴォルヴァ エスアー．Ｅｖｏｌｖａ Ｓａ． | 組み換え宿主におけるステビオールグリコシドの産生 |
| CN104151378A (zh) * | 2014-08-12 | 2014-11-19 | 济南汉定生物工程有限公司 | 一种甜菊糖甙rm的提纯方法 |
| JP2017528134A (ja) | 2014-09-09 | 2017-09-28 | エヴォルヴァ エスアー．Ｅｖｏｌｖａ Ｓａ． | 組み換え宿主におけるステビオールグリコシドの生産 |
| CN104232496B (zh) * | 2014-09-18 | 2017-06-06 | 广州康琳奈生物科技有限公司 | 一种重组毕赤酵母工程菌及其在合成莱鲍迪苷a中的应用 |
| MY182725A (en) * | 2014-10-03 | 2021-02-03 | Conagen Inc | Non-caloric sweeteners and methods for synthesizing |
| US10463062B2 (en) * | 2014-11-05 | 2019-11-05 | Manus Bio Inc. | Microbial production of steviol glycosides |
| SG11201705606PA (en) | 2015-01-30 | 2017-08-30 | Evolva Sa | Production of steviol glycosides in recombinant hosts |
| EP3271457B1 (en) | 2015-03-16 | 2021-01-20 | DSM IP Assets B.V. | Udp-glycosyltransferases |
| CN104726523B (zh) * | 2015-03-28 | 2018-08-10 | 南京工业大学 | 一种酶法制备莱鲍迪苷m的方法 |
| MX2017013210A (es) | 2015-04-14 | 2018-03-01 | Conagen Inc | Produccion de endulzantes no caloricos con catalizadores de celulas enteras modificadas. |
| 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 |
| EP3332018B1 (en) | 2015-08-07 | 2022-07-27 | Evolva SA | Production of steviol glycosides in recombinant hosts |
| US20200308616A1 (en) * | 2015-11-30 | 2020-10-01 | Purecircle Sdn Bhd | Process for producing high purity steviol glycosides |
| CN109195457A (zh) | 2016-04-13 | 2019-01-11 | 埃沃尔瓦公司 | 在重组宿主中产生甜菊醇糖苷 |
| US10815514B2 (en) | 2016-05-16 | 2020-10-27 | Evolva Sa | Production of steviol glycosides in recombinant hosts |
| BR112018075932A2 (pt) | 2016-06-15 | 2019-10-01 | Codexis Inc | variante de beta-glicosidase de ocorrência não natural, polinucleotídeo recombinante, vetor, célula hospedeira, métodos para produção de pelo menos uma variante de beta-glicosidade de ocorrência não natural, para conversão de um substrato aceptor de grupo glicosila em um produto beta-glicosilado e para transglicosilação de um substrato, e, composição. |
| CN110191643B (zh) * | 2016-10-14 | 2023-06-06 | 科纳根公司 | 甜菊醇糖苷的生物合成生产及其工艺 |
| CN116574775A (zh) | 2016-10-21 | 2023-08-11 | 百事可乐公司 | 一种酶法制备瑞鲍迪甙j的方法 |
| CA3041152A1 (en) * | 2016-10-21 | 2018-04-26 | Pepsico, Inc. | Method for preparing rebaudioside n using enzymatic method |
| JP2019532650A (ja) | 2016-10-21 | 2019-11-14 | ペプシコ・インク | 酵素法を使用することによりレバウディオサイドｃを調製するための方法 |
| WO2018083338A1 (en) | 2016-11-07 | 2018-05-11 | Evolva Sa | Production of steviol glycosides in recombinant hosts |
| CA3050310A1 (en) | 2017-02-03 | 2018-08-09 | Codexis, Inc. | Engineered glycosyltransferases and steviol glycoside glucosylation methods |
| MY202423A (en) * | 2017-03-06 | 2024-04-28 | Conagen Inc | Biosynthetic production of steviol glycoside rebaudioside d4 from rebaudioside e |
| US11284577B2 (en) | 2017-03-08 | 2022-03-29 | Purecircle Usa Inc. | High rebaudioside M stevia plant cultivars and methods of producing the same |
| CN106866757B (zh) | 2017-03-16 | 2020-06-26 | 诸城市浩天药业有限公司 | 甜菊糖m苷晶型及制备方法和用途 |
| PE20200291A1 (es) * | 2017-05-15 | 2020-02-05 | Purecircle Usa Inc | Glicosidos de esteviol de alta pureza |
| AU2018294258A1 (en) | 2017-06-30 | 2020-02-06 | Conagen Inc. | Hydrolysis of steviol glycosides by beta-glucosidase |
| CN107586809A (zh) * | 2017-10-09 | 2018-01-16 | 中国科学院天津工业生物技术研究所 | 一种生物催化合成大豆低聚糖的方法 |
| CN108998485A (zh) * | 2018-06-28 | 2018-12-14 | 青岛润德生物科技有限公司 | 一种甜菊糖苷复合物及其制备方法 |
| JP7305087B2 (ja) * | 2018-07-16 | 2023-07-10 | マナス バイオ インコーポレイテッド | 全細胞生体内変換によるステビオールグリコシドの産生 |
| CN109393426A (zh) * | 2018-09-29 | 2019-03-01 | 四川盈嘉合生科技有限公司 | 一种复合甜味剂 |
| CN109234341A (zh) * | 2018-09-29 | 2019-01-18 | 四川盈嘉合生科技有限公司 | 全细胞催化合成甜味剂组合物的方法 |
| CN111073923A (zh) * | 2018-10-22 | 2020-04-28 | 山东三元生物科技股份有限公司 | 一种莱鲍迪苷m的酶法制备方法 |
| CN109588686A (zh) * | 2018-10-31 | 2019-04-09 | 郑书旺 | 一种复合甜味剂及其制备方法 |
| CN115478060B (zh) * | 2021-06-16 | 2023-11-28 | 弈柯莱生物科技(集团)股份有限公司 | 一种糖基转移酶及其应用 |
| KR102628374B1 (ko) * | 2021-10-19 | 2024-01-24 | 씨제이제일제당 주식회사 | 신규한 당전이효소 및 이의 용도 |
| CN114164191B (zh) * | 2021-11-17 | 2024-03-01 | 江南大学 | 一种利用糖基转移酶高效生物合成莱鲍迪苷d的方法 |
| CN118064459A (zh) * | 2022-05-27 | 2024-05-24 | 中化健康产业发展有限公司 | 一种催化Reb A生产Reb M的重组糖基转移酶 |
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| BRPI0807794A2 (pt) | 2007-01-22 | 2014-07-01 | Cargill Inc | Método de proução de composições de rebaudiosídeo a purificado usando cristalização com solvente/antisolvente. |
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| KR102061165B1 (ko) * | 2008-10-03 | 2019-12-31 | 모리타 가가쿠 고교 가부시키가이샤 | 신규 스테비올 배당체 |
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| BR122021005283B1 (pt) * | 2010-06-02 | 2022-02-22 | Evolva, Inc | Hospedeiro recombinante que compreende genes recombinantes para produção deesteviol ou glicosídeo de esteviol, método para produzir esteviol, glicosídeo de esteviol ou composição de glicosídeo de esteviol e método para sintetizar esteviol ou glicosídeo de esteviol |
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| ES2971273T3 (es) | 2011-12-19 | 2024-06-04 | Coca Cola Co | Bebida que comprende rebaudiósido X |
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| CN102559528B (zh) * | 2012-02-09 | 2013-08-21 | 南京工业大学 | 一种产甜叶菊糖基转移酶ugt76g1的基因工程菌及其应用 |
| US9752174B2 (en) | 2013-05-28 | 2017-09-05 | Purecircle Sdn Bhd | High-purity steviol glycosides |
| MX352678B (es) * | 2012-05-22 | 2017-12-04 | Purecircle Sdn Bhd | Glucosidos de esteviol de alta pureza. |
| WO2014086890A1 (en) | 2012-12-05 | 2014-06-12 | Evolva Sa | Steviol glycoside compositions sensory properties |
| 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 |
| CA2899276C (en) | 2013-02-06 | 2022-11-01 | Evolva Sa | Methods for improved production of rebaudioside d and rebaudioside m |
| 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 |
| CN106471128A (zh) | 2014-01-28 | 2017-03-01 | 百事可乐公司 | 一种酶法制备瑞鲍迪甙m的方法 |
| EP4063513A1 (en) | 2015-05-29 | 2022-09-28 | Cargill, Incorporated | Heat treatment to produce glycosides |
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2013
- 2013-08-14 CN CN201310353500.9A patent/CN103397064B/zh active Active
- 2013-09-29 JP JP2016533776A patent/JP6272485B2/ja active Active
- 2013-09-29 EP EP13891561.6A patent/EP3034614A4/en active Pending
- 2013-09-29 RU RU2016108660A patent/RU2658436C2/ru active
- 2013-09-29 CA CA2921247A patent/CA2921247C/en active Active
- 2013-09-29 AU AU2013398146A patent/AU2013398146B2/en active Active
- 2013-09-29 BR BR112016003035-4A patent/BR112016003035A2/pt not_active Application Discontinuation
- 2013-09-29 WO PCT/CN2013/084644 patent/WO2015021690A1/zh active Application Filing
- 2013-09-29 MX MX2016001986A patent/MX2016001986A/es active IP Right Grant
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2016
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|---|---|
| RU2016108660A (ru) | 2017-09-18 |
| CA2921247C (en) | 2021-04-06 |
| EP3034614A4 (en) | 2017-04-12 |
| AU2013398146B2 (en) | 2017-07-13 |
| CN103397064B (zh) | 2015-04-15 |
| CN103397064A (zh) | 2013-11-20 |
| WO2015021690A1 (zh) | 2015-02-19 |
| US10428364B2 (en) | 2019-10-01 |
| HK1226103A1 (zh) | 2017-09-22 |
| CA2921247A1 (en) | 2015-02-19 |
| JP6272485B2 (ja) | 2018-01-31 |
| US20190233866A1 (en) | 2019-08-01 |
| AU2013398146A1 (en) | 2016-04-07 |
| EP3034614A1 (en) | 2016-06-22 |
| BR112016003035A2 (pt) | 2018-02-06 |
| US20160298159A1 (en) | 2016-10-13 |
| RU2658436C2 (ru) | 2018-06-21 |
| US10301662B2 (en) | 2019-05-28 |
| JP2016527892A (ja) | 2016-09-15 |
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