MX2019015404A - Hidrólisis de glucósidos de esteviol por beta-glucosidasa. - Google Patents
Hidrólisis de glucósidos de esteviol por beta-glucosidasa.Info
- Publication number
- MX2019015404A MX2019015404A MX2019015404A MX2019015404A MX2019015404A MX 2019015404 A MX2019015404 A MX 2019015404A MX 2019015404 A MX2019015404 A MX 2019015404A MX 2019015404 A MX2019015404 A MX 2019015404A MX 2019015404 A MX2019015404 A MX 2019015404A
- Authority
- MX
- Mexico
- Prior art keywords
- reb
- cells
- steviol glycosides
- rebaudioside
- glucosidase
- Prior art date
Links
- 235000019202 steviosides Nutrition 0.000 title abstract 7
- 239000004383 Steviol glycoside Substances 0.000 title abstract 5
- 229930182488 steviol glycoside Natural products 0.000 title abstract 5
- 235000019411 steviol glycoside Nutrition 0.000 title abstract 5
- 150000008144 steviol glycosides Chemical class 0.000 title abstract 5
- 102000006995 beta-Glucosidase Human genes 0.000 title abstract 2
- 108010047754 beta-Glucosidase Proteins 0.000 title abstract 2
- 230000007062 hydrolysis Effects 0.000 title 1
- 238000006460 hydrolysis reaction Methods 0.000 title 1
- 238000000034 method Methods 0.000 abstract 4
- 230000000813 microbial effect Effects 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
- 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 abstract 1
- 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 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
- 230000007071 enzymatic hydrolysis Effects 0.000 abstract 1
- 238000006047 enzymatic hydrolysis reaction Methods 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 108090000623 proteins and genes Proteins 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
- 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 abstract 1
- 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 abstract 1
- 229940013618 stevioside Drugs 0.000 abstract 1
- 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 abstract 1
- 239000000758 substrate Substances 0.000 abstract 1
- 239000002699 waste material Substances 0.000 abstract 1
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
- A23L5/00—Preparation or treatment of foods or foodstuffs, in general; Food or foodstuffs obtained thereby; Materials therefor
- A23L5/20—Removal of unwanted matter, e.g. deodorisation or detoxification
- A23L5/25—Removal of unwanted matter, e.g. deodorisation or detoxification using enzymes
-
- 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 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
-
- 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
- A23L27/36—Terpene glycosides
-
- 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
- A23L5/00—Preparation or treatment of foods or foodstuffs, in general; Food or foodstuffs obtained thereby; Materials therefor
- A23L5/20—Removal of unwanted matter, e.g. deodorisation or detoxification
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar 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
-
- 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
- C12P19/14—Preparation of compounds containing saccharide radicals produced by the action of a carbohydrase (EC 3.2.x), e.g. by alpha-amylase, e.g. by cellulase, hemicellulase
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12Y—ENZYMES
- C12Y302/00—Hydrolases acting on glycosyl compounds, i.e. glycosylases (3.2)
- C12Y302/01—Glycosidases, i.e. enzymes hydrolysing O- and S-glycosyl compounds (3.2.1)
- C12Y302/01015—Polygalacturonase (3.2.1.15)
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12Y—ENZYMES
- C12Y302/00—Hydrolases acting on glycosyl compounds, i.e. glycosylases (3.2)
- C12Y302/01—Glycosidases, i.e. enzymes hydrolysing O- and S-glycosyl compounds (3.2.1)
- C12Y302/01021—Beta-glucosidase (3.2.1.21)
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12Y—ENZYMES
- C12Y302/00—Hydrolases acting on glycosyl compounds, i.e. glycosylases (3.2)
- C12Y302/01—Glycosidases, i.e. enzymes hydrolysing O- and S-glycosyl compounds (3.2.1)
- C12Y302/01023—Beta-galactosidase (3.2.1.23), i.e. exo-(1-->4)-beta-D-galactanase
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Biotechnology (AREA)
- General Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Microbiology (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Molecular Biology (AREA)
- Nutrition Science (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Enzymes And Modification Thereof (AREA)
- Micro-Organisms Or Cultivation Processes Thereof (AREA)
- Seasonings (AREA)
Abstract
La presente descripción proporciona un método para producir cantidades mejoradas de rebaudiósido M (Reb M) a partir de diversos glucósidos de esteviol utilizando la actividad hidrolítica de la beta-glucosidasa. Más específicamente, la presente descripción proporciona un proceso mejorado para producir glucósidos de esteviol deseados a partir de células recombinantes alteradas (por ejemplo, células microbianas recombinantes) que contienen sustratos de interés. Aquí es donde tales células (por ejemplo, microbios) se han modificado para transportar genes capaces de generar glucósidos de esteviol de interés, incluido el rebaudiósido A (Reb A), el rebaudiósido E (Reb E) y/o el esteviósido. En esta modalidad, el proceso comprende las etapas de obtener el material de células alteradas (por ejemplo, células microbianas) y llevar a cabo una hidrólisis enzimática en los esteviósidos presentes en dicho producto de desecho para mejorar la producción de Reb M. Además se proporcionan composiciones de glucósido de esteviol producidas por los métodos descritos aquí.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201762527482P | 2017-06-30 | 2017-06-30 | |
| PCT/US2018/040193 WO2019006244A1 (en) | 2017-06-30 | 2018-06-29 | HYDROLYSIS OF STEVIOL GLYCOSIDES BY BETA-GLUCOSIDASE |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| MX2019015404A true MX2019015404A (es) | 2020-07-20 |
Family
ID=64742225
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MX2019015404A MX2019015404A (es) | 2017-06-30 | 2018-06-29 | Hidrólisis de glucósidos de esteviol por beta-glucosidasa. |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US11414689B2 (es) |
| EP (1) | EP3644758A4 (es) |
| JP (1) | JP7116751B2 (es) |
| KR (1) | KR102792406B1 (es) |
| CN (1) | CN110809408B (es) |
| AU (1) | AU2018294258A1 (es) |
| BR (1) | BR112019027992B1 (es) |
| CA (1) | CA3068440A1 (es) |
| MX (1) | MX2019015404A (es) |
| MY (1) | MY204670A (es) |
| WO (1) | WO2019006244A1 (es) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MX389746B (es) | 2014-09-19 | 2025-03-20 | Purecircle Sdn Bhd | Esteviol glicosidos de alta pureza. |
| RU2019114181A (ru) | 2016-10-14 | 2020-11-16 | Конаджен Инк. | Биосинтетическое получение стевиоловых гликозидов и связанные с этим способы |
| AU2018413277B2 (en) * | 2018-03-16 | 2024-07-11 | Purecircle Usa Inc. | High-purity steviol glycosides |
| MX2020009635A (es) * | 2018-03-16 | 2021-02-16 | Purecircle Usa Inc | Glucosidos de esteviol de alta pureza. |
| CN110564658B (zh) * | 2019-09-06 | 2021-08-17 | 广西大学 | 一株大肠杆菌工程菌及其全细胞催化生产甜菊醇的方法 |
| CN113930377B (zh) * | 2021-10-14 | 2023-12-26 | 广西大学 | 一株全细胞催化提高莱鲍迪苷a含量的工程菌 |
| CN116286750A (zh) * | 2023-05-15 | 2023-06-23 | 新余学院 | 一种β-葡萄糖苷酶、编码基因、重组载体、工程菌及应用 |
Family Cites Families (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3761236B2 (ja) * | 1995-12-20 | 2006-03-29 | 天野エンザイム株式会社 | 新規なβ−グルコシダーゼ、その製造法および用途 |
| US8507022B2 (en) | 2009-10-15 | 2013-08-13 | Purecircle Sdn Bhd | High-purity rebaudioside D and low-calorie carbonated lemon-flavored beverage containing the same |
| WO2014185931A1 (en) * | 2013-05-15 | 2014-11-20 | Purecircle Usa, Inc. | Stevia composition |
| BR122021015509B1 (pt) * | 2011-08-08 | 2022-03-29 | Evolva Sa | Método para produzir um glicosídeo de esteviol alvo |
| WO2013026151A1 (en) * | 2011-08-19 | 2013-02-28 | Justbio Inc. | Improved stevia rebaudiana extract and formulation, and uses thereof |
| US9752174B2 (en) | 2013-05-28 | 2017-09-05 | Purecircle Sdn Bhd | High-purity steviol glycosides |
| CN102827891B (zh) * | 2012-09-21 | 2014-01-22 | 江南大学 | 用β-葡萄糖苷酶催化水解甜菊苷制备甜菊醇的方法 |
| CN102925518A (zh) | 2012-10-31 | 2013-02-13 | 江南大学 | 一种用甜菊苷制备甜菊双糖苷的方法 |
| CN105051195B (zh) | 2013-02-06 | 2019-09-06 | 埃沃尔瓦公司 | 用于提高莱鲍迪苷d和莱鲍迪苷m之产生的方法 |
| BR112015029487A8 (pt) | 2013-06-19 | 2019-12-17 | Phyto Tech Corp | rebaudiosídeo-e e produtos alimentícios adoçados com rebaudiosídeo-e |
| 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 |
| EP3063286B1 (en) | 2013-11-01 | 2018-12-05 | Conagen Inc. | Recombinant production of steviol glycosides |
| US9522929B2 (en) | 2014-05-05 | 2016-12-20 | Conagen Inc. | Non-caloric sweetener |
| EP2957182A1 (en) * | 2014-06-18 | 2015-12-23 | Technische Hochschule Mittelhessen | Improved natural sweetener compositions |
| MX389746B (es) * | 2014-09-19 | 2025-03-20 | Purecircle Sdn Bhd | Esteviol glicosidos de alta pureza. |
| MX368414B (es) | 2014-10-03 | 2019-10-02 | Conagen Inc | Edulcorantes no caloricos y metodos para sintetizar. |
| WO2016073740A1 (en) | 2014-11-05 | 2016-05-12 | Manus Biosynthesis, Inc. | Microbial production of steviol glycosides |
| US10058112B2 (en) * | 2014-11-21 | 2018-08-28 | Eco Sweeteners Llc | Sweetener composition including enzymatically processed stevia and method of manufacturing |
| CA2973674A1 (en) | 2015-01-30 | 2016-08-04 | Evolva Sa | Production of steviol glycosides in recombinant hosts |
| CN107920548A (zh) * | 2015-08-06 | 2018-04-17 | 嘉吉公司 | 用于产生甜菊醇糖苷的发酵方法 |
| CN105255971B (zh) * | 2015-10-27 | 2018-10-23 | 江南大学 | 双酶法制备甜菊单糖苷 |
| SG11201803918VA (en) * | 2015-12-10 | 2018-06-28 | Evolva Sa | Production of steviol glycosides in recombinant hosts |
| WO2017204284A1 (ja) * | 2016-05-25 | 2017-11-30 | サントリーホールディングス株式会社 | Ａｏｂｇｌ１１ホモログを用いたステビオールおよびステビオール配糖体の製造方法 |
| RU2019114181A (ru) | 2016-10-14 | 2020-11-16 | Конаджен Инк. | Биосинтетическое получение стевиоловых гликозидов и связанные с этим способы |
| EP3592157A4 (en) | 2017-03-06 | 2021-01-13 | Conagen Inc. | BIOSYNTHETIC PRODUCTION OF STEVIOL GLYCOSIDE REBAUDIOSIDE D4 FROM REBAUDIOSIDE E |
| US20220042060A1 (en) | 2017-09-08 | 2022-02-10 | Conagen Inc. | Biosynthesis production of steviol glycosides and processes therefore |
-
2018
- 2018-06-29 MX MX2019015404A patent/MX2019015404A/es unknown
- 2018-06-29 MY MYPI2019007651A patent/MY204670A/en unknown
- 2018-06-29 CA CA3068440A patent/CA3068440A1/en active Pending
- 2018-06-29 CN CN201880044142.4A patent/CN110809408B/zh active Active
- 2018-06-29 WO PCT/US2018/040193 patent/WO2019006244A1/en not_active Ceased
- 2018-06-29 EP EP18823343.1A patent/EP3644758A4/en active Pending
- 2018-06-29 JP JP2019570910A patent/JP7116751B2/ja active Active
- 2018-06-29 BR BR112019027992-0A patent/BR112019027992B1/pt active IP Right Grant
- 2018-06-29 AU AU2018294258A patent/AU2018294258A1/en not_active Abandoned
- 2018-06-29 KR KR1020197038507A patent/KR102792406B1/ko active Active
-
2019
- 2019-12-23 US US16/725,242 patent/US11414689B2/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| BR112019027992A2 (pt) | 2020-07-07 |
| CA3068440A1 (en) | 2019-01-03 |
| KR20200024789A (ko) | 2020-03-09 |
| KR102792406B1 (ko) | 2025-04-08 |
| EP3644758A1 (en) | 2020-05-06 |
| JP7116751B2 (ja) | 2022-08-10 |
| CN110809408A (zh) | 2020-02-18 |
| BR112019027992B1 (pt) | 2024-02-27 |
| US20200291441A1 (en) | 2020-09-17 |
| WO2019006244A1 (en) | 2019-01-03 |
| JP2020526185A (ja) | 2020-08-31 |
| US11414689B2 (en) | 2022-08-16 |
| EP3644758A4 (en) | 2021-03-31 |
| AU2018294258A1 (en) | 2020-02-06 |
| MY204670A (en) | 2024-09-07 |
| RU2020102899A (ru) | 2021-07-30 |
| RU2020102899A3 (es) | 2021-11-09 |
| CN110809408B (zh) | 2024-09-10 |
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