JP2019536444A5 - - Google Patents
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- Publication number
- JP2019536444A5 JP2019536444A5 JP2019521072A JP2019521072A JP2019536444A5 JP 2019536444 A5 JP2019536444 A5 JP 2019536444A5 JP 2019521072 A JP2019521072 A JP 2019521072A JP 2019521072 A JP2019521072 A JP 2019521072A JP 2019536444 A5 JP2019536444 A5 JP 2019536444A5
- Authority
- JP
- Japan
- Prior art keywords
- rebaudioside
- glycosyltransferase
- udp
- ugt
- donor
- 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.)
- Granted
Links
- 238000000034 method Methods 0.000 claims description 30
- 238000006243 chemical reaction Methods 0.000 claims description 22
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 14
- HINSNOJRHFIMKB-DJDMUFINSA-N [(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl] (1R,4S,5R,9S,10R,13S)-13-[(2S,3R,4S,5R,6R)-5-hydroxy-6-(hydroxymethyl)-3,4-bis[[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy]oxan-2-yl]oxy-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.01,10.04,9]hexadecane-5-carboxylate Chemical compound [H][C@@]1(O[C@@H]2[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]2OC(=O)[C@]2(C)CCC[C@@]3(C)[C@]4([H])CC[C@@]5(C[C@]4(CC5=C)CC[C@]23[H])O[C@]2([H])O[C@H](CO)[C@@H](O)[C@H](O[C@]3([H])O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)[C@H]2O[C@]2([H])O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)O[C@@H](C)[C@H](O)[C@@H](O)[C@H]1O HINSNOJRHFIMKB-DJDMUFINSA-N 0.000 claims description 13
- 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 claims description 8
- 239000001512 FEMA 4601 Substances 0.000 claims description 7
- 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 7
- 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 7
- 235000019203 rebaudioside A Nutrition 0.000 claims description 7
- 241000588724 Escherichia coli Species 0.000 claims description 6
- 240000007594 Oryza sativa Species 0.000 claims description 6
- 235000007164 Oryza sativa Nutrition 0.000 claims description 6
- 125000003275 alpha amino acid group Chemical group 0.000 claims description 5
- 238000002955 isolation Methods 0.000 claims description 5
- 239000008363 phosphate buffer Substances 0.000 claims description 5
- 239000011347 resin Substances 0.000 claims description 5
- 229920005989 resin Polymers 0.000 claims description 5
- 239000000386 donor Substances 0.000 claims description 4
- 238000006911 enzymatic reaction Methods 0.000 claims description 4
- 241000235058 Komagataella pastoris Species 0.000 claims description 3
- 239000000348 glycosyl donor Substances 0.000 claims description 3
- 240000004808 Saccharomyces cerevisiae Species 0.000 claims description 2
- 235000014680 Saccharomyces cerevisiae Nutrition 0.000 claims description 2
- 230000000813 microbial effect Effects 0.000 claims description 2
- 244000005700 microbiome Species 0.000 claims description 2
- 239000008346 aqueous phase Substances 0.000 claims 2
- 241000235343 Saccharomycetales Species 0.000 claims 1
- 125000003147 glycosyl group Chemical group 0.000 claims 1
- 239000006228 supernatant Substances 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000008176 lyophilized powder Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 244000228451 Stevia rebaudiana Species 0.000 description 3
- 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 description 3
- 235000013305 food Nutrition 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 229940013618 stevioside Drugs 0.000 description 3
- 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 description 3
- 235000019202 steviosides Nutrition 0.000 description 3
- SHZGCJCMOBCMKK-UHFFFAOYSA-N D-mannomethylose Natural products CC1OC(O)C(O)C(O)C1O SHZGCJCMOBCMKK-UHFFFAOYSA-N 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 2
- SHZGCJCMOBCMKK-JFNONXLTSA-N L-rhamnopyranose Chemical compound C[C@@H]1OC(O)[C@H](O)[C@H](O)[C@H]1O SHZGCJCMOBCMKK-JFNONXLTSA-N 0.000 description 2
- PNNNRSAQSRJVSB-UHFFFAOYSA-N L-rhamnose Natural products CC(O)C(O)C(O)C(O)C=O PNNNRSAQSRJVSB-UHFFFAOYSA-N 0.000 description 2
- 229930006000 Sucrose Natural products 0.000 description 2
- 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 description 2
- 235000013361 beverage Nutrition 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 235000003599 food sweetener Nutrition 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 235000021096 natural sweeteners Nutrition 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 239000005720 sucrose Substances 0.000 description 2
- 239000003765 sweetening agent Substances 0.000 description 2
- 108010011485 Aspartame Proteins 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 102000003960 Ligases Human genes 0.000 description 1
- 108090000364 Ligases Proteins 0.000 description 1
- 235000006092 Stevia rebaudiana Nutrition 0.000 description 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 description 1
- 239000008122 artificial sweetener Substances 0.000 description 1
- 235000021311 artificial sweeteners Nutrition 0.000 description 1
- 239000000605 aspartame Substances 0.000 description 1
- IAOZJIPTCAWIRG-QWRGUYRKSA-N aspartame Chemical compound OC(=O)C[C@H](N)C(=O)N[C@H](C(=O)OC)CC1=CC=CC=C1 IAOZJIPTCAWIRG-QWRGUYRKSA-N 0.000 description 1
- 235000010357 aspartame Nutrition 0.000 description 1
- 229960003438 aspartame Drugs 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 235000013373 food additive Nutrition 0.000 description 1
- 239000002778 food additive Substances 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 235000019534 high fructose corn syrup Nutrition 0.000 description 1
- 235000012907 honey Nutrition 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- BPHPUYQFMNQIOC-NXRLNHOXSA-N isopropyl beta-D-thiogalactopyranoside Chemical compound CC(C)S[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O BPHPUYQFMNQIOC-NXRLNHOXSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 229930188195 rebaudioside Natural products 0.000 description 1
- 108091008146 restriction endonucleases Proteins 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/CN2016/102942 WO2018072211A1 (zh) | 2016-10-21 | 2016-10-21 | 一种酶法制备瑞鲍迪甙j的方法 |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2021024483A Division JP7210626B2 (ja) | 2021-02-18 | 2021-02-18 | 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 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2019536444A JP2019536444A (ja) | 2019-12-19 |
| JP2019536444A5 true JP2019536444A5 (enExample) | 2021-01-14 |
| JP6842800B2 JP6842800B2 (ja) | 2021-03-17 |
Family
ID=62018306
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2019521072A Active JP6842800B2 (ja) | 2016-10-21 | 2016-10-21 | 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 |
Country Status (9)
| Country | Link |
|---|---|
| US (3) | US11359222B2 (enExample) |
| EP (1) | EP3543346A4 (enExample) |
| JP (1) | JP6842800B2 (enExample) |
| CN (2) | CN110177881B (enExample) |
| AU (1) | AU2016427128C1 (enExample) |
| CA (1) | CA3041147A1 (enExample) |
| MX (1) | MX2019004630A (enExample) |
| RU (1) | RU2736352C1 (enExample) |
| WO (1) | WO2018072211A1 (enExample) |
Families Citing this family (3)
| 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 |
| EP3530746A4 (en) | 2016-10-21 | 2020-06-24 | Pepsico, Inc. | METHOD FOR PRODUCING REBAUDIOSIDE C BY ENZYMATIC METHOD |
| 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 |
Family Cites Families (29)
| 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 | |
| ES2661539T3 (es) * | 2009-10-15 | 2018-04-02 | Purecircle Sdn Bhd | Rebaudiósido D de pureza elevada y aplicaciones |
| BR122021005297B1 (pt) | 2010-06-02 | 2022-02-22 | Evolva, Inc | Método para transferir uma segunda porção de açúcar para uma posição c-2' de uma glicose em um glicosídeo de esteviol |
| US8962698B2 (en) | 2011-01-28 | 2015-02-24 | Tate & Lyle Ingredients Americas Llc | Rebaudioside-mogroside V blends |
| JP6262653B2 (ja) * | 2011-08-08 | 2018-01-17 | エヴォルヴァ エスアー．Ｅｖｏｌｖａ Ｓａ． | ステビオール配糖体の組換え生産 |
| 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 |
| CN103159808B (zh) | 2011-12-09 | 2017-03-29 | 上海泓博智源医药股份有限公司 | 一种制备天然甜味剂的工艺方法 |
| 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 |
| EP2852296B1 (en) * | 2012-05-22 | 2021-12-15 | PureCircle SDN BHD | Process for producing a high-purity steviol glycoside |
| US9752174B2 (en) | 2013-05-28 | 2017-09-05 | Purecircle Sdn Bhd | High-purity steviol glycosides |
| 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 |
| KR20150115002A (ko) | 2013-02-06 | 2015-10-13 | 에볼바 에스아 | 레바우디오시드 ｄ 및 레바우디오시드 ｍ의 개선된 생산 방법 |
| US9717267B2 (en) * | 2013-03-14 | 2017-08-01 | The Coca-Cola Company | Beverages containing rare sugars |
| 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 |
| US9522929B2 (en) | 2014-05-05 | 2016-12-20 | Conagen Inc. | Non-caloric sweetener |
| EP3183349B1 (en) | 2014-08-19 | 2020-03-25 | Purecircle SDN BHD | Method for preparing rebaudioside i |
| AU2015327940B2 (en) * | 2014-10-03 | 2020-04-16 | Conagen Inc. | Non-caloric sweeteners and methods for synthesizing |
| 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 |
| EP3530746A4 (en) | 2016-10-21 | 2020-06-24 | Pepsico, Inc. | METHOD FOR PRODUCING REBAUDIOSIDE C BY ENZYMATIC METHOD |
-
2016
- 2016-10-21 JP JP2019521072A patent/JP6842800B2/ja active Active
- 2016-10-21 WO PCT/CN2016/102942 patent/WO2018072211A1/zh not_active Ceased
- 2016-10-21 CN CN201680089970.0A patent/CN110177881B/zh active Active
- 2016-10-21 EP EP16919379.4A patent/EP3543346A4/en active Pending
- 2016-10-21 RU RU2019112426A patent/RU2736352C1/ru active
- 2016-10-21 MX MX2019004630A patent/MX2019004630A/es unknown
- 2016-10-21 US US16/343,340 patent/US11359222B2/en active Active
- 2016-10-21 CA CA3041147A patent/CA3041147A1/en active Pending
- 2016-10-21 AU AU2016427128A patent/AU2016427128C1/en active Active
- 2016-10-21 CN CN202310493375.5A patent/CN116574775A/zh active Pending
-
2022
- 2022-06-06 US US17/805,626 patent/US11952604B2/en active Active
-
2024
- 2024-03-08 US US18/600,332 patent/US20240287567A1/en not_active Abandoned
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