JP2019532650A5 - - Google Patents
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- JP2019532650A5 JP2019532650A5 JP2019521117A JP2019521117A JP2019532650A5 JP 2019532650 A5 JP2019532650 A5 JP 2019532650A5 JP 2019521117 A JP2019521117 A JP 2019521117A JP 2019521117 A JP2019521117 A JP 2019521117A JP 2019532650 A5 JP2019532650 A5 JP 2019532650A5
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- 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 claims description 52
- 238000000034 method Methods 0.000 claims description 49
- 238000006243 chemical reaction Methods 0.000 claims description 36
- 239000001776 FEMA 4720 Substances 0.000 claims description 26
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 22
- 125000003275 alpha amino acid group Chemical group 0.000 claims description 17
- 244000228451 Stevia rebaudiana Species 0.000 claims description 10
- 235000006092 Stevia rebaudiana Nutrition 0.000 claims description 9
- 108700023372 Glycosyltransferases Proteins 0.000 claims description 8
- 102000051366 Glycosyltransferases Human genes 0.000 claims description 8
- 241000588724 Escherichia coli Species 0.000 claims description 7
- 229930006000 Sucrose Natural products 0.000 claims description 6
- 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 description 6
- 239000000348 glycosyl donor Substances 0.000 claims description 6
- 239000005720 sucrose Substances 0.000 claims description 6
- 238000006911 enzymatic reaction Methods 0.000 claims description 5
- 244000005700 microbiome Species 0.000 claims description 4
- 102000035195 Peptidases Human genes 0.000 claims description 3
- 108091005804 Peptidases Proteins 0.000 claims description 3
- 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 description 3
- 235000019833 protease Nutrition 0.000 claims description 3
- SHZGCJCMOBCMKK-UHFFFAOYSA-N D-mannomethylose Natural products CC1OC(O)C(O)C(O)C1O SHZGCJCMOBCMKK-UHFFFAOYSA-N 0.000 claims description 2
- 108090000790 Enzymes Proteins 0.000 claims description 2
- 102000004190 Enzymes Human genes 0.000 claims description 2
- PNNNRSAQSRJVSB-UHFFFAOYSA-N L-rhamnose Natural products CC(O)C(O)C(O)C(O)C=O PNNNRSAQSRJVSB-UHFFFAOYSA-N 0.000 claims description 2
- 240000007594 Oryza sativa Species 0.000 claims description 2
- 235000007164 Oryza sativa Nutrition 0.000 claims description 2
- 108010043934 Sucrose synthase Proteins 0.000 claims description 2
- 229930182478 glucoside Natural products 0.000 claims description 2
- 150000008131 glucosides Chemical class 0.000 claims description 2
- 230000000813 microbial effect Effects 0.000 claims description 2
- 239000008055 phosphate buffer solution Substances 0.000 claims description 2
- 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
- 241000235058 Komagataella pastoris Species 0.000 claims 1
- 241000235343 Saccharomycetales Species 0.000 claims 1
- 239000008103 glucose Substances 0.000 claims 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- 239000012634 fragment Substances 0.000 description 8
- 239000000758 substrate Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 7
- 239000006228 supernatant Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 108091008146 restriction endonucleases Proteins 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- YWPVROCHNBYFTP-UHFFFAOYSA-N Rubusoside 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)C1O YWPVROCHNBYFTP-UHFFFAOYSA-N 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 239000002609 medium Substances 0.000 description 5
- 239000008363 phosphate buffer Substances 0.000 description 5
- YWPVROCHNBYFTP-OSHKXICASA-N rubusoside Chemical group 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 YWPVROCHNBYFTP-OSHKXICASA-N 0.000 description 5
- 238000005119 centrifugation Methods 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 238000001514 detection method Methods 0.000 description 4
- 239000000386 donor Substances 0.000 description 4
- 238000001976 enzyme digestion Methods 0.000 description 4
- 235000013305 food Nutrition 0.000 description 4
- 239000008176 lyophilized powder Substances 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 101710204244 Processive diacylglycerol beta-glucosyltransferase Proteins 0.000 description 3
- 235000013361 beverage Nutrition 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 230000006698 induction Effects 0.000 description 3
- 238000011081 inoculation Methods 0.000 description 3
- 108090000623 proteins and genes Proteins 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- 102000003960 Ligases Human genes 0.000 description 2
- 108090000364 Ligases Proteins 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 235000003599 food sweetener Nutrition 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 239000012528 membrane 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
- 239000002994 raw material Substances 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000003765 sweetening agent Substances 0.000 description 2
- 125000003944 tolyl group Chemical group 0.000 description 2
- 101000630755 Arabidopsis thaliana Sucrose synthase 1 Proteins 0.000 description 1
- 108010011485 Aspartame Proteins 0.000 description 1
- 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 description 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 description 1
- 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 1
- 241000235648 Pichia Species 0.000 description 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 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- 235000014680 Saccharomyces cerevisiae Nutrition 0.000 description 1
- 241000544066 Stevia Species 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
- 239000007864 aqueous solution Substances 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
- 235000009508 confectionery Nutrition 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 235000013373 food additive Nutrition 0.000 description 1
- 239000002778 food additive Substances 0.000 description 1
- 238000010353 genetic engineering Methods 0.000 description 1
- 108700014210 glycosyltransferase activity proteins Proteins 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 235000019534 high fructose corn syrup Nutrition 0.000 description 1
- 235000012907 honey Nutrition 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000010369 molecular cloning Methods 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 229930188195 rebaudioside Natural products 0.000 description 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 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 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
- 235000019202 steviosides Nutrition 0.000 description 1
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 (2)
| Publication Number | Publication Date |
|---|---|
| JP2019532650A JP2019532650A (ja) | 2019-11-14 |
| JP2019532650A5 true JP2019532650A5 (enExample) | 2020-11-26 |
Family
ID=62018093
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2019521117A Withdrawn JP2019532650A (ja) | 2016-10-21 | 2016-10-21 | 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 |
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 |
Family Cites Families (27)
| 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 |
| 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 |
| 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 |
| 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 |
| 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
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