CN111344399A - 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 - Google Patents
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 Download PDFInfo
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- CN111344399A CN111344399A CN201880037977.7A CN201880037977A CN111344399A CN 111344399 A CN111344399 A CN 111344399A CN 201880037977 A CN201880037977 A CN 201880037977A CN 111344399 A CN111344399 A CN 111344399A
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- udp
- glucosyltransferase
- rebaudioside
- mutant
- amino acid
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Links
- 101710204244 Processive diacylglycerol beta-glucosyltransferase Proteins 0.000 title claims abstract description 56
- 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 title claims abstract description 40
- 238000000034 method Methods 0.000 title claims abstract description 18
- 108090000623 proteins and genes Proteins 0.000 claims abstract description 17
- 239000002773 nucleotide Substances 0.000 claims abstract description 3
- 125000003729 nucleotide group Chemical group 0.000 claims abstract description 3
- 125000003275 alpha amino acid group Chemical group 0.000 claims description 22
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- 239000001512 FEMA 4601 Substances 0.000 claims description 15
- 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 15
- 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 15
- 235000019203 rebaudioside A Nutrition 0.000 claims description 15
- 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 15
- 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 description 14
- 238000006555 catalytic reaction Methods 0.000 claims description 10
- 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 9
- 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 claims description 9
- XCCTYIAWTASOJW-XVFCMESISA-N Uridine-5'-Diphosphate Chemical compound O[C@@H]1[C@H](O)[C@@H](COP(O)(=O)OP(O)(O)=O)O[C@H]1N1C(=O)NC(=O)C=C1 XCCTYIAWTASOJW-XVFCMESISA-N 0.000 claims description 8
- 230000035772 mutation Effects 0.000 claims description 8
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- 102000004169 proteins and genes Human genes 0.000 claims description 8
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- 108010043934 Sucrose synthase Proteins 0.000 claims description 6
- 241000219195 Arabidopsis thaliana Species 0.000 claims description 5
- 229930006000 Sucrose Natural products 0.000 claims description 5
- 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 5
- XCCTYIAWTASOJW-UHFFFAOYSA-N UDP-Glc Natural products OC1C(O)C(COP(O)(=O)OP(O)(O)=O)OC1N1C(=O)NC(=O)C=C1 XCCTYIAWTASOJW-UHFFFAOYSA-N 0.000 claims description 5
- 239000012620 biological material Substances 0.000 claims description 5
- 239000005720 sucrose Substances 0.000 claims description 5
- 102220583750 Cellular tumor antigen p53_A69D_mutation Human genes 0.000 claims description 4
- 230000002255 enzymatic effect Effects 0.000 claims description 4
- 244000005700 microbiome Species 0.000 claims description 3
- 150000001413 amino acids Chemical group 0.000 claims description 2
- 229920001184 polypeptide Polymers 0.000 claims description 2
- 102000004196 processed proteins & peptides Human genes 0.000 claims description 2
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 2
- 239000004383 Steviol glycoside Substances 0.000 claims 2
- 229930182488 steviol glycoside Natural products 0.000 claims 2
- 235000019411 steviol glycoside Nutrition 0.000 claims 2
- 150000008144 steviol glycosides Chemical class 0.000 claims 2
- 102000004190 Enzymes Human genes 0.000 abstract description 24
- 108090000790 Enzymes Proteins 0.000 abstract description 24
- 230000000694 effects Effects 0.000 abstract description 10
- 238000002741 site-directed mutagenesis Methods 0.000 abstract description 3
- 238000012408 PCR amplification Methods 0.000 description 7
- 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 5
- 239000007788 liquid Substances 0.000 description 5
- 229940013618 stevioside Drugs 0.000 description 5
- 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 5
- 239000013612 plasmid Substances 0.000 description 4
- 241000588724 Escherichia coli Species 0.000 description 3
- 125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 241000196324 Embryophyta Species 0.000 description 2
- 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 description 2
- 108010055629 Glucosyltransferases Proteins 0.000 description 2
- 102000000340 Glucosyltransferases Human genes 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 239000000348 glycosyl donor Substances 0.000 description 2
- 239000001963 growth medium Substances 0.000 description 2
- 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 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000012216 screening Methods 0.000 description 2
- 238000012163 sequencing technique Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- 230000001131 transforming effect Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 229920002527 Glycogen Polymers 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000209094 Oryza Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 240000008467 Oryza sativa Japonica Group Species 0.000 description 1
- 235000005043 Oryza sativa Japonica Group Nutrition 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 241001052560 Thallis Species 0.000 description 1
- 239000000370 acceptor Substances 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
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- 238000005119 centrifugation Methods 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
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- 238000005520 cutting process Methods 0.000 description 1
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- 238000001514 detection method Methods 0.000 description 1
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- 239000000386 donor Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000006911 enzymatic reaction Methods 0.000 description 1
- 238000001952 enzyme assay Methods 0.000 description 1
- 238000001976 enzyme digestion Methods 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 229940096919 glycogen Drugs 0.000 description 1
- 239000000937 glycosyl acceptor Substances 0.000 description 1
- 125000003147 glycosyl group Chemical group 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 238000007852 inverse PCR Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 235000021096 natural sweeteners Nutrition 0.000 description 1
- 229920001542 oligosaccharide Polymers 0.000 description 1
- 150000002482 oligosaccharides Chemical class 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
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- 235000009566 rice Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
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- 239000007858 starting material Substances 0.000 description 1
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- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 150000003722 vitamin derivatives Chemical class 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
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- C12N15/00—Mutation or genetic engineering; DNA or RNA concerning genetic engineering, vectors, e.g. plasmids, or their isolation, preparation or purification; Use of hosts therefor
- C12N15/09—Recombinant DNA-technology
- C12N15/63—Introduction of foreign genetic material using vectors; Vectors; Use of hosts therefor; Regulation of expression
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- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
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- C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
- C12N9/10—Transferases (2.)
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- 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
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- Biotechnology (AREA)
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- General Chemical & Material Sciences (AREA)
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- Enzymes And Modification Thereof (AREA)
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Abstract
提供了一种UDP‑葡萄糖基转移酶突变体、其应用及制备莱鲍迪苷D的方法，对野生型UDP‑葡萄糖基转移酶的基因序列进行定点突变，获得了包括SEQ ID NO：3在内的一系列突变体，这些突变体的酶活力和pH稳定性较野生型亲本得到提高。
Description
PCT国内申请，说明书已公开。
Claims (10)
- PCT国内申请，权利要求书已公开。
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/CN2018/115937 WO2020097922A1 (zh) | 2018-11-16 | 2018-11-16 | 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 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN111344399A true CN111344399A (zh) | 2020-06-26 |
| CN111344399B CN111344399B (zh) | 2023-03-03 |
Family
ID=70730387
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201880037977.7A Active CN111344399B (zh) | 2018-11-16 | 2018-11-16 | 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 |
Country Status (2)
| Country | Link |
|---|---|
| CN (1) | CN111344399B (zh) |
| WO (1) | WO2020097922A1 (zh) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2022253282A1 (zh) * | 2021-06-01 | 2022-12-08 | 弈柯莱生物科技(上海)股份有限公司 | 一种糖基转移酶及其应用 |
| WO2022257983A1 (zh) * | 2021-06-08 | 2022-12-15 | 弈柯莱生物科技(上海)股份有限公司 | 一种β-1,2-糖基转移酶及其应用 |
| WO2022262630A1 (zh) * | 2021-06-16 | 2022-12-22 | 弈柯莱生物科技(上海)股份有限公司 | 一种糖基转移酶及其应用 |
| WO2023005779A1 (zh) * | 2021-07-27 | 2023-02-02 | 弈柯莱生物科技(上海)股份有限公司 | 一种蔗糖合成酶及其应用 |
| CN117431229A (zh) * | 2023-11-03 | 2024-01-23 | 铭诚惠众(江苏)药物研究有限公司 | 一种糖基转移酶ugt91c1突变体及其应用 |
| CN117431229B (zh) * | 2023-11-03 | 2024-07-09 | 铭诚惠众(江苏)药物研究有限公司 | 一种糖基转移酶ugt91c1突变体及其应用 |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN116218806B (zh) * | 2022-10-21 | 2024-05-10 | 山东大学 | 一种N-糖基转移酶突变体AaFQ及其应用 |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101942424A (zh) * | 2010-08-24 | 2011-01-12 | 北京农学院 | Udp-葡萄糖基转移酶突变体的编码基因及其应用 |
| US20150315623A1 (en) * | 2014-05-05 | 2015-11-05 | Conagen Inc. | Non-caloric sweetener |
| CN105164270A (zh) * | 2013-02-28 | 2015-12-16 | Cj第一制糖株式会社 | 由甜菊苷制备莱苞迪甙a的方法 |
| CN107109453A (zh) * | 2014-11-05 | 2017-08-29 | 马努斯生物合成股份有限公司 | 甜菊醇糖苷的微生物产生 |
-
2018
- 2018-11-16 WO PCT/CN2018/115937 patent/WO2020097922A1/zh active Application Filing
- 2018-11-16 CN CN201880037977.7A patent/CN111344399B/zh active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101942424A (zh) * | 2010-08-24 | 2011-01-12 | 北京农学院 | Udp-葡萄糖基转移酶突变体的编码基因及其应用 |
| CN105164270A (zh) * | 2013-02-28 | 2015-12-16 | Cj第一制糖株式会社 | 由甜菊苷制备莱苞迪甙a的方法 |
| US20150315623A1 (en) * | 2014-05-05 | 2015-11-05 | Conagen Inc. | Non-caloric sweetener |
| CN107109453A (zh) * | 2014-11-05 | 2017-08-29 | 马努斯生物合成股份有限公司 | 甜菊醇糖苷的微生物产生 |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2022253282A1 (zh) * | 2021-06-01 | 2022-12-08 | 弈柯莱生物科技(上海)股份有限公司 | 一种糖基转移酶及其应用 |
| WO2022257983A1 (zh) * | 2021-06-08 | 2022-12-15 | 弈柯莱生物科技(上海)股份有限公司 | 一种β-1,2-糖基转移酶及其应用 |
| WO2022262630A1 (zh) * | 2021-06-16 | 2022-12-22 | 弈柯莱生物科技(上海)股份有限公司 | 一种糖基转移酶及其应用 |
| WO2023005779A1 (zh) * | 2021-07-27 | 2023-02-02 | 弈柯莱生物科技(上海)股份有限公司 | 一种蔗糖合成酶及其应用 |
| CN117431229A (zh) * | 2023-11-03 | 2024-01-23 | 铭诚惠众(江苏)药物研究有限公司 | 一种糖基转移酶ugt91c1突变体及其应用 |
| CN117431229B (zh) * | 2023-11-03 | 2024-07-09 | 铭诚惠众(江苏)药物研究有限公司 | 一种糖基转移酶ugt91c1突变体及其应用 |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2020097922A1 (zh) | 2020-05-22 |
| CN111344399B (zh) | 2023-03-03 |
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