CN103627756A - Method for enzymatic synthesis of isoquercitrin by using continuous-flow tubular microreactor - Google Patents
Method for enzymatic synthesis of isoquercitrin by using continuous-flow tubular microreactor Download PDFInfo
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- isoquercitrin
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- rutin
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- OVSQVDMCBVZWGM-QSOFNFLRSA-N quercetin 3-O-beta-D-glucopyranoside Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=C(C=2C=C(O)C(O)=CC=2)OC2=CC(O)=CC(O)=C2C1=O OVSQVDMCBVZWGM-QSOFNFLRSA-N 0.000 title claims abstract description 40
- OVSQVDMCBVZWGM-IDRAQACASA-N Hirsutrin Natural products O([C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1)C1=C(c2cc(O)c(O)cc2)Oc2c(c(O)cc(O)c2)C1=O OVSQVDMCBVZWGM-IDRAQACASA-N 0.000 title claims abstract description 39
- FVQOMEDMFUMIMO-UHFFFAOYSA-N Hyperosid Natural products OC1C(O)C(O)C(CO)OC1OC1C(=O)C2=C(O)C=C(O)C=C2OC1C1=CC=C(O)C(O)=C1 FVQOMEDMFUMIMO-UHFFFAOYSA-N 0.000 title claims abstract description 39
- GXMWXESSGGEWEM-UHFFFAOYSA-N isoquercitrin Natural products OCC(O)C1OC(OC2C(Oc3cc(O)cc(O)c3C2=O)c4ccc(O)c(O)c4)C(O)C1O GXMWXESSGGEWEM-UHFFFAOYSA-N 0.000 title claims abstract description 39
- 238000000034 method Methods 0.000 title claims abstract description 26
- 230000002255 enzymatic effect Effects 0.000 title claims abstract description 21
- 230000015572 biosynthetic process Effects 0.000 title abstract 2
- 238000003786 synthesis reaction Methods 0.000 title abstract 2
- 238000006243 chemical reaction Methods 0.000 claims abstract description 35
- JMGZEFIQIZZSBH-UHFFFAOYSA-N Bioquercetin Natural products CC1OC(OCC(O)C2OC(OC3=C(Oc4cc(O)cc(O)c4C3=O)c5ccc(O)c(O)c5)C(O)C2O)C(O)C(O)C1O JMGZEFIQIZZSBH-UHFFFAOYSA-N 0.000 claims abstract description 29
- IVTMALDHFAHOGL-UHFFFAOYSA-N eriodictyol 7-O-rutinoside Natural products OC1C(O)C(O)C(C)OC1OCC1C(O)C(O)C(O)C(OC=2C=C3C(C(C(O)=C(O3)C=3C=C(O)C(O)=CC=3)=O)=C(O)C=2)O1 IVTMALDHFAHOGL-UHFFFAOYSA-N 0.000 claims abstract description 29
- FDRQPMVGJOQVTL-UHFFFAOYSA-N quercetin rutinoside Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC=2C(C3=C(O)C=C(O)C=C3OC=2C=2C=C(O)C(O)=CC=2)=O)O1 FDRQPMVGJOQVTL-UHFFFAOYSA-N 0.000 claims abstract description 29
- IKGXIBQEEMLURG-BKUODXTLSA-N rutin Chemical compound O[C@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@@H]1OC[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](OC=2C(C3=C(O)C=C(O)C=C3OC=2C=2C=C(O)C(O)=CC=2)=O)O1 IKGXIBQEEMLURG-BKUODXTLSA-N 0.000 claims abstract description 29
- ALABRVAAKCSLSC-UHFFFAOYSA-N rutin Natural products CC1OC(OCC2OC(O)C(O)C(O)C2O)C(O)C(O)C1OC3=C(Oc4cc(O)cc(O)c4C3=O)c5ccc(O)c(O)c5 ALABRVAAKCSLSC-UHFFFAOYSA-N 0.000 claims abstract description 29
- 235000005493 rutin Nutrition 0.000 claims abstract description 29
- 229960004555 rutoside Drugs 0.000 claims abstract description 29
- 239000000243 solution Substances 0.000 claims abstract description 24
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- 108010030923 hesperidinase Proteins 0.000 claims abstract description 11
- 239000012153 distilled water Substances 0.000 claims abstract description 10
- 239000007788 liquid Substances 0.000 claims abstract description 7
- 238000006911 enzymatic reaction Methods 0.000 claims abstract description 4
- IQQRAVYLUAZUGX-UHFFFAOYSA-N 1-butyl-3-methylimidazolium Chemical compound CCCCN1C=C[N+](C)=C1 IQQRAVYLUAZUGX-UHFFFAOYSA-N 0.000 claims abstract description 3
- CIJQGPVMMRXSQW-UHFFFAOYSA-M sodium;2-aminoacetic acid;hydroxide Chemical compound O.[Na+].NCC([O-])=O CIJQGPVMMRXSQW-UHFFFAOYSA-M 0.000 claims abstract description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 3
- 239000012452 mother liquor Substances 0.000 claims description 18
- 239000000463 material Substances 0.000 claims description 16
- 238000002347 injection Methods 0.000 claims description 7
- 239000007924 injection Substances 0.000 claims description 7
- 238000001746 injection moulding Methods 0.000 claims description 6
- 239000004205 dimethyl polysiloxane Substances 0.000 claims description 5
- 238000005530 etching Methods 0.000 claims description 5
- 239000011521 glass Substances 0.000 claims description 5
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 claims description 5
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- 150000001875 compounds Chemical class 0.000 claims description 2
- 235000013870 dimethyl polysiloxane Nutrition 0.000 claims 1
- CXQXSVUQTKDNFP-UHFFFAOYSA-N octamethyltrisiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)O[Si](C)(C)C CXQXSVUQTKDNFP-UHFFFAOYSA-N 0.000 claims 1
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- -1 flavone compounds Chemical class 0.000 description 10
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- WUWHFEHKUQVYLF-UHFFFAOYSA-M sodium;2-aminoacetate Chemical compound [Na+].NCC([O-])=O WUWHFEHKUQVYLF-UHFFFAOYSA-M 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 6
- REFJWTPEDVJJIY-UHFFFAOYSA-N Quercetin Chemical compound C=1C(O)=CC(O)=C(C(C=2O)=O)C=1OC=2C1=CC=C(O)C(O)=C1 REFJWTPEDVJJIY-UHFFFAOYSA-N 0.000 description 4
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- ZVOLCUVKHLEPEV-UHFFFAOYSA-N Quercetagetin Natural products C1=C(O)C(O)=CC=C1C1=C(O)C(=O)C2=C(O)C(O)=C(O)C=C2O1 ZVOLCUVKHLEPEV-UHFFFAOYSA-N 0.000 description 2
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- SHZGCJCMOBCMKK-UHFFFAOYSA-N D-mannomethylose Natural products CC1OC(O)C(O)C(O)C1O SHZGCJCMOBCMKK-UHFFFAOYSA-N 0.000 description 1
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- GAMYVSCDDLXAQW-AOIWZFSPSA-N Thermopsosid Natural products O(C)c1c(O)ccc(C=2Oc3c(c(O)cc(O[C@H]4[C@H](O)[C@@H](O)[C@H](O)[C@H](CO)O4)c3)C(=O)C=2)c1 GAMYVSCDDLXAQW-AOIWZFSPSA-N 0.000 description 1
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- Saccharide Compounds (AREA)
Abstract
The invention relates to a method for the enzymatic synthesis of isoquercitrin by using a continuous-flow tubular microreactor. The method comprises the steps of preparing 0.01-5g/L rutin mother liquid in a manner of taking pH9 glycine-NaOH as a buffer solution by adopting the continuous-flow tubular microreactor with a micron-scale inside diameter, proportioning distilled water for enzyme according to the concentration of 0.001-0.1g/mL in a manner of taking hesperidinase as a catalyst, adding ionic liquid [Bmim][BF4] into a reaction system, proportioning the rutin mother liquid, enzyme liquid and the ionic liquid according to the volume ratio of 72: 18: 10, pumping a reaction solution into the microreactor by micro-injection pumps at the flow velocity of 0.1-100 microliter per minute, so as to be subjected to enzymatic reaction, and controlling the temperature to be 20-60 DEG C. The method is a time-saving efficient biocatalysis (biotransformation) method and is beneficial to the large-scale preparation of isoquercitrin.
Description
Technical field
The present invention relates to biochemical pharmacy field, be specifically related to a kind of method of utilizing the synthetic isoquercitrin of continuous current micro-reactor enzymatic.
Background technology
Isoquercitrin is a kind of bioactive natural flavone compounds such as antitumor, anti-oxidant and hypoglycemic that have, synthetic intermediate (the Food Chem. of food colorant (Enzymatically modified isoquercitrin) EMIQ, 2009,116 (1): 214-219).Isoquercitrin can extract from the plants such as mulberry leaf, Japnanese St. John's wort Herb, carry out the separated isoquercitrin that obtains, but in natural product, isoquercitrin content is extremely low, cannot meet the need of market as CN102827220A discloses from lotus leaf with column chromatography far away.In addition, isoquercitrin can be prepared by chemical method, as CN1817876A disclose a kind of in autoclave heating hydrolysis rutin prepare isoquercitrin, but in product, isoquercitrin and Quercetin coexist, wherein the highest yield of isoquercitrin only has 13%, and major part is Quercetin.Therefore, consider extraction method and chemical method high cost, in recent years enzymatic selective hydrolysis rutin to prepare isoquercitrin be generally acknowledged effective way.
Take cheap rutin as substrate, its rhamnosyl glycosidic bond is carried out to enzyme process selective hydrolysis and obtain isoquercitrin, for the production of isoquercitrin provides new thinking.As isoquercitrin is produced in the use rhamnoside enzyme catalysis rutin hydrolysis such as Petr, reaction 25h transformation efficiency can reach 93% (Bioresour.Technol., 2011,115 (0): 222-227).But it is lower that this hydrolytic process enzyme is cut efficiency, long reaction time, the expensive and recycling degree of enzyme is low, and this has all limited the production efficiency of isoquercitrin.Wang etc. are in novel ionic liquid cosolvent reaction system, with hesperidinase hydrolyzing rutin, produce isoquercitrin, reaction 10h transformation efficiency just can reach 93.4% (Bioresour.Technol., 2013,128,156-163), the method shortens dramatically on the reaction times with respect to traditional method, but still needs to be further improved.Therefore, be badly in need of finding a kind of isoquercitrin new technology more efficiently of preparing on this catalysis new system basis.
Since the mid-90 in 20th century, microreactor technology was risen, because its unique characteristic and advantage become rapidly study hotspot, in biocatalysis field, obtained increasing application.Continuous Flow tubular microreactors (Continuous-flow microreactor) is a kind of pipeline reactor of continuous flow, and the order of size of its reaction compartment is generally even nanometer of micron.Compare with popular response device, it is large that Continuous Flow tubular microreactors has surface-area, mass transfer, heat transfer efficiency be high, be convenient to the advantages such as amplification (Lab Chip., 2012,12,4080-4084).Du etc. have studied and in microreactor, have used the synthetic of lipase TLIM catalysis sugar ester, and it is fixed on lipase in the pipeline in 2mm.With traditional reactor comparison, its reaction 30min just can reach the yield of 90% left and right, while less side products (RSC Adv., 2012,2,2663-2665).Yet, there is not yet the method with the synthetic isoquercitrin of Continuous Flow tubular microreactors enzymically hydrolyse rutin.
Therefore, the present invention utilizes Continuous Flow tubular microreactors to come enzymically hydrolyse rutin to synthesize isoquercitrin first, be conducive to improve enzymatic reaction efficiency, Reaction time shorten, reduce power consumption, and simple to operate, be easy to the highly purified isoquercitrin of suitability for industrialized production, for promoting its tool in the industry such as makeup, medicine, food, be of great significance.
Summary of the invention
The technical problem solving: the invention provides a kind of method of utilizing the synthetic coffic acid propyl ester of Continuous Flow tubular microreactors enzymatic, to solve low, the consuming time length of speed of reaction of the synthetic isoquercitrin existing in prior art and to be difficult to the problems such as serialization production.
Technical scheme: the method for utilizing the synthetic isoquercitrin of tubular microreactors enzymatic of continuous flow, adopt the tubular microreactors of the continuous flow of micron level internal diameter, the rutin mother liquor that the glycine-NaOH of pH9 of take is 0.01～5g/L as damping fluid compound concentration, take hesperidinase as catalyzer, enzyme by concentration 0.001g/mL～0.1g/mL proportioning, adds ionic liquid [Bmim] [BF with distilled water in reaction system
4], rutin mother liquor, enzyme liquid and ionic liquid difference be 72:18:10 proportioning by volume, and the flow velocity with micro-injection pump with 0.1～100 μ L/min, pumps into reaction solution in microreactor and carries out enzymatic reaction, and temperature is controlled at 20-60 ℃.
Described tubular microreactors is provided with injection port, microchannel and the outlet connecting successively, the injection port end of reactor is connected with micro-injection pump, the outlet end of reactor is connected with collector, microchannel is serpentine channel, by hot injection moulding or etching method carves, the size internal diameter of passage is long 0.25m-2m, wide 100-500 μ m, dark 50 μ m, microreactor material is glass, PDMS (polydimethylsiloxane) or PMMA (Poly (methyl methacrylate)).
In described damping fluid, the concentration of rutin is preferably 0.1g/L.
Described enzyme liquid concentration is preferably as 0.1g/mL.
The described flow velocity with micro-injection pump is controlled is preferably 2 μ L/min.
Beneficial effect:
The present invention selects to utilize Continuous Flow tubular microreactors enzymatic to synthesize isoquercitrin, and the tradition reaction times is reduced to 30min by 10h, and yield can reach 100%, has greatly reduced power consumption, and reaction efficiency improves greatly; Production process becomes operate continuously from interval type operation, can continuous production.In addition, the apparatus structure of the present invention's employing is simple, only needs simply number to be amplified and gets final product expanding production capacity of equal proportion, has good industrial applications prospect, can meet the medicine industry needs that develop rapidly.
Accompanying drawing explanation
Fig. 1 is the tubular microreactors setting drawing of the synthetic isoquercitrin reaction formula of enzymatic of the present invention and continuous flow, 1 micro-injection pump, 2 microchannels, 3 collectors in figure;
Fig. 2 is the tubular microreactors of the continuous flow enlarged diagram that installs pipes, 4 injection ports, 2 microchannels, 5 outlets in figure.
Embodiment
Below in conjunction with specific embodiment, further set forth the present invention.Should be understood that these embodiment are only not used in and limit the scope of the invention for the present invention is described.In addition should be understood that those skilled in the art can make various changes or modifications the present invention after having read the content of the present invention's instruction, these equivalent form of values fall within the application's appended claims limited range equally.
Embodiment 1
The rutin mother liquor of the 5g/L that glycine-sodium hydrate buffer solution preparation pH of take is 9, the hesperidinase solution that the distilled water compound concentration of take is 0.001g/mL, rutin mother liquor, enzyme solution and ionic liquid [Bmin] [BF
4] respectively by volume for 72:18:10 is mixed with bioconversion reaction system.The reaction system preparing by micro-injection pump, is pumped in continuous flow reactor and is reacted with the flow velocity of 100 μ L/min.Tubular microreactors is provided with injection port 4, microchannel 2 and the outlet 5 connecting successively, the injection port end of reactor is connected with micro-injection pump 1, the outlet end of reactor is connected with collector 3, and this reactor is made a long snake pipe for 0.25m, wide 500 μ m, dark 50 μ m by PDMS-glass material by hot injection moulding.Temperature is controlled at 60 ℃, and reaction solution stops 36s in reactor.Collect outlet material, the yield that detects the synthetic isoquercitrin of enzymatic with HPLC is 2.3%.
The rutin mother liquor of the 0.01g/L that glycine-sodium hydrate buffer solution preparation pH of take is 9, the hesperidinase solution that the distilled water compound concentration of take is 0.1g/mL, rutin mother liquor, enzyme solution and ionic liquid [Bmin] [BF
4] respectively by volume for 72:18:10 is mixed with bioconversion reaction system.The reaction system preparing by micro-injection pump, is pumped in continuous flow reactor and is reacted with the flow velocity of 2 μ L/min.Apparatus structure is identical with embodiment 1, and this reactor cuts out a long snake pipe for 2m, wide 100 μ m, dark 50 μ m by PMMA material by etching method.Temperature is controlled at 20 ℃, and reaction solution stops 30min in reactor.Collect outlet material, the yield that detects the synthetic isoquercitrin of enzymatic with HPLC is 5.7%.
Embodiment 3
The rutin mother liquor of the 0.1g/L that glycine-sodium hydrate buffer solution preparation pH of take is 9, the hesperidinase solution that the distilled water compound concentration of take is 0.01g/mL, rutin mother liquor, enzyme solution and ionic liquid [Bmin] [BF
4] respectively by volume for 72:18:10 is mixed with bioconversion reaction system.The reaction system preparing by micro-injection pump, is pumped in continuous flow reactor and is reacted with the flow velocity of 20 μ L/min.Apparatus structure is identical with embodiment 1, and this reactor is made a long snake pipe for 1m, wide 100 μ m, dark 50 μ m by PDMS material by hot injection moulding.Temperature is controlled at 40 ℃, and reaction solution stops 15min in reactor.Collect outlet material, the yield that detects the synthetic isoquercitrin of enzymatic with HPLC is 58.6%.
The rutin mother liquor of the 0.1g/L that glycine-sodium hydrate buffer solution preparation pH of take is 9, the hesperidinase solution that the distilled water compound concentration of take is 0.05g/mL, rutin mother liquor, enzyme solution and ionic liquid [Bmin] [BF
4] respectively by volume for 72:18:10 is mixed with bioconversion reaction system.The reaction system preparing by micro-injection pump, is pumped in continuous flow reactor and is reacted with the flow velocity of 10 μ L/min.Apparatus structure is identical with embodiment 1, and this reactor cuts out a long snake pipe for 2m, wide 200 μ m, dark 50 μ m by PMMA material by etching method.Temperature is controlled at 40 ℃, and reaction solution stops 30min in reactor.Collect outlet material, the yield that detects the synthetic isoquercitrin of enzymatic with HPLC is 72.1%.
The rutin mother liquor of the 1g/L that glycine-sodium hydrate buffer solution preparation pH of take is 9, the hesperidinase solution that the distilled water compound concentration of take is 0.1g/mL, rutin mother liquor, enzyme solution and ionic liquid [Bmin] [BF
4] respectively by volume for 72:18:10 is mixed with bioconversion reaction system.The reaction system preparing by micro-injection pump, is pumped in continuous flow reactor and is reacted with the flow velocity of 4 μ L/min.Apparatus structure is identical with embodiment 1, and this reactor cuts out a long snake pipe for 1m, wide 200 μ m, dark 50 μ m by glass material by etching method.Temperature is controlled at 35 ℃, and reaction solution stops 15min in reactor.Collect outlet material, the yield that detects the synthetic isoquercitrin of enzymatic with HPLC is 89.1%.
Embodiment 6
The rutin mother liquor of the 0.5g/L that glycine-sodium hydrate buffer solution preparation pH of take is 9, the hesperidinase solution that the distilled water compound concentration of take is 0.1g/mL, rutin mother liquor, enzyme solution and ionic liquid [Bmin] [BF
4] respectively by volume for 72:18:10 is mixed with bioconversion reaction system.The reaction system preparing by micro-injection pump, is pumped in continuous flow reactor and is reacted with the flow velocity of 2 μ L/min.Apparatus structure is identical with embodiment 1, and this reactor cuts out a long snake pipe for 1m, wide 100 μ m, dark 50 μ m by PDMS material by hot injection moulding.Temperature is controlled at 35 ℃, and reaction solution stops 15min in reactor.Collect outlet material, the yield that detects the synthetic isoquercitrin of enzymatic with HPLC is 93.5%.
Embodiment 7
The rutin mother liquor of the 0.1g/L that glycine-sodium hydrate buffer solution preparation pH of take is 9, the hesperidinase solution that the distilled water compound concentration of take is 0.1g/mL, rutin mother liquor, enzyme solution and ionic liquid [Bmin] [BF
4] respectively by volume for 72:18:10 is mixed with bioconversion reaction system.The reaction system preparing by micro-injection pump, is pumped in continuous flow reactor and is reacted with the flow velocity of 2 μ L/min.Apparatus structure is identical with embodiment 1, and this reactor cuts out a long snake pipe for 2m, wide 200 μ m, dark 50 μ m by PDMS-glass material by hot injection moulding.Temperature is controlled at 40 ℃, and reaction solution stops 30min in reactor.Collect outlet material, the yield that detects the synthetic isoquercitrin of enzymatic with HPLC is 99.9%.
Claims (5)
1. utilize the method for the synthetic isoquercitrin of tubular microreactors enzymatic of continuous flow, it is characterized in that: the tubular microreactors that adopts the continuous flow of micron level internal diameter, the rutin mother liquor that the glycine-NaOH of pH9 of take is 0.01～5g/L as damping fluid compound concentration, take hesperidinase as catalyzer, enzyme by concentration 0.001g/mL～0.1g/mL proportioning, adds ionic liquid [Bmim] [BF with distilled water in reaction system
4], rutin mother liquor, enzyme liquid and ionic liquid difference be 72:18:10 proportioning by volume, and the flow velocity with micro-injection pump with 0.1～100 μ L/min, pumps into reaction solution in microreactor and carries out enzymatic reaction, and temperature is controlled at 20-60 ℃.
2. utilize according to claim 1 the method for the synthetic isoquercitrin of tubular microreactors enzymatic of continuous flow, it is characterized in that: described tubular microreactors is provided with the injection port (4) connecting successively, microchannel (2) and outlet (5), the injection port end of reactor is connected with micro-injection pump (1), the outlet end of reactor is connected with collector (3), microchannel is serpentine channel, by hot injection moulding or etching method carves, the size internal diameter of passage is long 0.25m-2m, wide 100-500 μ m, dark 50 μ m, microreactor material is glass, PDMS or PMMA.
3. the method for utilizing according to claim 1 the synthetic isoquercitrin of tubular microreactors enzymatic of continuous flow, is characterized in that: in described damping fluid, the concentration of rutin is preferably 0.1g/L.
4. the method for utilizing according to claim 1 the synthetic isoquercitrin of tubular microreactors enzymatic of continuous flow, is characterized in that: described enzyme liquid concentration is preferably as 0.1g/mL.
5. the method for utilizing according to claim 1 the synthetic isoquercitrin of tubular microreactors enzymatic of continuous flow, is characterized in that: the described flow velocity with micro-injection pump is controlled is preferably 2 μ L/min.
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| Application Number | Priority Date | Filing Date | Title |
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| CN201310611377.6A CN103627756A (en) | 2013-11-26 | 2013-11-26 | Method for enzymatic synthesis of isoquercitrin by using continuous-flow tubular microreactor |
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| Application Number | Priority Date | Filing Date | Title |
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| CN201310611377.6A CN103627756A (en) | 2013-11-26 | 2013-11-26 | Method for enzymatic synthesis of isoquercitrin by using continuous-flow tubular microreactor |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105969826A (en) * | 2016-06-17 | 2016-09-28 | 江苏科技大学 | Method for synthesizing isoquercitrin with nano-particle immobilized enzyme special for microreactor |
| CN106119319A (en) * | 2016-08-25 | 2016-11-16 | 江苏科技大学 | Recombinant alpha L rhamnoside enzyme extract is catalyzed the method for directionally hydrolyzing flavonoid glycoside in micro passage reaction |
| CN107056670A (en) * | 2017-06-13 | 2017-08-18 | 西安万德能源化学股份有限公司 | A kind of preparation method of two tertiary base peroxide |
| CN107988283A (en) * | 2018-01-30 | 2018-05-04 | 南京工业大学 | Method for preparing trehalose by adopting microchannel reactor |
| CN108467419A (en) * | 2018-03-23 | 2018-08-31 | 四川天添生物科技应用有限公司 | A method of synthesizing isoquercitrin with rutin |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102876746A (en) * | 2012-10-11 | 2013-01-16 | 江苏科技大学 | Method of ionic liquid cosolvent effect reinforced enzymatic synthesis of isoquercitrin |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN102876746A (en) * | 2012-10-11 | 2013-01-16 | 江苏科技大学 | Method of ionic liquid cosolvent effect reinforced enzymatic synthesis of isoquercitrin |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105969826A (en) * | 2016-06-17 | 2016-09-28 | 江苏科技大学 | Method for synthesizing isoquercitrin with nano-particle immobilized enzyme special for microreactor |
| CN105969826B (en) * | 2016-06-17 | 2019-09-27 | 江苏科技大学 | A kind of method of microreactor special-purpose nanometer particle immobilised enzymes synthesis isoquercitrin |
| CN106119319A (en) * | 2016-08-25 | 2016-11-16 | 江苏科技大学 | Recombinant alpha L rhamnoside enzyme extract is catalyzed the method for directionally hydrolyzing flavonoid glycoside in micro passage reaction |
| CN106119319B (en) * | 2016-08-25 | 2019-09-27 | 江苏科技大学 | Recombinate method of the alpha-L-Rhamnosidase crude extract for being catalyzed directionally hydrolyzing flavonoid glycoside in micro passage reaction |
| CN107056670A (en) * | 2017-06-13 | 2017-08-18 | 西安万德能源化学股份有限公司 | A kind of preparation method of two tertiary base peroxide |
| CN107988283A (en) * | 2018-01-30 | 2018-05-04 | 南京工业大学 | Method for preparing trehalose by adopting microchannel reactor |
| CN108467419A (en) * | 2018-03-23 | 2018-08-31 | 四川天添生物科技应用有限公司 | A method of synthesizing isoquercitrin with rutin |
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