CN103184251A - Method for on-line synthesizing glucose-6-acetate catalyzed by lipase - Google Patents
Method for on-line synthesizing glucose-6-acetate catalyzed by lipase Download PDFInfo
- Publication number
- CN103184251A CN103184251A CN2011104575216A CN201110457521A CN103184251A CN 103184251 A CN103184251 A CN 103184251A CN 2011104575216 A CN2011104575216 A CN 2011104575216A CN 201110457521 A CN201110457521 A CN 201110457521A CN 103184251 A CN103184251 A CN 103184251A
- Authority
- CN
- China
- Prior art keywords
- reaction
- glucose
- lipase
- acetic ester
- channel
- 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
Images
Landscapes
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Apparatus Associated With Microorganisms And Enzymes (AREA)
Abstract
The invention discloses a method for on-line synthesizing glucose-6-acetate catalyzed by lipase. According to the method, glucose and vinyl acetate with a molar ratio being 1 : 16-22 are used as raw materials; 0.5-1.0 g of the lipase (Lipozyme TLIM) is used as a catalyst and a mixed solvent formed by tert-amyl alcohol and DMSO is used as a reaction solvent. The lipase (Lipozyme TLIM) is uniformly filled in a reaction channel of a microfluidic channel reactor, wherein the inner diameter of the reaction channel of the microfluidic channel reactor is 0.8-2.4 mm, and the length of the reaction channel is 0.5-1.0 m; the raw materials and the reaction solvent are continuously introduced into the reaction channel for an acylation reaction, wherein the temperature of the acylation reaction is controlled at 40-55 DEG C and the time of the acylation reaction is 15-35 min; a reaction liquid is collected on-line; and the glucose-6-acetate is obtained after the reaction liquid is subjected to conventional post-treatment. The method provided by the invention has the advantages of short reaction time, high selectivity and high yield.
Description
(1) technical field
The present invention relates to the method for the synthetic glucose of a kind of lipase-catalyzed online controlled selectivity-6-acetic ester.
(2) background technology
Sugar ester is a kind of good nonionogenic tenside, and the natural reproducible resource sugar that adopts nature extensively to exist is raw material, has vast potential for future development.The direction of current tensio-active agent industry forward Green Chemistry develops, and requires product toxicological harmlessization, renewableization of reaction raw materials, reaction process greenization gradually.Sugar ester meet product toxicological harmlessization and the two big requirements of renewableization of reaction raw materials of Green Chemistry, but its reaction process still needs further greenization as a kind of good natural surface active agent.
The sugar ester of commercially producing both at home and abroad at present is all synthetic by chemical method, there are many deficiencies in chemical method, mainly comprise: condition fierceness in the reaction process, side reaction such as the carbonization of sugar takes place easily and lactonize, and owing to the poor selectivity of chemosynthesis reaction to the ester bond position, ester bond quantity is restive, and generating product is the isomer of multiple ester and the mixture of byproduct, shortcomings such as product is difficult to separation and purification, and product color is darker.Production by Enzymes has gentle and good zone and the regioselectivity of reaction conditions, and tangible stereospecificity, product purity height, lighter color, advantages such as the easy separation and purification of product.Production by Enzymes not only meets the requirement of green reaction process, and has solved many shortcomings that chemical method is produced, and more and more is subject to people's attention.
Research at present both at home and abroad is more and realize two sugar esters based on sucrose ester of being still of suitability for industrialized production, and less relatively to the research of monose esters such as glucose ester, fructose ester.Adopt the glucose production sugar ester to compare many advantages with sucrose, contain less hydroxyl as glucose, Production by Enzymes glucose ester reaction process is simpler, less side products, the monoesters transformation efficiency is higher, the product separation purifying is simpler etc., in addition, will be conducive to solve the single problem of the domestic sugar ester product of China to the research of glucose ester, be conducive to realize the seriation of sugar ester HLB value.
Therefore developing efficiently, the synthetic method of glucose ester has very important and practical meanings.
Micro-fluidic (Microfluidics) is to control to receive in the micron order structure to rise to technology and the science that skin rises the volume fluid, is the new cross discipline that emerges rapidly over past ten years.Current, the development of micro-fluidic has surmounted the original purpose that is mainly the analytical chemistry service greatly, and is becoming the important technological platform of whole chemistry subject, life science, instrumental science and even information science new round innovation research.
After Harrison seminar in 1997 had delivered the document of first piece of writing synthetic compound in the micro-fluidic chip microreactor, the micro-fluidic chip reactor had been successfully used to multiple organic synthesis, and has showed application prospect widely.Along with the development of little mixing, little reaction technology in the micro-fluidic chip, in chip, carry out building-up reactions and become one of the research focus in micro-fluidic chip field.
Compare with the conventional chemical reactor, micro passage reaction not only has the diffusion length that makes between reactant to be shortened greatly, and mass transfer velocity is fast; Easy control of reaction conditions such as reactant ratio, temperature, reaction times and flow velocity, side reaction is less; Need the reactant consumption very little, not only can reduce the consumption of costliness, poisonous, adverse reaction thing, the environmental pollutant that produce in the reaction process are also few, are the technology of a kind of environmental friendliness, study on the synthesis novel substance.
At present, there is more Chinese scholars to study the enzyme catalysis of glucose ester in the organic medium is synthetic, but this method often needs the long reaction times (24h), and transformation efficiency and the selectivity of reaction are not high, therefore we have studied the method for the synthetic glucose of lipase-catalyzed selectivity-6-acetic ester in the micro passage reaction, are intended to seek a kind of online controlled method for selective synthesis of glucose-6-acetic acid monoesters of high-efficiency environment friendly.
(3) summary of the invention
The technical problem to be solved in the present invention provides the novel process of the synthetic glucose of lipase-catalyzed selectivity-6-acetic ester in a kind of microfluidic channel reactor, has the advantage that the reaction times is short, selectivity is high and productive rate is high.
For solving the problems of the technologies described above, the present invention adopts following technical scheme:
The method of a kind of lipase-catalyzed online synthesis of glucose-6-acetic ester, described method adopts the microfluidic channel reactor, described microfluidic channel reactor comprises syringe pump, syringe, reaction channel and product collector, described syringe is installed in the syringe pump, be connected with the reaction channel entrance by an interface, described product collector is connected with the reaction channel outlet by an interface, and described reaction channel internal diameter is 0.8～2.4mm, and reaction channel length is 0.5～1.0m; Described method comprises: be that 1: 16～22 glucose and vinyl-acetic ester are raw material with mol ratio; be catalyzer with 0.5～1.0g lipase Lipozyme TLIM; mixed solvent with tertiary amyl alcohol and methyl-sulphoxide (DMSO) is reaction solvent; raw material and reaction solvent are placed syringe; evenly be filled in lipase Lipozyme TLIM in the reaction channel; under syringe pump promotes, raw material and reaction solvent are fed continuously and carry out acylation reaction in the reaction channel; control acylation reaction temperature is 40～55 ℃; the acylation reaction time is 15～35min; by the online collection reaction solution of product collector, reaction solution obtains glucose-6-acetic ester through conventional aftertreatment.
In the microfluidic channel reactor that the present invention adopts, described syringe number can be one or more, decides on concrete reaction requirement.Such as, when using two syringes, can adopt T type or Y type interface that different reactants is introduced from two entrances, conflux and enter public reaction channel, middle reactant molecule contact by the microchannel increases with probability of collision, two strands of reaction solutions streams are mixed in public reaction channel and reacts.
Described microfluidic channel reactor also comprises thermostat container, and described reaction channel places thermostat container, can effectively control temperature of reaction with this.Described thermostat container can require to select voluntarily according to temperature of reaction, such as the constant temperature water bath case etc.
The present invention does not limit for the material of reaction channel, recommends to use material green, environmental protection, as silicone tube; Shape for reaction channel is preferably curved shape, can guarantee at the uniform velocity stable the passing through of reaction solution.
The present invention in implementation process, can be earlier (tertiary amyl alcohol: DMSO=4: 1) dissolving glucose, its consumption is as long as guarantee that glucose can fully dissolve, and is loaded in the syringe standby with the mixed solvent of tertiary amyl alcohol and DMSO; Only with nontoxic tertiary amyl alcohol dissolving vinyl-acetic ester, be loaded in another syringe standby; Raw material and reaction solvent are fed in the reaction channel to react.Therefore, among the present invention, tertiary amyl alcohol and DMSO volume ratio than the shaking table reaction of routine, can be down to the usage quantity of poisonous DMSO minimum greater than 4: 1 in the reaction solvent.
Among the present invention, the commodity that described lipase Lipozyme TLIM uses letter (novozymes) company of Novi to produce, it is a kind of by microorganism preparation, 1,3 position-specific, the preparation of food-grade lipase (EC3.1.1.3) on particle silica gel.It obtains, produces through submerged fermentation with a kind of gene modification aspergillus oryzae (Aspergillus oryzae) microorganism from Thermomyces lanuginosus.
Further, the mol ratio of described glucose and vinyl-acetic ester is preferably 1: 20～and 22, most preferably be 1: 20.
Further, described acylation reaction temperature is preferably 52～55 ℃, most preferably is 52 ℃.
Further, the described acylation reaction time is preferably 25～35min, most preferably is 30min.
Reaction product of the present invention can onlinely be collected, and the gained reaction solution can obtain glucose-6-acetic ester by conventional post-treating method.Described conventional post-treating method can be: gained reaction solution underpressure distillation desolventizing, with 200-300 order silica gel wet method dress post, elution reagent is chloroform: methyl alcohol=10: 1, sample dissolves back wet method upper prop with a small amount of elution reagent, collect elutriant, TLC follows the tracks of the wash-out process simultaneously, and the elutriant that contains single product that obtains is merged evaporate to dryness, can obtain the monoesters crystal of white, be glucose-6-acetic ester.
Among the present invention, though 5 hydroxyls that performance is close are arranged in glucose, but the synthetic glucose acetate of lipase-catalyzed selectivity has higher transformation efficiency and selectivity in micro-fluidic micro passage reaction, the transformation efficiency of diester is very low, almost there is not the content 100% of the monoesters that obtains by column chromatography for separation.The structure warp of product
1H NMR conclusive evidence.This shows that the enzymatic selectivity of glucose acetate in the microfluidic channel reactor is synthetic and has good reaction conversion ratio and selectivity, can realize high mono-esterification rate.
Compared with prior art, beneficial effect of the present invention is: the synthetic glucose of selectivity-6-acetic ester in the microfluidic channel reactor of the present invention, and this method has not only shortened the reaction times widely, and has high transformation efficiency and reaction preference; Reduce the usage quantity of DMSO simultaneously, had environment-friendly advantage.
(4) description of drawings
Fig. 1 is the structural representation of the microfluidic channel reactor of embodiment of the invention employing.
(5) embodiment
With specific embodiment protection scope of the present invention is described further below, but protection scope of the present invention is not limited thereto:
The structure of the microfluidic channel reactor that the embodiment of the invention is used is with reference to figure 1, comprises a syringe pump (not shown), two syringes 1 and 2, reaction channel 3, constant temperature water bath case (5, only show its floor map) and product collector 4; Two syringes 1 and 2 are installed in the syringe pump, be connected with reaction channel 3 entrances by a Y type interface, described reaction channel 3 places constant temperature water bath case 5, by constant temperature water bath case 5 control temperature of reaction, the internal diameter 2.4mm of described reaction channel 3, the long 1m of reaction channel, described reaction channel 3 outlets are connected with product collector 4 by an interface.
Embodiment 1: glucose-6-acetic ester synthetic
Device is with reference to figure 1: (0.4mmol) is dissolved in 10mL tertiary amyl alcohol: DMSO=4 with glucose: in the mixed solvent of 1 (v/v), vinyl-acetic ester (8.0mmol) is dissolved in the 10mL tertiary amyl alcohol, is loaded in the 10mL syringe standby then respectively.0.87g lipase Lipozyme TLIM evenly is filled in the reaction channel of microfluidic channel reactor, under the PHD2000 syringe pump promoted, the two-way reaction solution was respectively with 10.4 μ Lmin
-1Flow velocity enter in the reaction channel by " Y " joint and react, at 52 ℃, reaction solution is continuous flow reaction 30min in reaction channel by constant temperature water bath case control temperature of reactor, reaction result is followed the tracks of by thin-layer chromatography TLC and is detected.
By the online collection reaction solution of product collector, the underpressure distillation desolventizing is with 200-300 order silica gel wet method dress post, elution reagent is chloroform: methyl alcohol=10: 1, the high 35cm of post, column diameter 4.5cm, sample dissolves back wet method upper prop with a small amount of elution reagent, and elutriant is collected flow velocity 2mLmin
-1TLC follows the tracks of the wash-out process simultaneously, the elutriant that contains single product that obtains is merged evaporate to dryness, obtain the monoesters crystal of white, obtain glucose-6-acetic ester, HPLC measures inversion rate of glucose 99%, and glucose-6-acetic ester selectivity (the glucose ester total content of glucose-6-acetate content/generation) is 100%.
The nuclear-magnetism characterization result is as follows:
1H-NMR (DMSO-d6, δ, ppm): glucose-6-acetic ester:
1H-NMR (DMSO-d6, δ, ppm): 6.71 (d, 0.5H, J=6.5Hz, the 1-OH of β-D-glucose), 6.36 (d, 0.5H, J=4.5Hz, the 1-OH of alpha-D-glucose), (5.15-4.57 br m, other OH of D-glucose), 4.32 (m, 1.5H, the H-6 of D-glucose (1H) and β H-1 (0.5H)), 4.0 (m, 1H, the H-6 ' of D-glucose), 3.77 (m, 0.5H, the α H-5 of D-glucose), 3.39-3.30,3.13,3.03 (br m, other α of D-glucose or β H), (2.90 0.5H, m, the β H-2 of D-glucose), 2.00 (3H, s, CH
3).
Embodiment 2-5
Change the temperature of microfluidic channel reactor, other are with embodiment 1, and reaction result is as shown in table 1:
Table 1: temperature is to the influence of reaction
The result of table 1 shows, when flow velocity is 10.4 μ Lmin
-1Reaction times is when being 30min, reaction is with the rising of temperature, transformation efficiency also obviously raises, and when temperature of reaction reached 52 ℃, the transformation efficiency of reaction and selectivity were all best, heat up if continue this moment, will cause the reduction of enzymic activity, thereby cause transformation efficiency and the selectivity of reaction to decrease, thus among the present invention in the micro-fluidic micro passage reaction optimal reaction temperature of glucose acetate be 52 ℃.
Embodiment 6-10
Change that the substrate mol ratio of vinyl-acetic ester and glucose is 16: 1 (embodiment 6), 17: 1 (embodiment 7), 18: 1 (embodiment 8), 19: 1 (embodiment 9), 21: 1 (embodiment 10), 22: 1 (embodiment 11) in the micro-fluidic micro passage reaction, other are with embodiment 1, and the result is as shown in table 2.
Table 2: the influence of glucose and vinyl-acetic ester substrate comparison reaction
| Embodiment | Vinyl-acetic ester: glucose | Transformation efficiency [%] | Selectivity [%] |
| 6 | 16∶1 | 65 | 100 |
| 7 | 17∶1 | 75 | 100 |
| 8 | 18∶1 | 84 | 100 |
| 9 | 19∶1 | 90 | 100 |
| 1 | 20∶1 | 99 | 100 |
[0042]
| 10 | 21∶1 | 98 | 99 |
| 11 | 22∶1 | 98 | 98 |
The result of table 2 shows that along with the increase of reactant vinyl-acetic ester, the transformation efficiency of reaction is also along with increase, and when the substrate ratio was 20: 1, the transformation efficiency of reaction and selectivity optimum, glucose substantially quantitatively transformed fully for glucose-6-acetic ester.If continue to increase the consumption of reactant vinyl-acetic ester this moment, transformation efficiency and the selectivity that will cause reacting reduce, thereby the best substrate ratio of this reaction is 20: 1, under this reaction conditions, glucose substantially quantitatively transforms fully for glucose-6-acetic ester.
Embodiment 12-15
Change that the reaction times is 15min (embodiment 12), 20min (embodiment 13), 25min (embodiment 14), 35min (embodiment 15) in the micro-fluidic micro passage reaction, other are with embodiment 1, and the result is as shown in table 3.
Table 3: the reaction times is to reaction conversion ratio and optionally influence
| Embodiment | Reaction times [min] | Transformation efficiency [%] | Selectivity [%] |
| 12 | 15 | 65 | 100 |
| 13 | 20 | 86 | 100 |
| 14 | 25 | 93 | 100 |
| 1 | 30 | 99 | 100 |
| 15 | 35 | 98 | 99 |
The result of table 3 shows that reaction is carried out 15min and can be obtained glucose-6-acetic acid monoesters of 65%, and the selectivity of this moment is 100%, and glucose is to be converted into glucose-6-acetic acid monoesters fully substantially.Along with the increase in reaction times, the transformation efficiency of reaction increases gradually, when 30min is carried out in reaction, and the transformation efficiency of reaction and selectivity optimum, glucose-6-acetic acid monoesters transforms substantially fully, and reaction preference also can reach 100%.If continue this moment to prolong the reaction times, can cause reaction conversion ratio and optionally reduction on the contrary, thereby the synthetic Best Times of glucose in the microfluidic channel reactor-6-acetic ester is 30min.
Claims (6)
1. the method for lipase-catalyzed online synthesis of glucose-6-acetic ester, it is characterized in that described method adopts the microfluidic channel reactor, described microfluidic channel reactor comprises syringe pump, syringe, reaction channel and product collector, described syringe is installed in the syringe pump, be connected with the reaction channel entrance by an interface, described product collector is connected with the reaction channel outlet by an interface, described reaction channel internal diameter is 0.8～2.4mm, and reaction channel length is 0.5～1.0m; Described method comprises: be that 1: 16～22 glucose and vinyl-acetic ester are raw material with mol ratio; be catalyzer with 0.5～1.0g lipase Lipozyme TLIM; mixed solvent with tertiary amyl alcohol and methyl-sulphoxide (DMSO) is reaction solvent; raw material and reaction solvent are placed syringe; evenly be filled in lipase Lipozyme TLIM in the reaction channel; under syringe pump promotes, raw material and reaction solvent are fed continuously and carry out acylation reaction in the reaction channel; control acylation reaction temperature is 40～55 ℃; the acylation reaction time is 15～35min; by the online collection reaction solution of product collector, reaction solution obtains glucose-6-acetic ester through conventional aftertreatment.
2. the method for lipase-catalyzed online synthesis of glucose as claimed in claim 1-6-acetic ester, it is characterized in that: described method comprises the following steps: to be 4: 1 tertiary amyl alcohol and the mixed solvent dissolving glucose of DMSO with volume ratio earlier, is loaded in the syringe standby; Dissolve vinyl-acetic ester with tertiary amyl alcohol, be loaded in another syringe standby; Raw material and reaction solvent are fed in the reaction channel carry out acylation reaction.
3. the method for lipase-catalyzed online synthesis of glucose as claimed in claim 1-6-acetic ester, it is characterized in that: described microfluidic channel reactor comprises thermostat container, and described reaction channel places thermostat container.
4. the method for lipase-catalyzed online synthesis of glucose as claimed in claim 2-6-acetic ester, it is characterized in that: described microfluidic channel reactor comprises thermostat container, and described reaction channel places thermostat container.
5. as the method for the described lipase-catalyzed online synthesis of glucose of one of claim 1～4-6-acetic ester; it is characterized in that: the mol ratio of described glucose and vinyl-acetic ester is 1: 20～22; described acylation reaction temperature is 52～55 ℃, and the described acylation reaction time is 25～35min.
6. as the method for the described lipase-catalyzed online synthesis of glucose of one of claim 1～4-6-acetic ester; it is characterized in that: the mol ratio of described glucose and vinyl-acetic ester is 1: 20; described acylation reaction temperature is 52 ℃, and the described acylation reaction time is 30min.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201110457521.6A CN103184251B (en) | 2011-12-31 | 2011-12-31 | Method for on-line synthesizing glucose-6-acetate catalyzed by lipase |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201110457521.6A CN103184251B (en) | 2011-12-31 | 2011-12-31 | Method for on-line synthesizing glucose-6-acetate catalyzed by lipase |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN103184251A true CN103184251A (en) | 2013-07-03 |
| CN103184251B CN103184251B (en) | 2014-11-12 |
Family
ID=48675697
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201110457521.6A Active CN103184251B (en) | 2011-12-31 | 2011-12-31 | Method for on-line synthesizing glucose-6-acetate catalyzed by lipase |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN103184251B (en) |
Cited By (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107418989A (en) * | 2017-08-21 | 2017-12-01 | 浙江工业大学 | A kind of method of lipase-catalyzed online synthesis N (5 sucrose ester valeryl) metoprolol |
| CN107475329A (en) * | 2017-08-21 | 2017-12-15 | 浙江工业大学 | A kind of method of lipase-catalyzed online synthesis N (5 sucrose ester valeryl) mexiletine |
| CN107475330A (en) * | 2017-08-21 | 2017-12-15 | 浙江工业大学 | A kind of method of lipase-catalyzed online synthesis N (5 glucose ester valeryl) metoprolol |
| CN107488690A (en) * | 2017-08-21 | 2017-12-19 | 浙江工业大学 | A kind of method of lipase-catalyzed online synthesis N (5 glucose ester valeryl) mexiletine |
| CN107488691A (en) * | 2017-08-21 | 2017-12-19 | 浙江工业大学 | A kind of method of lipase-catalyzed online synthesis N (5 lauroyl mannoses valeryl) metoprolol |
| CN107488683A (en) * | 2017-08-21 | 2017-12-19 | 浙江工业大学 | A kind of lipase-catalyzed online synthesis N（5 vinyl acetate valeryls）The method of mexiletine |
| CN107502629A (en) * | 2017-08-21 | 2017-12-22 | 浙江工业大学 | A kind of lipase-catalyzed online synthesis N（5 vinyl acetate valeryls）The method of metoprolol |
| CN107955823A (en) * | 2017-12-21 | 2018-04-24 | 浙江工业大学 | A kind of method of lipase-catalyzed online synthesis 6- ((4- methyl-benzyls) sulfenyl) -6- oxo vinyl caproates |
| CN107955822A (en) * | 2017-12-21 | 2018-04-24 | 浙江工业大学 | A kind of lipase-catalyzed online synthesis S-（4- methyl-benzyls）The method of laurate thioesters |
| CN107955824A (en) * | 2017-12-21 | 2018-04-24 | 浙江工业大学 | A kind of lipase-catalyzed online synthesis S-（4- chlorobenzyls）The method of laurate thioesters |
| CN107988279A (en) * | 2017-12-21 | 2018-05-04 | 浙江工业大学 | A kind of method of lipase-catalyzed online synthesis 6- ((4- chlorobenzyls) sulfenyl) -6- oxo vinyl caproates |
| CN107988278A (en) * | 2017-12-21 | 2018-05-04 | 浙江农林大学 | A kind of method of lipase-catalyzed online synthesis S- benzyl laurate thioesters |
| CN107988277A (en) * | 2017-12-21 | 2018-05-04 | 浙江农林大学 | A kind of method of lipase-catalyzed online synthesis S- benzyl palmitic acid thioesters |
| CN108060184A (en) * | 2017-12-21 | 2018-05-22 | 浙江工业大学 | A kind of method of lipase-catalyzed online synthesis S- thioacetic acid benzyl esters |
| CN108060185A (en) * | 2017-12-21 | 2018-05-22 | 浙江工业大学 | A kind of method of lipase-catalyzed online synthesis S- (4- methylbenzyls) thiacetate |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100367033C (en) * | 2005-04-21 | 2008-02-06 | 南京大学 | Microflow control chip integrated unit in integrated constant temperature system in high efficiency |
| CN102161683A (en) * | 2011-02-24 | 2011-08-24 | 浙江工业大学 | Method for synthesizing sucrose-6-palmitate by using lipase through catalytic selectivity |
-
2011
- 2011-12-31 CN CN201110457521.6A patent/CN103184251B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100367033C (en) * | 2005-04-21 | 2008-02-06 | 南京大学 | Microflow control chip integrated unit in integrated constant temperature system in high efficiency |
| CN102161683A (en) * | 2011-02-24 | 2011-08-24 | 浙江工业大学 | Method for synthesizing sucrose-6-palmitate by using lipase through catalytic selectivity |
Non-Patent Citations (5)
| Title |
|---|
| PEDRO FERNANDES: "Miniaturization in Biocatalysis", 《INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES》 * |
| POLONA ZNIDARSIC PLAZL,ET AL.: "Modelling and experimental studies on lipase-catalyzed isoamyl acetate synthesis in a microreactor", 《PROCESS BIOCHEMISTRY》 * |
| 任昌琼等: "重组脂肪酶全细胞催化单糖酯的合成", 《现代食品科技》 * |
| 李军生等: "脂肪酶催化合成蔗糖-6-月桂酸单酯的研究", 《广西工学院学报》 * |
| 钟平等: "微反应器技术在有机合成中的应用", 《化学试剂》 * |
Cited By (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107418989A (en) * | 2017-08-21 | 2017-12-01 | 浙江工业大学 | A kind of method of lipase-catalyzed online synthesis N (5 sucrose ester valeryl) metoprolol |
| CN107475329A (en) * | 2017-08-21 | 2017-12-15 | 浙江工业大学 | A kind of method of lipase-catalyzed online synthesis N (5 sucrose ester valeryl) mexiletine |
| CN107475330A (en) * | 2017-08-21 | 2017-12-15 | 浙江工业大学 | A kind of method of lipase-catalyzed online synthesis N (5 glucose ester valeryl) metoprolol |
| CN107488690A (en) * | 2017-08-21 | 2017-12-19 | 浙江工业大学 | A kind of method of lipase-catalyzed online synthesis N (5 glucose ester valeryl) mexiletine |
| CN107488691A (en) * | 2017-08-21 | 2017-12-19 | 浙江工业大学 | A kind of method of lipase-catalyzed online synthesis N (5 lauroyl mannoses valeryl) metoprolol |
| CN107488683A (en) * | 2017-08-21 | 2017-12-19 | 浙江工业大学 | A kind of lipase-catalyzed online synthesis N（5 vinyl acetate valeryls）The method of mexiletine |
| CN107502629A (en) * | 2017-08-21 | 2017-12-22 | 浙江工业大学 | A kind of lipase-catalyzed online synthesis N（5 vinyl acetate valeryls）The method of metoprolol |
| CN107955823A (en) * | 2017-12-21 | 2018-04-24 | 浙江工业大学 | A kind of method of lipase-catalyzed online synthesis 6- ((4- methyl-benzyls) sulfenyl) -6- oxo vinyl caproates |
| CN107955822A (en) * | 2017-12-21 | 2018-04-24 | 浙江工业大学 | A kind of lipase-catalyzed online synthesis S-（4- methyl-benzyls）The method of laurate thioesters |
| CN107955824A (en) * | 2017-12-21 | 2018-04-24 | 浙江工业大学 | A kind of lipase-catalyzed online synthesis S-（4- chlorobenzyls）The method of laurate thioesters |
| CN107988279A (en) * | 2017-12-21 | 2018-05-04 | 浙江工业大学 | A kind of method of lipase-catalyzed online synthesis 6- ((4- chlorobenzyls) sulfenyl) -6- oxo vinyl caproates |
| CN107988278A (en) * | 2017-12-21 | 2018-05-04 | 浙江农林大学 | A kind of method of lipase-catalyzed online synthesis S- benzyl laurate thioesters |
| CN107988277A (en) * | 2017-12-21 | 2018-05-04 | 浙江农林大学 | A kind of method of lipase-catalyzed online synthesis S- benzyl palmitic acid thioesters |
| CN108060184A (en) * | 2017-12-21 | 2018-05-22 | 浙江工业大学 | A kind of method of lipase-catalyzed online synthesis S- thioacetic acid benzyl esters |
| CN108060185A (en) * | 2017-12-21 | 2018-05-22 | 浙江工业大学 | A kind of method of lipase-catalyzed online synthesis S- (4- methylbenzyls) thiacetate |
| CN107988278B (en) * | 2017-12-21 | 2021-06-04 | 浙江农林大学 | Method for synthesizing S-benzyl lauric acid thioester on line by lipase catalysis |
| CN107988277B (en) * | 2017-12-21 | 2021-06-08 | 浙江农林大学 | Method for synthesizing S-benzylpalmitic acid thioester on line under catalysis of lipase |
Also Published As
| Publication number | Publication date |
|---|---|
| CN103184251B (en) | 2014-11-12 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN103184249B (en) | Method for on-line synthesizing glucose-6-palmitate by lipase catalysis | |
| CN103184251B (en) | Method for on-line synthesizing glucose-6-acetate catalyzed by lipase | |
| CN103184252B (en) | Method of using lipase to catalyze and synthesize glucose-6-laurate on line | |
| CN103184253B (en) | Method of using lipase to catalyze and synthesize mannose-6-laurate on line | |
| CN103184255B (en) | Method of using lipase to catalyze and synthesize galactose-6-acetate on line | |
| CN103184257B (en) | Method for on-line synthesizing sucrose-6-acetate catalyzed by lipase | |
| CN103184256B (en) | Method for on-line synthesizing saccharose-6-laurate by lipase catalysis | |
| CN103667402B (en) | A kind of lipase-catalyzed online synthesis 6 " method of-O-lauroyl-naringin ester | |
| CN105838600B (en) | A kind of method of 5 ' O palmityl uridines of lipase-catalyzed online synthesis | |
| CN107384991B (en) | Method for synthesizing 5' -O-ethylene adipamide uridine on line by lipase catalysis | |
| CN103667396B (en) | A kind of lipase-catalyzed online synthesis 6 " method of-O-lauroyl-naringin dihydrochalcone ester | |
| CN103182277B (en) | Microfluidic channel reactor and the application in synthesis of sucrose-6-palmitate thereof | |
| CN107988277B (en) | Method for synthesizing S-benzylpalmitic acid thioester on line under catalysis of lipase | |
| CN107384782A (en) | A kind of method of lipase-catalyzed online synthesis 5 '-O- ethene adipyls -5-FUD | |
| CN103667400B (en) | A kind of lipase-catalyzed online synthesis 6 " method of-O-palmityl-naringin ester | |
| CN103667393B (en) | A kind of lipase-catalyzed online synthesis 6 " method of-O-palmityl-neohesperidin dihydrochalcone ester | |
| CN103184254B (en) | Method of using lipase to catalyze and synthesize mannose-6-palmitate on line | |
| CN103184250B (en) | Method for on-line synthesizing mannose-6-acetate by lipase catalysis | |
| CN103667394B (en) | A kind of lipase-catalyzed online synthesis 6 " method of-O-lauroyl-neohesperidin dihydrochalcone ester | |
| CN104561170A (en) | Method for synthesizing 1-(6-nitrobenzimidazolyl)ethyl acetate on line under catalysis of lipase | |
| CN105838599B (en) | A kind of method of 5 '-O- lauroyl uridines of lipase-catalyzed online synthesis | |
| CN103667399B (en) | A kind of lipase-catalyzed online synthesis 6 " method of-O-palmityl-Neohesperidin ester | |
| CN107988278B (en) | Method for synthesizing S-benzyl lauric acid thioester on line by lipase catalysis | |
| CN103667401B (en) | A kind of lipase-catalyzed online synthesis 6 " method of-O-lauroyl-Neohesperidin ester | |
| CN107384993A (en) | A kind of method of lipase-catalyzed online synthesis 5 '-O- acetyl -5-methyl-uridin |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant |