CN103184254B - Method of using lipase to catalyze and synthesize mannose-6-palmitate on line - Google Patents
Method of using lipase to catalyze and synthesize mannose-6-palmitate on line Download PDFInfo
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- CN103184254B CN103184254B CN201110459188.2A CN201110459188A CN103184254B CN 103184254 B CN103184254 B CN 103184254B CN 201110459188 A CN201110459188 A CN 201110459188A CN 103184254 B CN103184254 B CN 103184254B
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Abstract
The invention discloses a method of using lipase to catalyze and synthesize mannose-6-palmitate on line. The method comprises the following steps: taking mannose and vinyl palmitate as raw materials according to molar ratio of 1:3-8, taking 0.5-1.0 g of lipase Lipozyme TLIM as a catalyst, taking tert-amyl alcohol and DMSO (dimethyl sulfoxide) mixed solvent as a reaction solvent, uniformly filling the lipase Lipozyme TLIM into 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 reaction channel is 0.5-1.0 m long, continuously introducing the raw materials and the reaction solvent into the reaction channel to perform acylation reaction, controlling the temperature of acylation reaction to be 40-55 DEG C, and keeping the acylation reaction for 15-35 min, on line collecting reaction liquid, and conventionally post-processing the reaction liquid to obtain mannose-6-palmitate. The method 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 seminose-6-cetylate of a kind of lipase-catalyzed online controlled selectivity.
(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 future development of current Surfactant Industry forward Green Chemistry, requires product toxicological harmless, renewableization of reaction raw materials, reaction process greenization gradually.Sugar ester, as a kind of good natural surface active agent, meet product toxicological harmless and the large requirement of renewableization of reaction raw materials two of Green Chemistry, but its reaction process still needs further greenization.
The sugar ester of commercially producing both at home and abroad at present is all synthesized by chemical method, there are many deficiencies in chemical method, mainly comprise: reaction process conditional is fierce, the side reaction such as sugared carbonization easily occurs and lactonize, and due to the poor selectivity of chemical synthesis to ester bond position, ester bond quantity is restive, the isomer that generation product is multiple ester and the mixture of byproduct, product is difficult to separation and purification, and product color is darker.Production by Enzymes has reaction conditions gentleness and good region and regioselectivity, and obvious stereospecificity, and product purity is high, lighter color, the 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 the shortcomings that chemical method is produced, and is more and more subject to people's attention.
At present both at home and abroad research is more and realize being still of suitability for industrialized production to take sucrose ester be two main sugar esters, and relatively less to the research of the monose esters such as lauroyl mannoses, glucose ester, fructose ester.Adopt seminose to produce sugar ester and compared many advantages with sucrose, as seminose contains that less hydroxyl, Production by Enzymes lauroyl mannoses reaction process are simpler, less side products, monoesters transformation efficiency is higher, product separation purifying is simpler etc., in addition, the research of lauroyl mannoses is solved to the single problem of the domestic sugar ester product of China by being conducive to, be conducive to realize the seriation of sugar ester HLB value.Therefore the synthetic method of developing efficient lauroyl mannoses has very important practical significance.
Micro-fluidic (Microfluidics) is in micron order structure, to control to receive to rise to technology and the science that skin rises volume fluid, is the new cross discipline emerging rapidly nearly ten years.Current, the development of micro-fluidic has surmounted the original object that is mainly 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.
From Harrison seminar in 1997, delivered after the document of first piece of writing synthetic compound in micro-fluidic chip microreactor, micro-fluidic chip reactor has been successfully used to multiple organic synthesis, and has shown application prospect widely.Along with the development of micro-mixing, micro-reaction technology in micro-fluidic chip, in chip, carry out building-up reactions and become one of the study hotspot in micro-fluidic chip field.
With conventional chemical reactor, compare, micro passage reaction not only has the diffusion length making between reactant to be shortened greatly, and mass transfer velocity is fast; The easy control of reaction conditions such as reactant ratio, temperature, reaction times and flow velocity, side reaction is less; Need reactant consumption very micro-, not only can reduce the consumption of costliness, poisonous, adverse reaction thing, and the environmental pollutant that produce in reaction process are also few, are the technology of a kind of environmental friendliness, study on the synthesis novel substance.
At present, Chinese scholars is studied the enzyme catalysis of lauroyl mannoses in organic medium is synthetic, but the method often needs the reaction times (24h) of growing, and transformation efficiency and the selectivity of reaction are not high, therefore we have studied the method for the synthetic seminose cetylate of lipase-catalyzed selectivity in micro passage reaction, are intended to find a kind of online controlled method for selective synthesis of seminose palmitinic acid monoesters of high-efficiency environment friendly.
(3) summary of the invention
The technical problem to be solved in the present invention is to provide the novel process of the synthetic seminose-6-cetylate of lipase-catalyzed selectivity in a kind of microfluidic channel reactor, has advantages of 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:
A kind of method of lipase-catalyzed online synthetic seminose-6-cetylate, described method adopts microfluidic channel reactor, described microfluidic channel reactor comprises syringe pump, syringe, reaction channel and product collector, described syringe is installed in syringe pump, by an interface, be connected with reaction channel entrance, described product collector is connected with 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: seminose and palmitinic acid vinyl acetate that the mol ratio of take is 1: 3～8 are raw material, 0.5～1.0g Lipozyme TLIM of take is catalyzer, the mixed solvent of tertiary amyl alcohol and methyl-sulphoxide (DMSO) of take is reaction solvent, raw material and reaction solvent are placed in to syringe, by Lipozyme TLIM uniform filling in the reaction channel of microfluidic channel reactor, under the promotion of syringe pump, make raw material and reaction solvent carry out acylation reaction in passing into reaction channel continuously, controlling acylation reaction temperature is 40～55 ℃, the acylation reaction time is 15～35min, by product collector, collect online reaction solution, reaction solution obtains seminose-6-cetylate through conventional aftertreatment.
In the microfluidic channel reactor that the present invention adopts, described syringe number can be one or more, depending on concrete reaction requirement.Such as, when using two syringes, can adopt T-shaped or Y type interface that different reactants is introduced from two entrances, conflux and enter public reaction channel, middle reactant molecule contact by microchannel increases with probability of collision, makes two strands of reaction solution streams in public reaction channel, mix and react.
Described microfluidic channel reactor also comprises thermostat container, and described reaction channel is placed in thermostat container, with this, can effectively control temperature of reaction.Described thermostat container can require to select voluntarily according to temperature of reaction, such as constant temperature water bath case etc.
The present invention does not limit for the material of reaction channel, and recommendation is green, the material of environmental protection, for example 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 first use the mixed solvent (tertiary amyl alcohol: DMSO=4: 1) dissolve seminose, its consumption needs only and guarantees that seminose can fully dissolve, and is loaded in syringe standby of tertiary amyl alcohol and DMSO; Only with nontoxic tertiary amyl alcohol, dissolve palmitinic acid vinyl acetate, be loaded in another syringe standby; Then for example, under promoting, syringe pump (PHD2000 syringe pump) make raw material and reaction solvent react in passing into reaction channel.Therefore, in the present invention, in reaction solvent, tertiary amyl alcohol and DMSO volume ratio are greater than 4: 1, than conventional shaking table reaction, can the usage quantity of poisonous DMSO are down to minimum.
In the present invention, the commodity that described Lipozyme TLIM is used letter (novozymes) company of Novi to produce, its be a kind of by microorganism prepare, 1,3 position-specific, the preparation of food-grade lipase (EC3.1.1.3) on particle silica gel.It obtains, with a kind of gene modification aspergillus oryzae (Aspergillus oryzae) microorganism, through submerged fermentation, produces from Thermomyces lanuginosus.
Further, the mol ratio of described seminose and palmitinic acid vinyl acetate is preferably 1: 5～and 6, most preferably be 1: 5.
Further, described acylation reaction temperature is preferably 50～55 ℃, most preferably is 52 ℃.
Further, the described acylation reaction time is preferably 30～35min, most preferably is 30min.
Reaction product of the present invention can be collected online, and gained reaction solution can obtain seminose-6-cetylate by conventional post-treating method.Described conventional post-treating method can be: the underpressure distillation of gained reaction solution is except desolventizing, with 200-300 order silica gel wet method dress post, elution reagent is chloroform: methyl alcohol=10: 1, wet method upper prop after sample dissolves with a small amount of elution reagent, collect elutriant, TLC follows the tracks of wash-out process simultaneously, and the elutriant that contains single product obtaining is merged to evaporate to dryness, can obtain milky monoesters crystal, be seminose-6-cetylate.
In the present invention, although there are 5 hydroxyls that performance is close in seminose, but the synthetic seminose-6-cetylate 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 do not have, the content of the monoesters obtaining by column chromatography for separation can reach 99%-100%.The structure warp of product
1h NMR confirmation.This shows that the enzymatic selectivity of seminose-6-cetylate in micro-fluidic micro passage reaction is synthetic and has good reaction conversion ratio and selectivity, can realize high monoesters rate.
Compared with prior art, beneficial effect of the present invention is: the synthetic seminose-6-cetylate of selectivity in 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; The usage quantity that has simultaneously reduced DMSO, has environment-friendly advantage.
(4) accompanying drawing explanation
Fig. 1 is the structural representation of the microfluidic channel reactor that adopts of embodiment.
(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 to this:
The structure of the microfluidic channel reactor that the embodiment of the present 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 syringe pump, by a Y type interface, be connected with reaction channel 3 entrances, described reaction channel 3 is placed in 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: seminose-6-cetylate synthetic
Device is with reference to figure 1: seminose (0.4mmol) is dissolved in to 10mL tertiary amyl alcohol: DMSO=4: in the mixed solvent of 1 (v/v), palmitinic acid vinyl acetate (2.0mmol) is dissolved in 10mL tertiary amyl alcohol, is then loaded on respectively in 10mL syringe standby.Lipozyme TLIM (0.87g) uniform filling is in the reaction channel of microfluidic channel reactor, and under PHD2000 syringe pump promotes, two-way reaction solution is respectively with 10.4 μ Lmin
-1flow velocity by " Y " joint, enter in reaction channel and react, by constant temperature water bath case, control temperature of reactor at 52 ℃, reaction solution is continuous flow reaction 30min in reaction channel, reaction result is followed the tracks of and is detected by thin-layer chromatography TLC.
By product collector, collect online reaction solution, underpressure distillation is except desolventizing, with 200-300 order silica gel wet method dress post, elution reagent is chloroform: methyl alcohol=10: 1, and the high 35cm of post, column diameter 4.5cm, wet method upper prop after sample dissolves with a small amount of elution reagent, elutriant is collected flow velocity 2mLmin
-1tLC follows the tracks of wash-out process simultaneously, the elutriant that contains single product obtaining is merged to evaporate to dryness, obtain white monoesters crystal, obtain seminose-6-cetylate, HPLC detects the transformation efficiency 99% of seminose, and the selectivity of seminose-6-cetylate (the lauroyl mannoses total content of the content/generation of seminose-6-cetylate) is 100%.
Nuclear-magnetism characterization result is as follows:
1h-NMR (DMSO-d6, δ, ppm): seminose-6-cetylate: 6.39 (d, 1H, J=4.5Hz, the 1-OH of α-D-MANNOSE), 4.91-4.86 (m, 2H, the H-1 of α-D-MANNOSE and the 4-OH of α-D-MANNOSE), 4.64 (d, 1H, J=4.0Hz, the 3-OH of α-D-MANNOSE), 4.56 (d, 1H, J=6.0Hz, the 2-OH of α-D-MANNOSE), 4.29 (d, 1H, J=1.5Hz, the H-6 of α-D-MANNOSE), 3.99 (m, 1H, the H-6 ' of α-D-MANNOSE), 3.72 (m, 1H, the H-5 of α-D-MANNOSE), 3.53 (m, 2H, the H-3 of α-D-MANNOSE, H-2), 3.29 (m, 1H, the H-4 of α-D-MANNOSE), 2.26 (m, 1H, a-CH
2), 2.18 (m, 1H, a-CH
2), 1.50 (m, 2H, β-CH
2), 1.24 (m, 24H, n-CH
2), 0.85 (t, 3H, J=7.0Hz, CH
3).
Embodiment 2-6
The temperature that changes microfluidic channel reactor, other are with embodiment 1, and reaction result is as shown in table 1:
Table 1: the impact of temperature on reaction
The result of table 1 shows, when flow velocity is 10.4 μ Lmin
-1reaction times is while being 30min, reaction is with the rising of temperature, transformation efficiency also obviously raises, and when temperature of reaction reaches 52 ℃, the transformation efficiency of reaction and selectivity are all best, if now continued, heat up, will cause the reduction of enzymic activity, thereby cause the selectivity of reaction to decrease, thus in the present invention in micro-fluidic micro passage reaction the optimal reaction temperature of seminose cetylate be 52 ℃.
Embodiment 6-10
Changing the substrate mol ratio of palmitinic acid vinyl acetate and seminose in micro-fluidic micro passage reaction is 3: 1 (embodiment 6), 4: 1 (embodiment 7), 6: 1 (embodiment 8), 7: 1 (embodiment 9), 8: 1 (embodiment 10), other are with embodiment 1, and result is as shown in table 2.
Table 2: seminose is compared the impact of reacting with palmitinic acid vinyl acetate substrate
The result of table 2 shows, along with the increase of reactant palmitinic acid vinyl acetate, the transformation efficiency of reaction is also along with increase, when substrate ratio is 5: 1, seminose is converted into seminose-6-palmitinic acid monoesters substantially completely, and the selectivity of reaction is also very high, almost there is no the generation of other lauroyl mannoses.If now continue to increase the consumption of reactant palmitinic acid vinyl acetate, can cause on the contrary transformation efficiency and the elective reduction of reaction.Thereby the best substrate ratio of reaction of the present invention is 5: 1, under this reaction conditions, seminose substantially quantitatively transforms the cetylate for seminose-6-completely.
Embodiment 11-14
Changing the reaction times in micro-fluidic micro passage reaction is 15min (embodiment 11), 20min (embodiment 12), 25min (embodiment 13), 35min (embodiment 14), and other are with embodiment 1, and result is as shown in table 3.
Table 3: the reaction times is on reaction conversion ratio and optionally impact
The result of table 3 shows, increase along with the reaction times, the transformation efficiency of reaction increases gradually, when 30min is carried out in reaction, the transformation efficiency of reaction and selectivity are optimum, if now continue to extend the reaction times, will cause reaction conversion ratio and optionally reduce, thereby the synthetic Best Times of seminose-6-cetylate is 30min in microfluidic channel reactor.
Claims (6)
1. the method for lipase-catalyzed online synthetic seminose-6-cetylate, it is characterized in that described method adopts microfluidic channel reactor, described microfluidic channel reactor comprises syringe pump, syringe, reaction channel and product collector, described syringe is installed in syringe pump, by an interface, be connected with reaction channel entrance, described product collector is connected with 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: seminose and palmitinic acid vinyl acetate that the mol ratio of take is 1: 3～8 are raw material, 0.5～1.0g Lipozyme TLIM of take is catalyzer, the mixed solvent of tertiary amyl alcohol and methyl-sulphoxide of take is reaction solvent, raw material and reaction solvent are placed in to syringe, by Lipozyme TLIM uniform filling in reaction channel, under the promotion of syringe pump, make raw material and reaction solvent carry out acylation reaction in passing into reaction channel continuously, controlling acylation reaction temperature is 40～55 ℃, the acylation reaction time is 15～35min, by product collector, collect online reaction solution, reaction solution obtains seminose-6-cetylate through conventional aftertreatment.
2. the method for lipase-catalyzed online synthetic seminose-6-cetylate as claimed in claim 1, it is characterized in that: the tertiary amyl alcohol that it is first 4: 1 by volume ratio that described method comprises the following steps: and the mixed solvent of DMSO dissolve seminose, are loaded in syringe standby; With tertiary amyl alcohol, dissolve palmitinic acid vinyl acetate, be loaded in another syringe standby; Then under promoting, syringe pump make raw material and reaction solvent carry out acylation reaction in passing into reaction channel.
3. the method for lipase-catalyzed online synthetic seminose-6-cetylate as claimed in claim 1, is characterized in that: described microfluidic channel reactor comprises thermostat container, and described reaction channel is placed in thermostat container.
4. the method for lipase-catalyzed online synthetic seminose-6-cetylate as claimed in claim 2, is characterized in that: described microfluidic channel reactor comprises thermostat container, and described reaction channel is placed in thermostat container.
5. the method for the lipase-catalyzed online synthetic seminose-6-cetylate as described in one of claim 1～4; it is characterized in that: the mol ratio of described seminose and palmitinic acid vinyl acetate is 1: 5～6; described acylation reaction temperature is 50～55 ℃, and the described acylation reaction time is 30～35min.
6. the method for the lipase-catalyzed online synthetic seminose-6-cetylate as described in one of claim 1～4; it is characterized in that: the mol ratio of described seminose and palmitinic acid vinyl acetate is 1: 5; described acylation reaction temperature is 52 ℃, and the described acylation reaction time is 30min.
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| CN107604024A (en) * | 2017-08-21 | 2018-01-19 | 浙江工业大学 | A kind of method of lipase-catalyzed online synthesis N (5 lauroyl mannoses valeryl) mexiletine |
| CN111455004B (en) * | 2020-02-29 | 2023-05-05 | 浙江农林大学 | Method for synthesizing coumarin-3-carboxylic acid-6' -O-D-mannose ester on line by lipase catalysis |
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| CN101507909A (en) * | 2009-02-25 | 2009-08-19 | 中国科学院过程工程研究所 | Molecular engram microspheres preparation method using micro-fluidic reactor |
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| CN101507909A (en) * | 2009-02-25 | 2009-08-19 | 中国科学院过程工程研究所 | Molecular engram microspheres preparation method using micro-fluidic reactor |
Non-Patent Citations (4)
| Title |
|---|
| Lipase‐catalyzed regioselective acylation of sucrose in two‐solvent mixtures;Manuel Ferrer et al;《Biotechnology and Bioengineering》;19991005;第65卷(第1期);第10-16页 * |
| Manuel Ferrer et al.Lipase‐catalyzed regioselective acylation of sucrose in two‐solvent mixtures.《Biotechnology and Bioengineering》.1999,第65卷(第1期),第10-16页. * |
| 吴克庆等.酶促反应合成蔗糖棕榈酸酯的研究.《中国油脂》.2004,第29卷(第3期),第37-39页. * |
| 酶促反应合成蔗糖棕榈酸酯的研究;吴克庆等;《中国油脂》;20041231;第29卷(第3期);第37-39页 * |
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