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Method of using lipase to catalyze and synthesize mannose-6-palmitate on line

A technology of palmitate and mannose, applied in biochemical equipment and methods, biochemical instruments, biochemical cleaning devices, etc., can solve the problems of low conversion rate and selectivity, long reaction time, etc., to shorten the reaction time, Effects of reduced usage, high conversion and reaction selectivity

Active Publication Date: 2013-07-03
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] At present, scholars at home and abroad have studied the enzyme-catalyzed synthesis of mannose esters in organic media, but this method often requires a long reaction time (24h), and the conversion rate and selectivity of the reaction are not high. A lipase-catalyzed selective synthesis of mannose palmitate in a channel reactor, aiming to find an efficient and environmentally friendly online controllable selective synthesis of mannose palmitate monoester

Method used

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  • Method of using lipase to catalyze and synthesize mannose-6-palmitate on line
  • Method of using lipase to catalyze and synthesize mannose-6-palmitate on line
  • Method of using lipase to catalyze and synthesize mannose-6-palmitate on line

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Example 1: Synthesis of Mannose-6-palmitate

[0027]

[0028] device reference figure 1 : Mannose (0.4mmol) was dissolved in 10mL of tert-amyl alcohol: DMSO=4:1 (v / v) mixed solvent, vinyl palmitate (2.0mmol) was dissolved in 10mL of tert-amyl alcohol, and then packed in Ready-to-use in a 10mL syringe. Lipase Lipozyme TLIM (0.87g) was evenly filled in the reaction channel of the microfluidic channel reactor, driven by the PHD2000 syringe pump, the two reaction solutions were respectively injected at 10.4 μL min -1 The flow rate enters the reaction channel through the "Y" joint for reaction, and the temperature of the reactor is controlled at 52°C by a water bath thermostat. The reaction solution flows continuously in the reaction channel for 30 minutes, and the reaction results are tracked and detected by thin-layer chromatography (TLC).

[0029] The reaction solution was collected online by the product collector, the solvent was distilled off under reduced pressure...

Embodiment 2-6

[0033] Change the temperature of the microfluidic channel reactor, others are the same as in Example 1, and the reaction results are as shown in Table 1:

[0034] Table 1: Effect of Temperature on Reaction

[0035]

[0036] The results in Table 1 show that when the flow rate is 10.4μLmin -1 , when the reaction time is 30min, the conversion rate increases obviously with the increase of the reaction temperature. When the reaction temperature reaches 52°C, the conversion rate and selectivity of the reaction are the best. The decrease in enzyme activity leads to a decrease in the selectivity of the reaction, so the optimal reaction temperature of mannose palmitate in the microfluidic microchannel reactor of the present invention is 52°C.

Embodiment 6-10

[0038] Change the substrate molar ratio of vinyl palmitate and mannose in the microfluidic microchannel reactor to be 3: 1 (Example 6), 4: 1 (Example 7), 6: 1 (Example 8), 7 : 1 (embodiment 9), 8: 1 (embodiment 10), others are the same as embodiment 1, and the results are shown in table 2.

[0039] Table 2: Effect of mannose to vinyl palmitate substrate ratio on the reaction

[0040]

[0041]

[0042] The result of table 2 shows, along with the increase of reactant vinyl palmitate, the conversion rate of reaction also thereupon increases, and when substrate ratio is 5: 1, mannose is converted into mannose-6-palmitic acid mono ester, and the selectivity of the reaction is also very high, almost no other mannose esters are formed. Now if continue to increase the consumption of reactant vinyl palmitate, it will cause the conversion rate and selectivity of reaction to reduce instead. Therefore, the optimal substrate ratio for the reaction of the present invention is 5:1, u...

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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 [0001] The invention relates to a method for synthesizing mannose-6-palmitate on-line with controllable selectivity catalyzed by lipase. (2) Background technology [0002] Sugar ester is an excellent non-ionic surfactant, which uses natural renewable resource sugar widely existing in nature as raw material, and has broad development prospects. Today's surfactant industry is developing in the direction of green chemistry, which gradually requires non-toxic products, regenerated reaction raw materials, and green reaction processes. As an excellent natural surfactant, sugar esters meet the two requirements of green chemistry: non-toxic products and renewable raw materials, but the reaction process still needs to be further green. [0003] At present, the sugar esters commercially produced at home and abroad are all synthesized by chemical methods, which have many shortcomings, mainly including: the conditions in the reaction process are severe, side reactio...

Claims

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Application Information

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IPC IPC(8): C12P19/02C12M1/00
Inventor 罗锡平杜理华何锋罗宏张航诚顾生妹
Owner ZHEJIANG UNIV OF TECH
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