Method for on-line synthesizing glucose-6-palmitate by lipase catalysis

A technology of palmitate and glucose, which is applied in the field of lipase-catalyzed online controllable selective synthesis of glucose-6-palmitate, which can solve the problems of low conversion rate and selectivity, long reaction time, etc., and shorten the reaction time , reduced usage, high conversion and reaction selectivity

Active Publication Date: 2013-07-03

ZHEJIANG UNIV OF TECH

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AI-Extracted Technical Summary

Problems solved by technology

[0009] At present, many domestic and foreign scholars have studied the enzyme-catalyzed synthesis of glucose esters in organic media, but this method often requires a long reaction time (24h), and the conversion rate and selectivity of the reaction are...

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Abstract

The invention provides a method for on-line synthesizing glucose-6-palmitate by lipase catalysis, comprising: using glucose and vinyl palmitate, with a mol ratio of 1:3-8, as raw materials, using 0.5-10g of Lipozyme TLIM as a catalyst, and using a mixed solvent of tertiary amyl alcohol and DMSO as a reaction solvent, uniformly filling Lipozyme TLIM in a reaction channel of a microfluidic channel reactor, wherein the internal diameter of the reaction channel of the microfluidic channel reactor is 0.8-2.4mm, and the length of the reaction channel is 0.5-1.0m; continuously introducing the raw materials and the reaction solvent into the reaction channel to perform acylation reaction under 40-55 DEG C for 15-35min, on-line collecting the reaction solution, and then obtaining the glucose-6-palmitate after conventional post-treatment on the reaction solution. The method of the invention has advantages of short reaction time, high selectivity and high yield.

Application Domain

Fermentation

Technology Topic

Microfluidic channelHigh selectivity +8

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Examples

Experimental program(4)

Example Embodiment

[0027] Example 1: Synthesis of glucose-6-palmitate

[0028]

[0029] Device reference figure 1 : Dissolve glucose (0.4mmol) in a mixed solvent of 10mL tert-amyl alcohol: DMSO=4:1 (v/v), and dissolve vinyl palmitate (2.0mmol) in 10mL tert-amyl alcohol, and then put them in 10mL separately Reserve in the syringe. 0.87g lipase Lipozyme TLIM is evenly filled in the reaction channel. Driven by the PHD2000 syringe pump, the two reaction solutions are respectively 10.4μL·min -1 The flow rate of the reactor enters the reaction channel through the "Y" connector for reaction. The temperature of the reactor is controlled at 52°C through a water bath thermostat. The reaction liquid flows continuously in the reaction channel for 30 minutes. The reaction result is tracked and detected by thin layer chromatography TLC.

[0030] Collect the reaction liquid online through the product collector, remove the solvent by distillation under reduced pressure, and pack the column with 200-300 mesh silica gel wet method. The elution reagent is chloroform:methanol=10:1, the column height is 35cm, the column diameter is 4.5cm, and a small amount of sample is used. After the elution reagent is dissolved, the column is wetted and the eluate is collected at a flow rate of 2mL·min -1 At the same time, TLC tracked the elution process, combined the obtained eluate containing a single product and evaporated to dryness to obtain white monoester crystals to obtain glucose-6-palmitate. The glucose conversion rate was 98% by HPLC, and glucose-6- The selectivity of palmitate (content of glucose-6-palmitate/total content of produced glucose ester) is 100%.

[0031] The NMR characterization results are as follows:

[0032] 1 H-NMR (DMSO-d6, δ, ppm): Glucose-6-palmitate: 6.36 (d, 1H, J=4.0 Hz, 1-OH of α-D-glucose), 5.06 (d, 1H, J =5.5Hz, H-1 of α-D-glucose), 4.89 (d, 1H, J=5.5Hz, 4-OH of α-D-glucose), 4.77 (d, 1H, J=4.5Hz, α- D-glucose 3-OH), 4.55 (d, 1H, J=7.0 Hz, α-D-glucose 2-OH), 4.27 (d, 1H, J=2.0 Hz, α-D-glucose H- 6), 3.99 (1H, dd, J = 6.3 Hz, J = 11.6 Hz, α-D-glucose H-6'), 3.76 (m, 1H, α-D-glucose H-5), 3.43 ( m, 1H, α-D-glucose H-3), 3.13 (m, 1H, α-D-glucose H-2), 3.04 (m, 1H, α-D-glucose H-4), 2.28 -2.25(m, 2H, a-CH 2 ), 1.52-1.50(t, 2H, J=7.0Hz, β-CH 2 ), 1.25(m, 24H, n-CH 2 ), 0.86(t, 3H, J=7.0Hz, CH 3 ).

Example Embodiment

[0033] Example 2-5

[0034] The temperature of the microfluidic channel reactor was changed, and the others were the same as in Example 1. The reaction results are shown in Table 1:

[0035] Table 1: The influence of temperature on the reaction

[0036]

[0037] The results in Table 1 show that when the flow rate is 10.4μL·min -1 When the reaction time is all 30 minutes, the conversion rate of the reaction increases with the increase of temperature. When the reaction temperature reaches 52℃, the conversion rate and selectivity of the reaction are both the best. At this time, if the temperature is continued to rise, it will cause The decrease in enzyme activity leads to a decrease in the conversion rate and selectivity of the reaction. Therefore, the optimal reaction temperature of glucose palmitate in the microfluidic microchannel reactor of the present invention is 52°C.

Example Embodiment

[0038] Example 6-10

[0039] Change the substrate ratio of vinyl palmitate to glucose in the microfluidic microchannel reactor to 3:1 (Example 6), 4:1 (Example 7), 6:1 (Example 8), 7:1 (Example 9), 8:1 (Example 10), and the others are the same as Example 1. The results are shown in Table 2.

[0040] Table 2: The effect of glucose and vinyl palmitate substrate ratio on the reaction

[0041] Example

[0042] 8

[0043] The results in Table 2 show that as the reactant vinyl palmitate increases, the conversion rate of the reaction also increases. When the substrate ratio is 5:1, the conversion rate and selectivity of the reaction are optimal, and the glucose has basically been quantified. Completely converted to glucose-6-palmitate. At this time, if the amount of reactant vinyl palmitate is increased, the conversion rate and selectivity of the reaction will decrease. Therefore, the optimal substrate ratio of the reaction is 5:1. Under this reaction condition, glucose is basically quantitative Completely converted to glucose-6-palmitate.

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Classification and recommendation of technical efficacy words

Short reaction time
High reaction selectivity and conversion

Rapid microwave-solvothermal synthesis and surface modification of nanostructured phospho-olivine cathodes for lithium ion batteries

InactiveUS20090117020A1Simple preparation procedureShort reaction timePhosphatesCell electrodesSurface modificationOlivine

Owner:BOARD OF RGT THE UNIV OF TEXAS SYST

Method for on-line synthesizing glucose-6-palmitate by lipase catalysis

AI-Extracted Technical Summary

Problems solved by technology

Abstract

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Examples

Example Embodiment

Example Embodiment

Example Embodiment

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Description & Claims & Application Information

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