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Method for catalyzing online synthesis of S-benzyl thiol laurate via lipase

A technology of thiolaurate and vinyl laurate, which is applied in the field of online synthesis of S-benzyl laurate thioester by lipase catalysis, can solve the problems of long reaction time, unsatisfactory conversion rate and high reaction cost, and achieve reduction Effects of reaction cost, high conversion rate and selectivity, and shortened reaction time

Active Publication Date: 2018-05-04
ZHEJIANG FORESTRY UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] So far, there are relatively few studies on enzyme-catalyzed synthesis of thioesters, and the synthesis of enzymatic thioesters mostly uses acylases. This method requires a long reaction time (48h) and is sensitive to specific substrates. The conversion rate is not particularly ideal, and the reaction cost is relatively high

Method used

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  • Method for catalyzing online synthesis of S-benzyl thiol laurate via lipase
  • Method for catalyzing online synthesis of S-benzyl thiol laurate via lipase
  • Method for catalyzing online synthesis of S-benzyl thiol laurate via lipase

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Embodiment 1: the synthesis of S-benzyl laurate thioester

[0028]

[0029] device reference figure 1 : Dissolve benzyl mercaptan (1.0mmol) in 10mL DMSO, vinyl laurate (2.0mmol) in 10mL DMSO, and then put them in 10mL syringes respectively; 0.87g lipase LipozymeTL IM is evenly filled in the reaction channel , driven by the PHD2000 syringe pump, the two reaction solutions were separated at 10.4μL·min -1 The flow rate enters the reaction channel through the "Y" joint for reaction, and the temperature of the reactor is controlled at 50 ° 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.

[0030] The reaction solution was collected online by the product collector, the solvent was removed by distillation under reduced pressure, and the column was wet-packed with 200-300 mesh silica gel. The elution reagent was petroleum ether:et...

Embodiment 2-6

[0034] Change the ratio of the amount of benzyl mercaptan to the substrate substance of vinyl laurate in the microfluidic microchannel reactor, control the temperature at 50°C, and the others are the same as in Example 1. The results are shown in Table 1:

[0035] Table 1: Effect of the ratio of the amount of benzyl mercaptan and vinyl laurate substrate substance on the reaction

[0036]

[0037]

[0038] The results in Table 1 show that when the flow rate is 10.4 μL min -1 , the reaction time is 30min, and the reaction temperature is 50°C. The reactor uses DMSO as the organic solvent. With the increase of the reactant vinyl laurate, the conversion rate of the reaction also increases. When it is 1:2 with vinyl laurate, the conversion rate of the reaction is optimal, so the ratio of the amount of the optimal substrate substance in the microfluidic microchannel reactor in the present invention is 1:2.

Embodiment 7-10

[0040] 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 2:

[0041] Table 2: Effect of Temperature on Reaction

[0042] Example

[0043] The results in Table 2 show that when the flow rate is 10.4 μL min -1 , the reaction time is 30min, the reactor uses DMSO as the organic solvent, and the ratio of the amount of reactant benzyl mercaptan to vinyl laurate is 1:2. When the reaction temperature is at 50°C, the conversion rate of the reaction is the highest Optimum, the temperature is too high or too low will affect the activity of the enzyme. Therefore, the optimum temperature in the microfluidic microchannel reactor in the present invention is 50°C.

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Abstract

The invention discloses a method for catalyzing online synthesis of S-benzyl thiol laurate via lipase. The method comprises the following steps: with dimethyl sulfoxide as a reaction solvent, benzyl mercaptan and vinyl laurate at the molar rate of 1: (0.5-6) as raw materials and the lipase LipozymeTL IM as a catalyst, adding the raw materials and the reaction solvent to an injector, uniformly filling a reaction channel of a micro-fluidic channel reactor with the lipase LipozymeTL IM, continuously supplying the raw materials and the reaction solvent into the reaction channel under the pushing of an injection pumpa and implementing an acylation reaction, wherein the inner diameter of the reaction channel of the micro-fluidic channel reactor is 0.8-2.4mm and the reaction channel is 0.5-1.0m long; and controlling the temperature of the acylation reaction at 20-60 DEG C and the duration of the acylation reaction as 20-40min, collecting a reaction solution online by virtue of a product collector, and conducting conventional treatment on the reaction solution, so that the S-benzyl thiol laurate is obtained. The method provided by the invention has the advantages of being short in reactiontime, high in selectivity and high in yield.

Description

(1) Technical field [0001] The invention relates to a lipase-catalyzed method for synthesizing S-benzyl lauric acid thioester on-line. (2) Background technology [0002] Many synthetic or natural sulfur-containing organic compounds are biologically active. Thioester compounds have pharmacological activities such as antioxidant, antibacterial, and antitumor due to their unique chemical structures, and are important intermediates in organic synthesis and chemical biology. At the same time, the thioester structure also has the function of protecting the unstable thiol functional group, increasing its drug activity, covering the smell of the SH bond, and is widely used in the food, medicine, pesticide and cosmetic industries. [0003] The synthesis of thioesters generally adopts the esterification method. This method mainly uses strong acids such as sulfuric acid and benzenesulfonic acid as catalysts. Such catalysts are highly corrosive, require harsh equipment, and cause serio...

Claims

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Application Information

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IPC IPC(8): C12P11/00C12M1/40C12M1/00
CPCC12M21/18C12M23/16C12M33/04C12M41/22C12P7/6436C12P11/00
Inventor 罗锡平杜理华沈乐
Owner ZHEJIANG FORESTRY UNIVERSITY
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