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Method for synthesizing 6-(benzyl sulfonium)-6-ethylene oxo-hexanoate on line through lipase catalysis

A technology of vinyl hexanoate and lipase, applied in biochemical equipment and methods, methods of sampling biological materials, biochemical instruments, etc., can solve the problems of high reaction cost, unsatisfactory conversion rate, long reaction time, etc. Achieve the effects of shortening reaction time, high conversion rate and selectivity, and reducing reaction cost

Inactive Publication Date: 2018-05-22
ZHEJIANG UNIV OF TECH
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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 synthesizing 6-(benzyl sulfonium)-6-ethylene oxo-hexanoate on line through lipase catalysis
  • Method for synthesizing 6-(benzyl sulfonium)-6-ethylene oxo-hexanoate on line through lipase catalysis
  • Method for synthesizing 6-(benzyl sulfonium)-6-ethylene oxo-hexanoate on line through lipase catalysis

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Example 1: Synthesis of 6-(benzylthio)-6-oxo-hexanoic acid vinyl ester

[0032]

[0033] device reference figure 1 : Benzyl mercaptan (1.0mmol) was dissolved in 10mL DMSO, and divinyl adipate (2.0mmol) was dissolved in 10mL DMSO, and then respectively filled in 10mL syringes for use. 0.87g of lipase LipozymeTL IM was evenly filled in the reaction channel, driven by the PHD2000 syringe pump, the two reaction solutions were separated 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 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.

[0034] Collect the reaction solution online by the product collector, remove the solvent by distillation under reduced pressure, use 200-300 mesh silica gel wet packing column, elution reagent is ...

Embodiment 2-5

[0038] Based on the amount of benzyl mercaptan, change the ratio of the amount of benzyl mercaptan to the substrate substance of divinyl adipate in the microfluidic microchannel reactor, control the temperature at 50°C, and others are the same as in Example 1. The results are shown in Table 1:

[0039] Table 1: The impact of the ratio of the amount of benzyl mercaptan and divinyl adipate substrate substance on the reaction

[0040] Example

[0041] 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 divinyl adipate, the conversion rate of the reaction also increases. When the ratio of mercaptan and divinyl adipate is 1:2, 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 6-9

[0043] Change the temperature of the microfluidic channel reactor, the others are the same as in Example 1, and the reaction results are shown in Table 2:

[0044] Table 2: Effect of Temperature on Reaction

[0045]

[0046]

[0047] 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 the reactant benzyl mercaptan to divinyl adipate is 1:2. When the reaction temperature is at 50°C, the conversion of the reaction The optimum rate, 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 synthesizing 6-(benzyl sulfonium)-6-ethylene oxo-hexanoate on line through lipase catalysis. The method comprises the following steps: by taking dimethyl sulfoxideas a reaction solvent, taking benzyl mercaptan and divinyl adipate as raw materials according to a mole ratio of 1: (0.5 to 6), and taking lipase Lipozyme TL IM as a catalyst, placing the raw materials and the reaction solvent into an injector, uniformly filling a reaction channel of a microfluidic channel reactor with the lipase Lipozyme TL IM, and continuously feeding the raw materials and thereaction solvent into the channel reactor for acylation reaction under pushing of an injection pump, wherein the inner diameter of the reaction channel of the microfluidic channel reactor is 0.8 to 2.4 mm, and the reaction channel is 0.5 to 1.0 m in length; controlling the acylation reaction temperature at 20 to 60 DEG C and the acylation reaction time for 20 to 40 min, collecting reaction liquidon line through a product collector, and treating the reaction liquid in a conventional way to obtain the 6-(benzyl sulfonium)-6-ethylene oxo-hexanoate. The method has the advantages of short reactiontime, high selectivity and high yield.

Description

technical field [0001] The invention relates to a lipase-catalyzed online synthesis method of 6-(benzylthio)-6-oxohexanoic acid vinyl ester. Background technique [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 seri...

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 杜理华董振罗锡平沈乐欧志敏张文
Owner ZHEJIANG UNIV OF TECH
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