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A kind of lipase-catalyzed method for synthesizing s-benzyl palmitic acid thioester on-line

A technology of benzyl palmitic acid thioester and vinyl palmitate, which is applied in the field of online synthesis of S-benzyl palmitic acid thioester by lipase catalysis, can solve the problems of long reaction time, high reaction cost, and unsatisfactory conversion rate, etc. , to achieve the effects of reducing reaction cost, shortening reaction time, high conversion rate and selectivity

Active Publication Date: 2021-06-08
ZHEJIANG FORESTRY UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] 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 the conversion rate for specific substrate reactions is not high. Especially ideal, and the reaction cost is relatively high

Method used

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  • A kind of lipase-catalyzed method for synthesizing s-benzyl palmitic acid thioester on-line
  • A kind of lipase-catalyzed method for synthesizing s-benzyl palmitic acid thioester on-line
  • A kind of lipase-catalyzed method for synthesizing s-benzyl palmitic acid thioester on-line

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Embodiment 1: the synthesis of S-benzyl palmitic acid thioester

[0033]

[0034] device reference figure 1 : Dissolve benzyl mercaptan (1.0mmol) in 10mL DMSO, vinyl palmitate (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).

[0035]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 e...

Embodiment 2-6

[0039] Change the ratio of the amount of benzyl mercaptan to the substrate substance of vinyl palmitate 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:

[0040] Table 1: Effect of the ratio of the amount of benzyl mercaptan and vinyl palmitate substrate substance on the reaction

[0041] Example Benzyl Mercaptan:Vinyl Palmitate Conversion rates[%] selectivity [%] 2 1:0.5 25 95 3 1:1 61 95 1 1:2 85 96 4 1:3 79 96 5 1:4 73 94 6 1:5 70 97

[0042] 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 palmitate, the conversion rate of the reaction also increases. When the substrate is more than benzyl mercaptan When it is 1:2 with vinyl palmitate, ...

Embodiment 7-10

[0044] 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:

[0045] Table 2: Effect of Temperature on Reaction

[0046] Example temperature[°C] Conversion rates[%] selectivity [%] 7 40 60 95 8 45 76 97 1 50 85 96 9 55 80 96 10 60 75 97

[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 an organic solvent, the ratio of the amount of reactant benzyl mercaptan to vinyl palmitate is 1:2, and the concentration of benzyl mercaptan in the reaction system is 0.05mmol / When the reaction temperature is 50 °C, the conversion rate of the reaction is the best, and the temperature will affect the activity of the enzyme if it is too high or too low. 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 lipase-catalyzed method for synthesizing S-benzyl palmitic acid thioester on-line: using dimethyl sulfoxide as a reaction solvent, and using benzyl mercaptan and vinyl palmitate at a molar ratio of 1:0.5-6 As the raw material, lipase Lipozyme TL IM is used as the catalyst, the raw material and the reaction solvent are placed in the syringe, the lipase Lipozyme TL IM is evenly filled in the reaction channel of the microfluidic channel reactor, and the raw material is driven by the syringe pump. and the reaction solvent are continuously passed into the reaction channel device to carry out the acylation reaction. The inner 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; the temperature of the acylation reaction is controlled to be 20-2. 60°C, the acylation reaction time is 20-40min, the reaction solution is collected online by the product collector, and the reaction solution is subjected to conventional post-treatment to obtain S-benzyl palmitic acid thioester. The invention has the advantages of short reaction time, high selectivity and high yield.

Description

[0001] (1) Technical field [0002] The invention relates to a lipase-catalyzed method for synthesizing S-benzyl palmitic acid thioester on-line. [0003] (2) Background technology [0004] 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. [0005] 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...

Claims

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Application Information

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Patent Type & Authority Patents(China)
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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