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Method for online enzymatic synthesis of coumarin-3-carboxylic acid-6'-O-D-sucrose ester derivative based on flow chemistry

A technology of enzymatic synthesis and flow chemistry, applied in chemical instruments and methods, biochemical equipment and methods, chemical/physical processes, etc., can solve problems such as long reaction time, reduce reaction cost, shorten reaction time, and achieve high conversion Rate and selectivity effects

Active Publication Date: 2020-07-28
ZHEJIANG FORESTRY UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Enzyme-catalyzed reactions are relatively mild and green, but require long reaction times (often as long as 24 hours or more) to achieve desired results, and some reactions rely on expensive enzymes

Method used

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  • Method for online enzymatic synthesis of coumarin-3-carboxylic acid-6'-O-D-sucrose ester derivative based on flow chemistry
  • Method for online enzymatic synthesis of coumarin-3-carboxylic acid-6'-O-D-sucrose ester derivative based on flow chemistry
  • Method for online enzymatic synthesis of coumarin-3-carboxylic acid-6'-O-D-sucrose ester derivative based on flow chemistry

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Example 1: Synthesis of 6-methylcoumarin-3-carboxylic acid-6'-O-D-sucrose ester

[0028]

[0029] device reference figure 1 : Methyl 6-methylcoumarin-3-carboxylate (2.0mmol) was dissolved in 0.52mL dimethyl sulfoxide and 9.48mL tert-amyl alcohol, D-sucrose (0.5mmol) was dissolved in 0.52mL dimethyl Base sulfoxide and 9.48mL tert-amyl alcohol, and then put them in 10mL syringes for use. 0.87g of lipase Lipozyme RM IM was evenly filled in the reaction channel, driven by the PHD2000 syringe pump, the two reaction solutions were separated at 7.8 μL min -1The flow rate enters the reaction channel through the "Y" joint for reaction, and the temperature of the reactor is controlled at 35°C by a water bath thermostat. The reaction solution flows continuously in the reaction channel for 40 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 wa...

Embodiment 2-8

[0035] Change the volume ratio of the reaction medium DMSO and tert-amyl alcohol in the microfluidic channel reactor, the substrate ratio of 6-methylcoumarin-3-carboxylate and D-sucrose is 2:1 (1.0mmol:0.5 mmol), the control temperature is 50 DEG C, and the reaction times 30min, other are with embodiment 1, and reaction result is as shown in table 1:

[0036] Table 1: Effect of the volume ratio of DMSO to tert-amyl alcohol in the reaction medium on the reaction

[0037] Example DMSO: tert-amyl alcohol Conversion rate[%] selectivity [%] 2 1:8 n.d. / 3 1:10 15％ / 4 1:12 20％ 98％ 5 1:14 24％ 99％ 6 1:16 29％ 99％ 7 1:18 32％ 99％ 8 1:20 31％ 99％

[0038] The results in Table 1 show that when the substrate molar ratio of the reactant 6-methylcoumarin-3-carboxylate to D-sucrose is 2:1, the flow rate is 10.4 μL min -1 , the reaction time is 30min, and the reaction temperature is 50°C, as the volume ratio of tert-amyl alc...

Embodiment 9-15

[0040] Change the substrate molar ratio of 6-methylcoumarin-3-carboxylate methyl ester to D-sucrose in the microfluidic microchannel reactor, control the temperature of the reactor at 50° C., and the reaction time for 30 minutes. Others are the same as in Example 1 , the results are shown in Table 2:

[0041] Table 2: The influence of the ratio of the amount of 6-methylcoumarin-3-carboxylate methyl ester and D-sucrose substrate substance on the reaction

[0042]

[0043]

[0044] The results in Table 2 show that the volume ratio of the reaction medium DMSO to tert-amyl alcohol is 1:18, and the flow rate is 10.4 μL min -1 , the reaction time is 30min, and the reaction temperature is 50°C, as the reactant 6-methylcoumarin-3-carboxylate methyl ester increases, the conversion rate of the reaction also increases. When the substrate ratio is When 4:1, the conversion rate of reaction is optimum, if continue to increase the consumption of reactant 6-methylcoumarin-3-carboxylate...

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Abstract

A method for online enzymatic synthesis of a coumarin-3-carboxylic acid-6'-O-D-sucrose ester derivative based on the flow chemistry comprises the steps of: uniformly filling lipase Lipozyme RM IM in areaction channel of a micro-fluidic channel reactor, after respectively dissolving a coumarin-3-methyl carboxylate derivative and D-saccharose by using a reactive solvent, respectively injecting intoa pipeline to gather through a first injector and a second injector, performing reaction by entering the reaction channel, and controlling the reaction temperature at 30-60 DEG C, wherein the continuous flow reaction time of the mixed liquid in the reaction channel is 10-60 min; the reaction liquid flowing out of the reaction channel is collected online through a product collector; and thus, thecoumarin-3-carboxylic acid-6'-O-D-sucrose ester derivative is obtained through aftertreatment. The method has the advantages of being short in reaction time, high in productivity and good in selectivity.

Description

technical field [0001] The invention relates to a method for enzymatically synthesizing coumarin-3-carboxylic acid-6'-O-D-sucrose ester derivatives online based on flow chemistry. Background technique [0002] Coumarin is a basic structural subunit in a variety of plant secondary metabolites and microbial metabolites, and has a series of attractive biological activities, including antibacterial, anticoagulant, antiviral, antituberculous, antioxidant and antitumor activity. Several natural and synthetic drugs containing coumarin scaffolds have been clinically applied, such as warfarin as an anticoagulant of vitamin K antagonists, which has been widely used in the treatment of thrombosis. Both contain coumarin substructural units. In addition, due to the parent structure of coumarin, it is widely used in the fields of specific fluorescent probes, dyes, and fluorescent imaging. Among them, the synthesis of sugar-branched coumarin derivatives has attracted considerable attent...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C12P19/60C12M1/40C12M1/02C12M1/00B01J19/00
CPCC12P19/605C12M21/18C12M23/16C12M23/40C12M29/00C12M41/22B01J19/0093Y02P20/55
Inventor 罗锡平杜理华陈平峰
Owner ZHEJIANG FORESTRY UNIVERSITY
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