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Method for on-line synthesis of coumarin-3-carboxylic acid sugar ester derivative based on flow chemistry enzymatic catalysis

A technology of flow chemistry and carboxylate sugar ester is applied in the field of enzymatic online synthesis of coumarin-3-carboxylate sugar ester derivatives based on flow chemistry, which can solve problems such as long reaction time, reduce reaction cost and shorten reaction time. Effects of time, high conversion and selectivity

Active Publication Date: 2020-08-21
ZHEJIANG UNIV OF TECH
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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 on-line synthesis of coumarin-3-carboxylic acid sugar ester derivative based on flow chemistry enzymatic catalysis
  • Method for on-line synthesis of coumarin-3-carboxylic acid sugar ester derivative based on flow chemistry enzymatic catalysis
  • Method for on-line synthesis of coumarin-3-carboxylic acid sugar ester derivative based on flow chemistry enzymatic catalysis

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Embodiment 1: the synthesis of coumarin-3-carboxylic acid-6'-O-D-glucose ester

[0029]

[0030] device reference figure 1 : Methyl coumarin-3-carboxylate (2.0mmol) was dissolved in 0.52mL dimethylsulfoxide and 9.48mL tert-amyl alcohol, D-glucose (0.5mmol) was dissolved in 0.52mL dimethylsulfoxide and 9.48mL of tert-amyl alcohol, and then put them in 10mL syringes for later 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-1 The 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).

[0031] Collect the reaction solution online by the product collector, remove the solvent by distil...

Embodiment 2-8

[0036] Change the volume ratio of reaction medium DMSO and tert-amyl alcohol in the microfluidic channel reactor, the substrate ratio of coumarin-3-carboxylate and D-glucose is 2:1 (1.0mmol: 0.5mmol), control Temperature is 50 ℃, and reaction times 30min, other are with embodiment 1, and reaction result is as shown in table 1:

[0037] The impact of the volume ratio of DMSO and tert-amyl alcohol on the reaction in the reaction medium of table 1

[0038] Example DMSO: tert-amyl alcohol Conversion rates[%] selectivity [%] 2 1:8 n.d. / 3 1:10 15％ 99％ 4 1:12 28％ 99％ 5 1:14 36％ 99％ 6 1:16 43％ 99％ 7 1:18 45％ 99％ 8 1:20 42％ 99％

[0039] The results in Table 1 show that when the substrate molar ratio of the reactant coumarin-3-carboxylate to D-glucose 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 alcohol in the reaction m...

Embodiment 9-15

[0041] Change the substrate molar ratio of coumarin-3-carboxylate methyl ester to D-glucose in the microfluidic microchannel reactor, control the reactor temperature at 50°C, and the reaction time for 30min. Others are the same as in Example 1, and the results are shown in the table 2 shows:

[0042] The impact of the ratio of the amount of table 2 coumarin-3-carboxylate and D-glucose substrate substance on the reaction

[0043] Example Methyl coumarin-3-carboxylate: D-glucose Conversion rates[%] selectivity [%] 9 5:1 60％ 98％ 10 4:1 61％ 99％ 11 3:1 54％ 99％ 12 2:1 45％ 98％ 13 1:1 34％ 98％ 14 1:2 31％ 98％ 15 1:3 23％ 98％

[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 coumarin-3-carboxylate methyl ester increases, the conversion ...

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Abstract

The invention relates to a method for on-line synthesis of coumarin-3-carboxylic acid sugar ester derivatives based on flow chemistry enzymatic catalysis. The method comprises the following steps: uniformly filling a reaction channel of a microfluidic channel reactor with lipase Lipozyme RM IM; respectively dissolving coumarin-3-carboxylic acid methyl ester and a carbohydrate compound by using a reaction solvent; injecting raw materials into a pipeline through a first injector and a second injector respectively and gathering; controlling the reaction temperature to be 30-60 DEG C and the continuous flowing reaction time of a mixed solution in the reaction channel to be 10-60 minutes, collecting a reaction solution flowing out of the reaction channel on line through a product collector, andperforming post-treatment to obtain a coumarin-3-carboxylic acid sugar ester derivative product, the method has the advantages of short reaction time, high yield and good selectivity.

Description

technical field [0001] The invention relates to a method for enzymatically synthesizing coumarin-3-carboxylate sugar ester derivatives on-line 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 attention in organ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C12P19/60C12M1/40C12M1/02C12M1/00
CPCC12P19/605C12M21/18C12M23/16C12M23/40C12M29/00C12M33/04C12M41/14
Inventor 杜理华陈平锋罗锡平薛苗杨梦婕龙瑞杰闫晨宇
Owner ZHEJIANG UNIV OF TECH
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