Method for preparing methylbutylamine p-benzoquinone through lipase catalysis

A technology for the catalytic preparation of methylbutylamine, applied in biochemical equipment and methods, enzymes, hydrolytic enzymes, etc., can solve the problems of high separation cost, difficult separation and purification, and low yield

Inactive Publication Date: 2018-10-19
QINGDAO UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The above-mentioned multiple products will form a mixture, and the separation and purification of multiple products is

Method used

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  • Method for preparing methylbutylamine p-benzoquinone through lipase catalysis

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Experimental program
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Effect test

Embodiment 1

[0014] 10ml brown reaction bottle, stir with magnet, add 2ml of citric acid buffer solution with pH 7.0, which contains 3-5% methanol, methyl-p-benzoquinone and butylamine are fed in equimolar ratios, the concentration of butylamine is 0.05-0.1mM, Add immobilized Candida antarctica lipase B, Novozme 435, the amount of enzyme added is 5-10U / mL, the reaction temperature is 38-42°C, and N 2 After 3 minutes, seal the bottle cap and start the reaction, the reaction time is 20-24h. After the reaction was finished, samples were taken for liquid chromatography analysis, and the liquid phase detection results: the reaction conversion rate was 99-100%, the product 2-methyl-5-butylamine p-benzoquinone yield was 94-95%, and other substituted products produced The rate is less than 2.5%.

[0015] Liquid phase detection conditions: Agilent 1200 liquid chromatograph, C18 reverse phase column, 250mm, mobile phase: methanol / water=80 / 20, product 2-methyl-5-butylamine-p-benzoquinone retention ...

Embodiment 2

[0017] 100ml brown reaction bottle, stir with magnet, add 20ml of citric acid buffer solution with pH 7.0, which contains 3-5% methanol, methyl p-benzoquinone and butylamine are fed in equimolar ratios, the concentration of butylamine is 0.05-0.1mM, Add immobilized Candida antarctica lipase B, Novozme 435, the amount of enzyme added is 5-10U / mL, the reaction temperature is 38-42°C, and N 2 After 5 minutes, close the bottle cap and start the reaction, the reaction time is 20-24h. After the reaction, take a sample for liquid chromatography analysis, filter out the immobilized enzyme, and the immobilized enzyme can be reused. The filtrate was extracted with acetone, the organic phase was separated, and the acetone was evaporated to obtain the product 2-methyl-5-butylamino-p-benzoquinone. The liquid phase detection results: the reaction conversion rate was 99-100%, and the product 2-methyl-5- The yield of butylamine-p-benzoquinone is 94-95%, and the yield of other substituted pr...

Embodiment 3

[0020] 1000ml brown reaction bottle, stir with magnet, add 500ml of citric acid buffer solution with pH 7.0, which contains 3% methanol, methyl-p-benzoquinone and butylamine are fed equimolarly, the concentration of butylamine is 0.05mM, add immobilized Antarctic Candida lipase B, Novozme 435, enzyme dosage 5U / mL, reaction temperature 42°C, N 2 After 15 minutes, seal the bottle cap and start the reaction, the reaction time is 20h. After the reaction, take a sample for liquid chromatography analysis, filter out the immobilized enzyme, and the immobilized enzyme can be reused. The filtrate was extracted with acetone, the organic phase was separated, and the acetone was evaporated to obtain the product 2-methyl-5-butylamine-p-benzoquinone. The liquid phase detection result: the reaction conversion rate was 99%, and the product 2-methyl-5-butylamine The yield of p-benzoquinone was 94%, and the yield of other substituted products was less than 2.5%.

[0021] The detection condit...

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Abstract

The invention discloses a method for preparing methylbutylamine p-benzoquinone through lipase catalysis. The method is characterized by comprising a step of catalyzing butyl amine to react with methylp-benzoquinone by using immobilized candida antarctica lipase, thereby obtaining 2-methyl-5-methylbutylamine p-benzoquinone. The 2-methyl-5-methylbutylamine p-benzoquinone is prepared by using an enzyme catalysis method, because of high spatial selectivity of an enzyme, difficulties that a chemical synthesis process is poor in selectivity and hard in product separation can be avoided, and the method is an environmental-friendly efficient synthesis method.

Description

technical field [0001] The invention belongs to the technical field of pharmaceutical engineering, and in particular relates to the catalytic preparation of antitumor active substance 2-methyl-5-butylamino-p-benzoquinone by using C. antarctica lipase B. Background technique [0002] 2-Methyl-5-butylamine-p-benzoquinone has strong antitumor activity, and it is expected to be able to fight against tumors in various parts, and has been developed as an antitumor drug with wide application. From the structural point of view, it is mainly two effective groups of benzoquinone and amine that make it have anti-tumor activity. [0003] Synthesis of 2-methyl-5-butylamine p-benzoquinone by chemical method will produce 3- and 6-substituted butylamine products instead of only 5-substituted butylamine products due to poor steric selectivity. The following differences may be obtained Substituted products: (1) 3,5 substituted dibutylamine products, (2) 3,5,6 substituted tributylamine produc...

Claims

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Application Information

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IPC IPC(8): C12P13/00C12N9/20C12N11/00
CPCC12N9/20C12N11/00C12P13/001
Inventor 唐慧吕奎营赵秋香孙杨建任文杰赵嘉凯张媛媛杨丰科
Owner QINGDAO UNIV OF SCI & TECH
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