Method of applying immobilized lipase to catalyze ester hydrolysis for kinetic resolution of 2-(4-methylphenyl) propionic acid enantiomers

A lipase-catalyzed ester and immobilized lipase technology, applied in the direction of immobilized enzymes, biochemical equipment and methods, fixed on/in organic carriers, etc., can solve the problems of low loading rate and mass transfer performance of immobilized enzymes Poor quality, short service life of polymer materials, etc., to achieve enhanced stability and operating range, easy separation, and good reusability

Inactive Publication Date: 2020-06-30
HUNAN INSTITUTE OF SCIENCE AND TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Polymer materials have shortcomings such as short service life and poor mass transfer performance; inorganic carriers have the advantages of good stability, low cost, and long life, but the loading rate of immobilized enzymes prepared using inorganic materials is generally low

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0014] Mix 0.01mmol racemic methyl 2-(4-methylphenyl)propionate and 50mg immobilized enzyme AYS@UIO-66-NH 2 Add it into a 10mL reaction tube, and add 2mL of phosphate buffer solution (pH=6.60, 0.1mmoL / L) as the reaction solution, and heat the reaction at 500rpm and 39°C for 24h; The ratio and the enantiomeric excess of the product were analyzed. The analysis results showed that the yield of (R)-2-(4-methylphenyl)propionic acid was 72.567%, and the enantiomeric excess was 93.202%.

Embodiment 2

[0016] 0.01 mmol of racemic 2-(4-methylphenyl) propionate methyl ester and 50 mg of immobilized enzyme AYS@UIO-66-NH 2 Put it into a 10mL reaction tube, and add 2mL of phosphate buffer solution (pH=6.60, 0.1mmoL / L) as the reaction solution, and catalyze the reaction at a rotation speed of 500rpm and a reaction temperature of 60°C for 24h. After the reaction, use high-performance liquid chromatography Yield and product enantiomeric excess were analyzed by instrument. The analysis results showed that the yield of (R)-2-(4-methylphenyl)propionic acid remained at 70.458%, and the enantiomeric excess was 91.789%.

Embodiment 3

[0018] 0.01 mmol of racemic 2-(4-methylphenyl) propionate methyl ester and 50 mg of immobilized enzyme AYS@UIO-66-NH 2 Put it into a 10mL reaction tube, and add 2mL of phosphate buffer solution (0.1mmoL / L), the pH value is 8.5, as the reaction solution, catalyze the reaction at a rotation speed of 500rpm and a reaction temperature of 39°C for 24h. Chromatography was used to analyze the yield and enantiomeric excess of the product. The analysis results showed that the yield of (R)-2-(4-methylphenyl)propionic acid remained at 70.023%, and the enantiomeric excess was 90.924%.

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Abstract

The patent discloses a method of applying immobilized lipase to catalyze ester hydrolysis for kinetic resolution of 2-(4-methylphenyl) propionic acid enantiomers. A bifunctional compound glutaraldehyde is used to react with a carrier UIO-66-NH2 and an amino group on candida rugosa lipase (Lipase AYS) at the same time to form a Schiff base to realize a covalent link of the enzyme and the carrier toobtain the immobilized enzyme which is used for the kinetic resolution of the 2-(4-methylphenyl) propionic acid enantiomers. Optically pure 2-(4-methylphenyl) propionic acid is an important pharmaceutical intermediate. The provided preparation method has obvious technical advantages. The covalently linked immobilization has stronger binding force, can reduce loss of the enzyme and maintains activity and selectivity of the enzyme. Compared with free enzymes, the immobilized enzyme is high in thermal stability, high in pH tolerance, easy for recycling for use and easy for separation from the product, significantly reduces technical cost, and is also simple in operation, green and environmentally protective.

Description

technical field [0001] The invention belongs to the technical field of biocatalysis, through metal organic framework compound (MOFs) UIO-66-NH 2 A Candida rugosa lipase (Lipase AYS) was immobilized and applied to stereoselectively catalyzed ester hydrolysis for the resolution of 2-(4-methylphenyl)propionic acid enantiomers. Background technique [0002] 2-(4-methylphenyl)propionic acid (2-(4-MP)PPA) is an important pharmaceutical intermediate, mainly used in the production of aryl propionic acid anti-inflammatory drugs (such as loxoprofen) synthesis. Enzymatic stereoselectively catalyzed reactions can directly convert chemically synthesized racemates into single enantiomers. Moreover, as a natural polymer catalyst, enzymes have many advantages such as high stereoselectivity, mild reaction conditions, and no pollution, making them have extremely broad application prospects in food, medicine, fine chemicals and other industrial fields. However, the free enzyme is difficult ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C12P41/00C12P7/40C12N11/089C12N9/20
CPCC12P41/005C12P7/40C12N11/08C12N9/20C12Y301/01003
Inventor 张盼良陈婧唐课文孙碧珠孙晨蕊许卫凤
Owner HUNAN INSTITUTE OF SCIENCE AND TECHNOLOGY
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