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Method for stereoselective resolution of 2-(4-methylphenyl)propionic acid enantiomer catalyzed by candida rugosa lipase

A Candida rugosa, stereoselective technology, applied in fermentation and other directions, can solve the problems of optical purity and low yield of products separating chiral enantiomers, and achieve high catalytic efficiency, high yield, and reaction conditions mild effect

Inactive Publication Date: 2018-09-14
HUNAN INSTITUTE OF SCIENCE AND TECHNOLOGY
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The present invention aims at the difficult problems such as the optical purity of the chiral enantiomer separated by the general racemic resolution method and the low yield of the product, and proposes a method to obtain a single configuration (+)-2-(4-methylbenzene A method for (+)-propionic acid—synthesis of a single enantiomer (+)-2 using the high selectivity and high catalytic efficiency of Candida rugosa lipase for the 2-(4-methylphenyl)propionate enantiomer -(4-methylphenyl)propionic acid method

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] will be 40×10 -3 Mmol of 2-(4-methylphenyl)propionate enantiomer and 10 mg of Candida rugosa lipase were sequentially added to 2 mL of pH 6 sodium dihydrogen phosphate buffer solution; The reaction tube was heated at 300 rpm and 50 °C for 6 h; the conversion rate of the substrate was 12.40%, and the optical purity of the product was 92.12%.

Embodiment 2

[0020] will be 20×10 -3 Add 1 mmol of 2-(4-methylphenyl)propionate enantiomer and 10 mg of Candida rugosa lipase to 1 mL of pH 6 sodium dihydrogen phosphate buffer solution; in 25 mL of reaction The tube was heated at 300 rpm and the reaction temperature was 40°C for 4 h. At this time, the conversion rate of the substrate was 17.79%, and the optical purity of the product was 94.16%.

Embodiment 3

[0022] will be 20×10 -3 Mmol of 2-(4-methylphenyl)propionate enantiomer and 10 mg of Candida rugosa lipase were added to 1 mL of sodium dihydrogen phosphate buffer solution at pH 6.5; in 25 mL of reaction The reaction was heated in the tube at 300 rpm and 40°C for 4 h; at this time, the conversion rate of the substrate was 20.07%, and the optical purity of the product was 96.72%.

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Abstract

The invention discloses a novel chiral resolution method for obtaining a single enantiomer of 2-(4-methylphenyl)propionic acid, namely a method for synthesizing a single enantiomer of 2-(4-methylphenyl)propionic acid by enzymatically catalyzed stereoselective hydrolysis of 2-(4-methylphenyl)propionate enantiomers. Based on high selectivity and high catalytic efficiency of candida rugosa lipase, 2-(4-methylphenyl)propionate enantiomers are hydrolyzed to obtain (+)-2-(4- methylphenyl)propionic acid with high optical purity; based on the interaction of cyclodextrin to 2-(4-methylphenyl)propionateenantiomers, the conversion rate of 2-(4-methylphenyl)propionate is improved; the conversion rate of a substrate and the optical purity of the product can be as high as 40.76% and 96.24%, respectively, and the stereoselectivity E is as high as 145; the method overcomes the problems of low optical purity, low yield, environmental pollution and the like of general resolution technology, and can achieve high conversion rate and high selectivity of hydrolysis of 2-(4-methylphenyl)propionate enantiomers, so as to realize non-toxic, harmless and environmental-friendly resolution of chiral compoundsand mild reaction conditions; and the aims of simple equipment, easy operation, low cost and the like are achieved.

Description

technical field [0001] The invention belongs to the preparation of chiral compounds by biological methods, and relates to a method of stereoselectively catalyzing the hydrolysis of 2-(4-methylphenyl)propionate enantiomers to synthesize single-configuration 2-( 4-Methylphenyl) propionic acid enantiomer method. Candida rugosa lipase was used to hydrolyze racemic 2-(4-methylphenyl)propionate to synthesize (+)-2-(4-methylphenyl)propionate in a single configuration. Background technique [0002] 2-(4-methylphenyl)propionic acid is a hydrophilic synthetic non-steroidal high-efficiency anti-inflammatory drug intermediate, because it is a drug precursor for the synthesis of loxoprofen sodium. Loxoprofen sodium is a non-steroidal anti-inflammatory drug with good anti-inflammatory effect and few side effects. Compared with other non-steroidal anti-inflammatory drugs (NSAID), it has obvious effect and less toxic effect on gastrointestinal tract and kidney. It has been reported in th...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C12P41/00C12P7/40
CPCC12P7/40C12P41/00
Inventor 唐课文张盼良刘光勇许卫凤
Owner HUNAN INSTITUTE OF SCIENCE AND TECHNOLOGY
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