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Method for splitting 2-phenylpropionic acid enantiomer by catalyzing esterification of Novozym 435 lipase

A technology for phenylpropionic acid and enantiomers, applied in the field of biological separation of chiral compounds, can solve the problems of slow reaction rate, low optical purity of products, low reaction concentration, etc., achieve mild reaction conditions and simple implementation process , the effect of high reaction concentration

Active Publication Date: 2019-02-01
HUNAN INSTITUTE OF SCIENCE AND TECHNOLOGY
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The purpose of the present invention is to propose a method for separating the enantiomers of 2-phenylpropionic acid to obtain a single configuration for the problems of low reaction concentration, slow reaction rate, and low optical purity of the product in other racemate resolution methods. enantiomeric approach

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0014] Add 100 mmol / L 2-phenylpropionic acid and 140 mmol / L n-hexanol, 100 mg Novozym435 lipase into 2 mL n-hexane; heat the reaction at 400 rpm and 50°C in a 25 mL reaction tube 60 min. At this time, the substrate conversion rate was 97.33%, the enantiomer excess value of the remaining 2-phenylpropionic acid enantiomer was 87.41%, and the target enantiomer yield was 5.01%.

Embodiment 2

[0016] Add 100 mmol / L 2-phenylpropionic acid and 200 mmol / L n-hexanol, 300 mg Novozym435 lipase into 2 mL n-hexane organic solvent; in a 25 mL reaction tube at 400 rpm, 50 °C Heat the reaction for 45 min. At this point, the substrate conversion rate was 97.23%, the enantiomer excess value of the remaining 2-phenylpropionic acid enantiomer was 89.20%, and the yield of the target enantiomer was 5.24%.

Embodiment 3

[0018] Add 10 mmol / L 2-phenylpropionic acid, 140 mmol / L n-hexanol, and 60 mg of Novozym435 lipase into 2 mL of n-hexane organic solvent; heat in a 25 mL reaction tube at 400 rpm and 50 °C React for 140 min. At this time, the substrate conversion rate was 86.73%, the enantiomer excess value of the remaining 2-phenylpropionic acid enantiomer was 86.74%, and the yield of the target enantiomer was 24.77%.

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Abstract

The invention relates to a novel chiral splitting method for obtaining an enantiomer of (R)-2-phenylpropionic acid, which belongs to the technical field of biochemical splitting of chiral compounds. By using the stereoselectivity of Novozym 435, the catalytic esterification of a 2-phenylpropionic acid enantiomer in (S)-2-phenylpropionic acid is carried out with high catalytic efficiency to synthesize (S)-2-n-hexyl phenylpropionate, the remaining unreacted substrate is high optical purity (R)-2-phenylpropionic acid, the substrate conversion rate is 97.23%, the enantiomeric excess value is 89.20%, and the target enantiomer yield is 5.24 %. Compared with other methods, the method has the advantages of simple reaction system, high reaction concentration, fast reaction rate, high optical purityof target products, environmental protection, and simple post-treatment.

Description

technical field [0001] The invention belongs to the separation of chiral compounds by biological methods, and is a kind of stereoselective catalytic esterification of racemic 2-phenylpropionic acid enantiomers using immobilized lipase Novozym 435 to obtain single configuration 2-phenylpropionic acid pairs Enantiomer method. Using Novozym 435 lipase to selectively catalyze the esterification of racemic 2-phenylpropionate to single-configuration n-hexyl (S)-2-phenylpropionate to obtain (R)-2- Phenylpropionic acid. Background technique [0002] 2-Phenylpropionic acid (2-Phenylpropionic acid), also known as α-phenylpropionic acid, is the simplest structure of arylpropionic acid substances, and is the intermediate for the synthesis of arylpropionic acid anti-inflammatory analgesics and fine chemical products body, and are widely used in the synthesis of medicines, spices and pesticides. 2-Phenylpropionic acid, as an important drug synthesis intermediate, can be used to synthes...

Claims

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Application Information

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IPC IPC(8): C12P41/00C12P7/40
CPCC12P7/40C12P41/005
Inventor 唐课文张盼良袁欣许卫凤
Owner HUNAN INSTITUTE OF SCIENCE AND TECHNOLOGY
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