Method for stereoselective enzymatic hydrolysis to resolve 2-(3-chlorophenyl)propionic acid enantiomers

A stereoselective, catalytic hydrolysis technology, applied in the direction of fermentation, etc., can solve the problems of low conversion rate and low solubility, and achieve the effects of improving conversion rate, mild reaction conditions and overcoming toxicity

Active Publication Date: 2018-07-06
HUNAN INSTITUTE OF SCIENCE AND TECHNOLOGY
View PDF7 Cites 7 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

And aiming at the low solubility of the enzyme-catalyzed resolution substrate in the water phase medium, resulting in a low conversion rate, by adding a surfactant, the dispersion of the substrate in the water phase medium is promoted, thereby increasing the conversion rate

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Method for stereoselective enzymatic hydrolysis to resolve 2-(3-chlorophenyl)propionic acid enantiomers
  • Method for stereoselective enzymatic hydrolysis to resolve 2-(3-chlorophenyl)propionic acid enantiomers
  • Method for stereoselective enzymatic hydrolysis to resolve 2-(3-chlorophenyl)propionic acid enantiomers

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Put 0.020 mmol of racemic heptyl 2-(3-chlorophenyl)propionate in a 25 mL reaction tube, and use 1 mL of disodium hydrogen phosphate / phosphate buffer solution (pH = 5.5) as the reaction medium, respectively Add 20 mg of different commercial lipases and react for 16 h at 600 rpm and 50 °C. After the reaction, the product was filtered and analyzed by high performance liquid chromatography. The results show that: when Pseudomonas cepacia lipase is used as a catalyst, it preferentially recognizes ( R )-2-(3-chlorophenyl) heptyl propionate, its ee p 98.16%, c was 11.09%.

Embodiment 2

[0028] Put 0.020 mmol of different kinds of racemic 2-(3-chlorophenyl)propionate in a 25 mL reaction tube, and use 1 mL of disodium hydrogen phosphate / phosphate buffer solution (pH = 5.5) as the reaction medium, Add 20 mg of Pseudomonas cepacia lipase and react for 15 h at 600 rpm and 40 °C. After the reaction, the product was filtered and analyzed by high performance liquid chromatography. The results show that: when the substrate is 2-(3-chlorophenyl) heptyl propionate, its ee p 98.20%, c was 7.26%.

Embodiment 3

[0030] Put 0.020 mmol of racemic heptyl 2-(3-chlorophenyl)propionate in a 25 mL reaction tube, use 1 mL of disodium hydrogen phosphate / phosphate buffer solution (pH = 5.5) as the reaction medium, add 20 mg of Pseudomonas cepacia lipase was reacted for 4 h at 600 rpm and 70 °C. After the reaction, the product was filtered and analyzed by high performance liquid chromatography. The results show that: its ee p 98.82%, c was 10.31%.

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

PUM

No PUM Login to view more

Abstract

The present invention describes a method for lipase kinetic resolution of 2-(3-chlorophenyl)propionic acid enantiomers. By use of efficient selective lipase, racemic 2-(3-chlorophenyl)propionate is catalytically hydrolyzed in an aqueous medium to resolve 2-(3-chlorophenyl)propionic acid. Through addition of surfactant PEG400 to the reaction system, the substrate conversion rate is greatly increased. The optical purity of the product is >=97%, and the conversion rate is >=40%. Compared with other resolution technologies, the method has mild reaction conditions, simple operation and low environmental pollution, and provides a feasible method for the production of (S)-Pirprofen in the pharmaceutical industry.

Description

technical field [0001] The invention belongs to the technical field of biocatalysis, in particular to a method for splitting 2-(3-chlorophenyl)propionic acid through lipase stereoselective catalytic hydrolysis. Background technique [0002] According to the United States "Time Magazine" and "Medical Annals", ibuprofen, which is favored by consumers, can cause adverse reactions such as indigestion, stomach burning, stomach pain and vomiting, and long-term use can cause renal failure. Picloprofen, as a derivative of ibuprofen, is also an important non-steroidal anti-inflammatory drug, which has significant anti-rheumatic, analgesic, anti-inflammatory and antipyretic effects. Clinical studies have shown that picloprofen has inhibitory effects on leukocyte chemotaxis, platelet adhesion and aggregation. Its analgesic effect is 10 times stronger than that of salicylic acid drugs, and it can significantly improve some typical symptoms such as pain at rest and during exercise, morn...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

Application Information

Patent Timeline
no application Login to view more
Patent Type & Authority Applications(China)
IPC IPC(8): C12P41/00C12P7/40C12P7/62
CPCC12P7/40C12P7/62C12P41/001
Inventor 唐课文张盼良成晴许卫凤
Owner HUNAN INSTITUTE OF SCIENCE AND TECHNOLOGY
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap