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A kind of stereoselective enzyme-catalyzed hydrolysis resolution method for enantiomers of 2-(3-chlorophenyl)propionic acid

A stereoselective, catalytic hydrolysis technology, applied in the direction of fermentation, etc., can solve the problems of low solubility and low conversion rate

Active Publication Date: 2021-10-15
HUNAN INSTITUTE OF SCIENCE AND TECHNOLOGY
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  • Abstract
  • Description
  • Claims
  • Application Information

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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

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  • A kind of stereoselective enzyme-catalyzed hydrolysis resolution method for enantiomers of 2-(3-chlorophenyl)propionic acid
  • A kind of stereoselective enzyme-catalyzed hydrolysis resolution method for enantiomers of 2-(3-chlorophenyl)propionic acid
  • A kind of stereoselective enzyme-catalyzed hydrolysis resolution method for enantiomers of 2-(3-chlorophenyl)propionic acid

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, 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 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 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%.

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Abstract

This patent introduces a method for splitting 2-(3-chlorophenyl)propionic acid enantiomers using lipase kinetics. Using lipase with high efficiency and selectivity, catalyzed hydrolysis of racemic 2-(3-chlorophenyl) propionate in an aqueous medium to resolve 2-(3-chlorophenyl) propionic acid. Adding surfactant PEG400 to the reaction system greatly improved the substrate conversion rate. The optical purity of the product is ≥97%, and the conversion rate is ≥40%. Compared with other splitting technologies, the method has mild reaction conditions, simple operation, little environmental pollution, and is suitable for the production of ( S )-piclobuprofen provides a feasible method.

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

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Application Information

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Patent Type & Authority Patents(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
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