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Method for preparing (S)-2-phenylbutyric acid by stereoselective enzyme catalytic hydrolysis

A technology of stereoselectivity and phenylbutyric acid, applied in fermentation and other fields, can solve the problems of 2-phenylbutyric acid, such as low optical purity, environmental pollution, complicated operation, etc., and achieve the goal of overcoming toxicity, simple operation, and improving conversion rate Effect

Active Publication Date: 2018-09-18
HUNAN INSTITUTE OF SCIENCE AND TECHNOLOGY
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] The object of the invention is to solve problems such as low optical purity, complex operation, high cost, and environmental pollution of 2-phenylbutyric acid in the prior art, propose a kind of lipase catalyzed hydrolysis splitting 2-phenylbutyrate, obtain Process for high optical purity (S)-2-phenylbutyric acid

Method used

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  • Method for preparing (S)-2-phenylbutyric acid by stereoselective enzyme catalytic hydrolysis
  • Method for preparing (S)-2-phenylbutyric acid by stereoselective enzyme catalytic hydrolysis
  • Method for preparing (S)-2-phenylbutyric acid by stereoselective enzyme catalytic hydrolysis

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Effect test

Embodiment 1

[0029] In a 25mL reaction tube, add 0.020mmol of racemic ethyl 2-phenylbutyrate as the substrate, 1mL of Tris / hydrochloric acid buffer solution (pH=6) as the reaction medium, add 10mg of different Commercial lipase was used to start the reaction, and the reaction was carried out at 600rpm and 50°C for 5h. After the reaction, the product was analyzed by high performance liquid chromatography. The results showed that: when Candida antarctica lipase A was used as a catalyst, it preferentially recognized (S)-2-phenylbutyric acid ethyl ester, and its ee p is 64.46%, c is 5.45%, and E is 4.8.

Embodiment 2

[0031] In a 25mL reaction tube, add 0.015mmol of racemic 2-phenylbutyrate as the substrate, 1mL of tris / hydrochloric acid buffer solution (pH=6) as the reaction medium, and add 30mg of Antarctic Candida Yeast lipase A, start the reaction, and react for 4 hours at 600rpm and 85°C. After the reaction, the product was analyzed by high performance liquid chromatography. The results showed that when 2-phenylbutyrate heptyl was used as the substrate, its ee p is 96.74%, c is 15.44%, and E is 71.75.

Embodiment 3

[0033] In a 25mL reaction tube, add 0.015mmol of racemic 2-phenylhexylbutyrate as the substrate, 1mL of Tris / hydrochloric acid buffer solution (pH=6) as the reaction medium, add 30mg of Antarctica Trichotrichum lipase A, start the reaction, and react for 4 hours at 600 rpm and 85°C. After the reaction, the product was analyzed by high performance liquid chromatography. The results show that: its ee p is 96.7%, c is 12.30%, and E is 68.10.

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Abstract

The invention discloses a method for kinetically separating 2-phenylbutyric acid enantiomer by using lipase. The (S)-phenylbutyric acid is prepared by high-efficiency selective lipase catalytic hydrolysis of racemic 2-phenylbutyrate. Cyclodextrin is added to a reaction system, so the substrate conversion rate is greatly improved, and the ee value is equal to or more than 96%. Compared with other separation techniques, the method has the advantages of mild reaction conditions, simplicity in operation, small environmental pollution, and obtaining of (S)-2-phenylbutyric acid with a high optical purity. The (S)-2-phenylbutyric acid is a key intermediate for synthesizing indobufen, and provides a feasible method for the preparation of the indobufen.

Description

【Technical field】 [0001] The invention belongs to the technical field of biocatalysis, and relates to a method for preparing optically pure (S)-2-phenylbutyric acid by stereoselectively catalyzing and hydrolyzing racemic 2-phenylbutyrate with lipase. 【Background technique】 [0002] Indobufen is currently the only reversible, selective multi-target exclusive antithrombotic new drug. It has quick onset, small gastrointestinal reactions, simple and convenient use, and is suitable for long-term use. It is the first choice drug for antithrombotic treatment of peripheral vascular disease, venous thrombosis disease, diabetic microcirculation disease, etc. It is also an ideal choice for preventing thrombosis during vascular surgery and hemodialysis. Studies have shown that (S)-indobufen has more significant antithrombotic activity than (R)-indobufen, and the administration of a single enantiomer can reduce the dosage of the drug, reduce the metabolic burden of the body, and reduce t...

Claims

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Application Information

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