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Method for catalyzing asymmetric hydrolysis of 1,2-epoxyoctane by soybean epoxide hydrolase

A technology of epoxide and epoxide, which is applied in the field of soybean epoxide enzymatic 1, and achieves the effects of high yield, low cost of reaction medium and mild conditions

Inactive Publication Date: 2016-08-17
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although, DES has not been widely used in biocatalysis and transformation, but few studies have shown the potential of DES in biocatalysis

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] (1) Add choline chloride-urea and water in the 25mL stoppered Erlenmeyer flask to prepare 4mL of choline chloride-urea mixed solution containing 15% (v / v) (pH is 7.0); then Add 1,2-epoxyoctane to the mixed solution, wherein the final concentration of 1,2-epoxyoctane is 5mmol / L to obtain a mixed solution;

[0026] (2) Add 12 mg of soybean epoxide hydrolase to the mixed solution prepared in step (1), react for 1 h (reaction pH=7, temperature is 20° C.), and obtain a reaction mixed solution;

[0027] (3) Add 2 times the volume of ethyl acetate to the reaction mixture prepared in step (2) for extraction, get the supernatant for gas phase analysis to obtain a product yield of 40% and e.e. value 95%, further rotary evaporation, Chiral octanediol is obtained.

Embodiment 2

[0029] (1) Add choline chloride-xylitol and water in a 25mL stoppered Erlenmeyer flask to prepare 4mL containing 15% (v / v) choline chloride-xylitol mixed solution (pH is 9.0); Then add 1,2-epoxyoctane to the mixed solution, wherein the final concentration of 1,2-epoxyoctane is 10mmol / L to obtain a mixed solution;

[0030] (2) Add 12 mg of soybean epoxide hydrolase to the mixed solution prepared in step (1), and react for 24 hours (reaction pH=9 and temperature 50° C.) to obtain a reaction mixture;

[0031] (3) Add 2 times the volume of ethyl acetate to the reaction mixture prepared in step (2) for extraction, get the supernatant for gas phase analysis to obtain a product yield of 48% and e.e. value 85%, further rotary evaporation, Chiral octanediol is obtained.

Embodiment 3

[0033] (1) Add choline chloride-glycerol and water in a 25mL conical flask with a stopper to prepare 4mL of choline chloride-glycerol mixed solution (pH is 7.0) containing 15% (v / v); then Add 1,2-epoxyoctane to the mixed solution, wherein the final concentration of 1,2-epoxyoctane is 5mmol / L to obtain a mixed solution;

[0034] (2) Add 12 mg of soybean epoxide hydrolase to the mixed solution prepared in step (1), and react for 24 hours (reaction pH=7, temperature is 70°C) to obtain a reaction mixture;

[0035] (3) Add 2 times the volume of ethyl acetate to the reaction mixture prepared in step (2) for extraction, get the supernatant for gas phase analysis to obtain a product yield of 49% and e.e. value 80%, further rotary evaporation, Chiral octanediol is obtained.

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Abstract

The invention discloses a method for catalyzing asymmetric hydrolysis of 1,2-epoxyoctane by soybean epoxide hydrolase and belongs to the field of biochemical industry. With soybean epoxide hydrolase as a catalyst and a deep cosolvent as a solvent, asymmetric hydrolysis of 1,2-epoxyoctane is enzymatically catalyzed to prepare chiral octanediol. The method has the advantages of mild conditions, high synthetic yield, operation simplicity and the like and has good industrial value.

Description

technical field [0001] The invention belongs to the field of biochemical industry, and in particular relates to a method for enzymatically catalyzing the asymmetric hydrolysis of 1,2-epoxyoctane by soybean epoxide. Background technique [0002] Chiral vicinal diols are a class of valuable intermediates in organic synthesis, which can be used as raw materials to synthesize many compounds with high added value, such as chiral drugs, insecticides, optically active ferroelectric liquid crystal materials, etc. Ortho diols have very important applications in the fields of medicine, pesticides and cosmetics. In the synthesis method of vicinal diols, epoxide hydrolase catalyzed asymmetric hydrolysis of epoxides to generate vicinal diols is an economical and effective method. [0003] The solubility of epoxides in the buffer is low, and if the substrate cannot be completely dissolved, it cannot fully contact with the catalyst, which is not conducive to the progress of the reaction. ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C12P7/18
CPCC12P7/18
Inventor 娄文勇曹诗林宗敏华岳冬梅黄子轩徐红夏高辉
Owner SOUTH CHINA UNIV OF TECH
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