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Method for synthesizing esbiothrin pesticide intermediate through enzyme technology

An enzymatic synthesis and pesticide technology, applied in the direction of fermentation, can solve the problems of difficult application, low product purity, low target protein content, etc., and achieve the effects of simple product separation, high product purity, and high reaction conversion rate.

Active Publication Date: 2016-05-11
CODEXIS INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

WO8706269 discloses a method for using microorganisms to resolve permethrin methyl ester. The method utilizes microorganism cells to resolve substrates. The amount of cells used is 50% of the substrate concentration, the reaction time is 96 hours, and the product purity <93%, difficult to apply
The problem faced by the above methods is that the amount of target protein contained in the wild-type microbial catalyst is low, and it contains other proteins, and the hydrolytic enzymes in it may interfere with the reaction, so the purity of the product is low
[0005] In summary, there is currently no effective method to obtain 1 by enzymatic resolution

Method used

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  • Method for synthesizing esbiothrin pesticide intermediate through enzyme technology
  • Method for synthesizing esbiothrin pesticide intermediate through enzyme technology
  • Method for synthesizing esbiothrin pesticide intermediate through enzyme technology

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Take 1 g of mixed methyl esters of cis and trans DV methyl chrysanthemum acid isomers with a mass ratio of 4:6 (the theoretical yield of product 1 is 30%, the same below), add pH7.0, 0.1M phosphoric acid Salt buffer solution 19mL, acetonitrile 1mL, lipase LipasePS (purchased from AMANO / Amano Enzyme Company) 1g, after 2 hours of reaction at 30 ℃, an equal volume of ethyl acetate was extracted, detected by gas chromatography, the conversion rate was 4.5%, the four products The ratio (1:2:3:4) is 2:94.5:0:3.5.

Embodiment 2

[0029] Take 1 g of mixed methyl esters of cis and trans DV methyl chrysanthemum acid isomers, add pH 7.0, 19 mL of 0.1 M phosphate buffer solution, 1 mL of acetonitrile, 1 g of Aspergillus saitoi protease (purchased from sigma company), and react at 30 ° C After 2 hours, an equal volume of ethyl acetate was extracted and detected by gas chromatography. The conversion rate was 5.3%, and the ratio (1:2:3:4) of the four products was 94.4:0.7:0:4.9.

Embodiment 3

[0031] Take 1 g of mixed methyl esters of cis and trans DV methyl chrysanthemum isomers, add pH 7.0, 19 mL of 0.1 M phosphate buffer solution, 1 mL of acetonitrile, and esterase CES-E2 (purchased from AMANO / Amano Enzyme Co., Ltd. The same below) 1g, reacted at 30°C for 2 hours, extracted with equal volume of ethyl acetate, detected by gas chromatography, the conversion rate was 24.8%, and the ratio of the four products (1:2:3:4) was 93.1:4:0: 2.9.

[0032] Can find out from embodiment 1,2,3, select the Aspergillussaitoi protease produced by sigma company or the esterase CES-E2 produced by AMANO / Amano Enzyme Company as the hydrolase, the yield of its product 1 will be obviously higher than that selected from Yield obtained by the lipase LipasePS of AMANO / Amano Enzyme Co., Ltd. as a hydrolase.

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Abstract

The invention discloses a method for synthesizing an esbiothrin pesticide intermediate through an enzyme technology. The method is characterized in that cis- and trans-chrysanthemic acid isomer mixed DV methyl chrysanthemate with the structure of a compound 5 is adopted as a substrate, the feeding concentration of the substrate is 1-50g / L, and a polyester pesticide intermediate is generated through a hydrolysis reaction in a buffering solution with the temperature of 25-50DEG C and the pH value of 6.0-8.0 under the action of hydrolase, wherein the feeding mass ratio of cis-isomer to trans-isomer in the mixed DV methyl chrysanthemate is 2:8-6:4, the hydrolase is protease or esterase, and the feeding mass of the hydrolase is 10-100% of the mass of the substrate. The method for preparing the polyester pesticide intermediate has the advantages of simple process, short reaction time, high conversion rate, high product purity, environmental protection, and suitableness for industrial production.

Description

technical field [0001] The invention relates to the field of biochemical technology, in particular to a method for enzymatically synthesizing a polyester insecticide intermediate. Background technique [0002] (1R,3R)-2,2-Dimethyl-3-(2,2-dichlorovinyl)cyclopropanecarboxylic acid (Formula 1), also known as permethrin, DV chrysanthemic acid, is the The derivative whose methyl group is substituted by chlorine atom is used to produce the intermediate of pyrethroid pesticide, which has higher activity and lower consumption than pyrethroid pesticide (methyl group is not substituted by chlorine). According to the latest report released by MarketsandMarkets, the pyrethroid insecticides market was valued at approximately USD 2,559.62 million in 2014 and is expected to grow at a CAGR of 4.8% to USD 3,233.24 million by 2019. [0003] [0004] The methods for preparing 1 include chemical and biological methods, the key point of which is to obtain high-purity 1 from the other three i...

Claims

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Application Information

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IPC IPC(8): C12P7/40
CPCC12P7/40
Inventor 陶军华乐庸堂薛锐吴菊
Owner CODEXIS INC
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