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Enzyme-chemocatalysis racemization removing preparation method for L-glufosinate-ammonium

A technology of chemical catalysis and glufosinate-ammonium is applied in the field of enzymatic preparation of chiral pesticides to achieve the effect of reducing process cost, low cost and simple process

Inactive Publication Date: 2016-05-11
重庆惠健生物科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The theoretical yield of biological resolution method is only 50%

Method used

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  • Enzyme-chemocatalysis racemization removing preparation method for L-glufosinate-ammonium

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Add 20gDL-glufosinate-ammonium to 200mL ammonium formate (1mol / L, pH6.5) solution, stir to dissolve, add 2g immobilized D-amino acid oxidase (50u / g), 0.2mL catalase (50000u / mL) and 2g of palladium carbon (10%), continuously fed with oxygen, stirred and reacted at 30°C for 24h, and the D-enantiomer was completely reacted by chiral HPLC. The reaction solution was filtered, and the filtrate was adjusted to pH 8.0 with 28% ammonia water, concentrated under reduced pressure at 80°C to about 40 mL, cooled in an ice bath, and solids were precipitated, and dried to obtain 18 g L-glufosinate-ammonium with a yield of 90%, a purity of 98.4%, and ee99 .3%.

Embodiment 2

[0021] Add 20gDL-glufosinate-ammonium to 200mL1mol / L ammonium formate (pH6.5), stir to dissolve, add 4g immobilized D-amino acid oxidase (50u / g), 0.4mL catalase (50000u / mL) and 4g palladium carbon (10%), continuously fed with oxygen, stirred at 30°C for 12 hours, and the D-enantiomer was completely reacted by chiral HPLC. The reaction solution was filtered, and the filtrate was adjusted to pH 8.0 with 28% ammonia water, concentrated under reduced pressure at 80°C to about 40 mL, cooled in an ice bath, and solids were precipitated, and dried to obtain 19.6 g L-glufosinate-ammonium with a yield of 98% and a purity of 99.5%. ee99.8%.

Embodiment 3

[0023] Add 40gDL-glufosinate-ammonium to 200mL1mol / L ammonium formate (pH6.5), stir to dissolve, add 4g immobilized D-amino acid oxidase (50u / g), 0.4mL catalase (50000u / mL) and 4g palladium carbon (10%), continuously fed with oxygen, stirred at 30°C for 24 hours, and the D-enantiomer was completely reacted by chiral HPLC. The reaction solution was filtered, and the filtrate was adjusted to pH 8.0 with 28% ammonia water, concentrated under reduced pressure at 80°C to about 40 mL, cooled in an ice bath, and solids were precipitated, and dried to obtain 34 g L-glufosinate-ammonium with a yield of 85%, a purity of 96.3%, and ee98 .6%.

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Abstract

The invention discloses an enzyme-chemocatalysis racemization removing preparation method for L-glufosinate-ammonium. According to the method, a one-pot reaction manner is adopted, under the molecular oxygen, immobilization D-amino acid oxidase catalyzes D-enantiomer in an enantioselectivity mode into 2-imino-4-(hydroxy methyl phosphonyl) butyric acid in a dehydrogenation mode, and palladium-ammonium formate catalyzes 2-imino -4-(hydroxy methyl phosphonyl) butyric acid into DL-glufosinate-ammonium in an in-situ reduction mode. Hydrogen peroxide produced in the process is efficiently decomposed into water and oxygen through catalase. Complete reacemization removing of DL-glufosinate-ammonium and efficient preparing of L-glufosinate-ammonium are achieved through biological oxidation-chemical reduction circulation. The method has the advantages that the process is simple, cost is low, environmental friendliness is achieved, and energy is saved. High-concentration DL-glufosinate-ammonium can be converted into L-glufosinate-ammonium. The yield is 90%, the optical purity of the product is 99%, and the method is suitable for industrial production of L-glufosinate-ammonium.

Description

technical field [0001] The invention relates to an enzyme-chemically catalyzed deracemization preparation method of L-glufosinate-ammonium, and belongs to the technical field of enzymatic preparation of chiral pesticides. Background technique [0002] Glufosinate (Glufosinate) developed by Hoechst in Germany is a glutamine synthetase (GS) inhibitor, which can inhibit all known forms of GS, leading to nitrogen metabolism disorder and excessive accumulation of ammonia in plants. , Chloroplast disintegration, thereby inhibiting photosynthesis, eventually leading to plant death. Glufosinate-ammonium has strong herbicidal activity and can effectively control almost all kinds of weeds tested. It is safe to crops, has high activity, wide herbicidal spectrum, and small phytotoxicity. It is an ideal herbicide for transgenic resistant crops at present. Glufosinate-ammonium is also an excellent fungicide. [0003] Glufosinate-ammonium contains a chiral center, the herbicidal activity...

Claims

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Application Information

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IPC IPC(8): C12P41/00C12P13/00
CPCC12P13/00C12P41/00
Inventor 夏仕文方国兰熊文娟韦燕婵
Owner 重庆惠健生物科技有限公司
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