L-glufosinate ammonium preparation method

A glufosinate-ammonium and phosphonic acid-based technology, which is applied in chemical instruments and methods, compounds of Group 5/15 elements of the periodic table, and bulk chemical production, can solve the problems of low total yield, high price, and difficulty in separation and purification and other issues, to achieve the effect of easy industrialization, industrialization and cost reduction

Active Publication Date: 2019-02-26
SICHUAN LIER BIOTECHNOLOGY CO LTD
View PDF5 Cites 9 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0014] There are following disadvantages in this method: some intermediates are very water-soluble, difficult to separate and purify; the asymmetric reduction of double bonds needs to use expensive noble metals and ligands, which is uneconomical; the enantioselectivity of the product is low (only 84% ee), the total yield of the reaction is low (only 26.7%)
[0017] This method has the following disadvantages: the substrate is difficult to synthesize, the reaction needs multiple cofactors such as transaminase, coenzyme and amine donor, and there is no advantage in cost
[0024] This method needs to use expensive methionine as a starting material, and the reaction synthesis route is long, the total yield is relatively low, the cost is high, and there is no industrial application prospect

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • L-glufosinate ammonium preparation method
  • L-glufosinate ammonium preparation method
  • L-glufosinate ammonium preparation method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] Embodiment 1: (R=Et)

[0048] Take 760mg (4mmol) of the glufosinate-ammonium intermediate and dissolve it in 40ml of PBS buffer (0.2M, pH=8.0) solution. Add 20 mg of pyridoxal phosphate and 50 mg of nitrile hydratase (purchased from Suzhou Pilot Biotechnology Co., Ltd., product number YH1603) dissolved in 1 ml of water in turn to the reaction solution. Only one model of the product is given here for illustration. Effect of the invention), 38 mg of L-amide hydrolase dissolved in 1 ml of water (purchased from Suzhou Pilot Biotechnology Co., Ltd., product number is YH1411, only one of the models is given here to illustrate the effect of the present invention), 76 mg of ACL racemase dissolved in 1 ml of water (purchased from Suzhou Pilot Biotechnology Co., Ltd., product number is YH1507, only one model of the product is given here to illustrate the effect of the present invention). After the addition, the temperature of the system was raised to 30° C., and the reaction was...

Embodiment 2

[0049] Embodiment 2: (R=n-Bu)

[0050] Dissolve 872mg (4mmol) of glufosinate-ammonium intermediate in 40ml of PBS buffer (0.2M, pH=8.0) solution. Add 20 mg of pyridoxal phosphate and 50 mg of nitrile hydratase (purchased from Suzhou Pilot Biotechnology Co., Ltd., product number YH1603) dissolved in 1 ml of water in turn to the reaction solution. Only one model of the product is given here for illustration. Effect of the invention), 38 mg of L-amide hydrolase dissolved in 1 ml of water (purchased from Suzhou Pilot Biotechnology Co., Ltd., product number is YH1411, only one of the models is given here to illustrate the effect of the present invention), 87 mg of ACL racemase dissolved in 1 ml of water (purchased from Suzhou Pilot Biotechnology Co., Ltd., product number is YH1507, only one type of product is given here to illustrate the effect of the present invention). After the addition was completed, the temperature of the system was raised to 30° C., and the reaction was comp...

Embodiment 3

[0051] Embodiment 3: (R=H)

[0052]Take 648mg (4mmol) of the glufosinate-ammonium intermediate and dissolve it in 40ml of PBS buffer (0.2M, pH=8.0) solution. Add 20 mg of pyridoxal phosphate and 50 mg of nitrile hydratase (purchased from Suzhou Pilot Biotechnology Co., Ltd., product number YH1603) dissolved in 1 ml of water in turn to the reaction solution. Only one model of the product is given here for illustration. Effect of the invention), 38 mg of L-amide hydrolase dissolved in 1 ml of water (purchased from Suzhou Pilot Biotechnology Co., Ltd., product number is YH1411, only one of the models is given here to illustrate the effect of the present invention), 65 mg of ACL racemase dissolved in 1 ml of water (purchased from Suzhou Pilot Biotechnology Co., Ltd., product number is YH1507, only one model of the product is given here to illustrate the effect of the present invention). After the addition was completed, the temperature of the system was raised to 30° C., and the ...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

PUM

No PUM Login to view more

Abstract

The invention discloses a method for obtaining L-glufosinate ammonium with single configuration by catalytically hydrolyzing an inexpensive and easily-available glufosinate ammonium cyanamide intermediate with biological enzyme through a one-pot method, wherein the hydrolyzing process specifically comprises: 1, obtaining a glufosinate ammonium amide racemate from a racemic glufosinate ammonium cyanamide intermediate under the action of non-selective nitrile hydratase; 2, selectively hydrolyzing the L-glufosinate ammonium amide intermediate with L-amide hydrolase to obtain L-glufosinate ammonium phosphonate while racemizing the unhydrolyzed D-glufosinate ammonium amide intermediate under the action of ACL racemase to continuously convert into the L-glufosinate ammonium amide intermediate, such that the single L-glufosinate ammonium phosphonate is finally obtained through the DKR process; and 3, hydrolyzing the L-glufosinate ammonium phosphonate under the action of dilute hydrochloric acid to obtain the L-glufosinate ammonium.

Description

technical field [0001] The invention belongs to the technical fields of biopharmaceutical and biochemical industry, and in particular relates to a preparation method of L-glufosinate. Background technique [0002] Glufosinate-ammonium was successfully developed by Hearst in the 1980s. It is a phosphonic acid herbicide, an inhibitor of glutamine synthesis, and a contact-killing herbicide. It is a broad-spectrum, low-toxic, non-selective herbicide. It is also the second most herbicide-tolerant genetically modified crops in the world, and its application prospects are very broad. [0003] At present, glufosinate-ammonium sold in the market is generally a racemic mixture. If the glufosinate-ammonium product can be used with the pure optical isomer of L-configuration (structural formula ), which can reduce the consumption of glufosinate-ammonium by 50%, which is of great significance for improving atom economy, reducing use cost and alleviating environmental pressure. [0004...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

Application Information

Patent Timeline
no application Login to view more
Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/30C12P13/04
CPCC07F9/301C12P13/04Y02P20/55
Inventor 谢新开黄晓飞徐伟
Owner SICHUAN LIER BIOTECHNOLOGY CO LTD
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products