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Method for preparing droxidopa

A technology of coenzyme and enzyme reaction, applied in the field of preparation of droxidopa, can solve the problems of large amount of glycine, poor stereoselectivity, and lack of conditions for industrialization, etc., and achieve the effect of simple operation, mild conditions, and cost reduction

Active Publication Date: 2019-05-28
湖南引航生物科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this method still has defects such as low conversion rate, large amount of glycine, poor stereoselectivity, and difficult separation and purification of products, and does not yet have the conditions for industrialization

Method used

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  • Method for preparing droxidopa
  • Method for preparing droxidopa
  • Method for preparing droxidopa

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Add 10g 3,4-dihydroxybenzaldehyde, 100mg sodium bisulfite, 10g L-threonine, 40mg pyridoxal phosphate, 300mL 100mM phosphate buffer (pH7.5 ) heated to 30° C. and stirred evenly by magnetic force, adding 1 g of transaldolase enzyme powder (purchased from Suzhou Pivot Biotechnology Co., Ltd., product number is YH1065, only one of the models is given here to illustrate the effect of the present invention), Stirring reaction was started, and after 20 hours, a sample was taken by HPLC to detect that the conversion rate was above 80%. After the reaction is finished, adjust the pH of the system to 1 with hydrochloric acid, heat up to 80°C for 2 hours, filter, and remove the protein. The filtrate was concentrated to dryness, and the residue was dissolved in isopropanol. The insoluble matter was removed by filtration, the pH was adjusted to about 6 with triethylamine, and a solid was precipitated to obtain 8.2 g of the product, ee=94%, dr=96:4.

Embodiment 2

[0035] Add 100g of 100mM phosphate buffer (pH=7.5) to a 250mL reaction flask under argon atmosphere, add 100mg of sodium bisulfite, 10g of 3,4-dihydroxybenzaldehyde, 10g of L-threonine and glucose under stirring 12 g, the system was stirred for 10 minutes. Use 3M sodium hydroxide to adjust the pH of the system to 7.5, control the temperature of the system to 35°C and stir evenly, then add 20 mg of pyridoxal phosphate, 20 mg of nicotinamide adenine dinucleotide, and 0.5 g of transaldolase enzyme powder (purchased from Suzhou Yinhang Biotechnology Co., Ltd., product number is YH1065), 0.5g acetaldehyde reductase enzyme powder (purchased from Suzhou Pivot Biotechnology Co., Ltd., product number is YH2012) and 0.5g glucose dehydrogenase enzyme powder (purchased from Suzhou Pivot Biotechnology Co., Ltd. (the product number is YH1901), started the stirring reaction, and kept the pH of the system at 7.5 with 3M NaOH during the reaction. After 20 hours, a sample was taken for HPLC det...

Embodiment 3

[0037] Add 100g of 100mM phosphate buffer (pH=7.5) to a 250mL reaction flask under argon atmosphere, add 100mg of sodium bisulfite, 10g of 3,4-dihydroxybenzaldehyde, 10g of L-threonine and 10g of isopropanol, and the system was stirred for 10 minutes. Use 3M sodium hydroxide to adjust the pH of the system to 7.5, control the temperature of the system to 35°C and stir evenly, then add 20 mg of pyridoxal phosphate, 20 mg of nicotinamide adenine dinucleotide, and 0.5 g of transaldolase enzyme powder (purchased from Suzhou Yinhang Biotechnology Co., Ltd., product number is YH1065), 0.5g acetaldehyde reductase enzyme powder (purchased from Suzhou Pivot Biotechnology Co., Ltd., product number is YH2012) and 0.5g alcohol dehydrogenase enzyme powder (purchased from Suzhou Pivot Biotechnology Co., Ltd., product number is YH2023), start stirring reaction, after 20 hours sampling HPLC detection, the conversion rate is more than 99%. After the reaction is finished, adjust the pH of the s...

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Abstract

The invention discloses a method for preparing droxidopa. The method is characterized in that 3,3-dihydroxy benzaldehyde and L-threonine are used as raw materials to synthesize the droxidopa under theexistence of transaldolase.

Description

technical field [0001] The invention relates to a method for preparing drsidopa, belonging to the technical fields of biopharmaceuticals and biochemical industries. Background technique [0002] Drsidopa is a new anti-Parkinson drug. It can treat various symptoms caused by norepinephrine deficiency, such as stiff gait in Parkinson's patients, dizziness and fatigue caused by orthostatic hypotension. It is widely used in the field of biomedicine, so exploring a mild, efficient and economical method to prepare drsidopa has attracted the attention of chemical and biological workers. [0003] The structural formula of drsidopa is as follows: [0004] [0005] At present, there are mainly the following methods for preparing droxidopa: using 3,4-dihydroxybenzaldehyde as the starting material, and preparing it through multi-step chemical reactions (patent US3920728; EP0024210A1; Chinese Journal of Synthetic Chemistry, 2010, 18, 124-127, etc.) , the flow is as follows: [0006...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C12P13/04
Inventor 谢新开黄晓飞徐伟
Owner 湖南引航生物科技有限公司
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