Method for preparing chloramphenicol

A technology of chloramphenicol and coenzyme, which is applied in the field of preparation of chloramphenicol, can solve the problems of high environmental hazards, cumbersome disassembly steps, and increased reaction steps, and achieve the effects of cost reduction, mild conditions, and simple operation

Active Publication Date: 2020-09-15
湖南引航生物科技有限公司
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  • Summary
  • Abstract
  • Description
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  • Application Information

AI Technical Summary

Problems solved by technology

[0008] 1. This route requires chiral resolution, and the theoretical yield of the resolution is only 50%, which leads to the yield of the whole route being below 30%. In addition, the steps of resolution are very cumbersome, which brings a great deal of burden to industrial production. the inconvenience
[0009] 2. In this route, acetyl group protection and deprotection are required, the atom economy is poor and the increase of reaction steps reduces the overall yield, and also increases the difficulty of industrial production
[0010] 3. Aluminum isopropoxide is used in the reduction step of this route. This process produces a large amount of three wastes that are difficult to handle, which is very harmful to the environment.

Method used

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  • Method for preparing chloramphenicol
  • Method for preparing chloramphenicol
  • Method for preparing chloramphenicol

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Embodiment 1: transaldolase catalyzed preparation of amino acid

[0030] Add 10g of p-nitrobenzaldehyde, 10g of L-threonine, 40mg of pyridoxal phosphate, 300mL of 100mM phosphate buffer (pH7.5) into a 500mL reaction bottle and heat to 30°C with magnetic stirring, then add 1g of transaldolase Enzyme powder (purchased from Suzhou Pilot Biotechnology Co., Ltd., product number is YH1062, here only provides one of the models of products to illustrate the effect of the present invention), start stirring reaction, after 20 hours, sampling HPLC detects that the conversion rate is 90% above. After the reaction was completed, the white solid was collected by filtration, and the white solid product was recrystallized with ethanol to obtain 9.4 g of the product, ee>99%, dr>99:1. .

Embodiment 2

[0032] Add 100 g of 100 mM phosphate buffer solution (pH=7.5) into a 250 mL reaction flask, add 10 g of p-nitrobenzaldehyde, 10 g of L-threonine and 12 g of glucose under stirring, and stir the system 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 YH1062), 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 detection, and the conversion rate was above...

Embodiment 3

[0034] Add 100 g of 100 mM phosphate buffer (pH=7.5) into a 250 mL reaction flask, add 10 g of p-nitrobenzaldehyde, 10 g of L-threonine and 10 g of isopropanol under stirring, and stir the system 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 YH1062), 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 was completed, the white solid was collected by filtration, and the white so...

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Abstract

The invention provides a method for preparing chloramphenicol. (2S,3R)-p-nitrophenyl serine is prepared from p-nitrobenzaldehyde and L-threonine which are low in price and are easy to obtain under action of transaldolase, and a target product chloramphenicol is obtained through reduction and dichloroacetylation of the amino acid intermediate.

Description

technical field [0001] The invention relates to a method for preparing chloramphenicol, which belongs to the technical fields of biopharmaceuticals and biochemical industries. Background technique [0002] Chloramphenicol is one of the broadest-spectrum antibiotics currently on the market. Its antibacterial mechanism is to bind to the 50S subunit of the ribosome and inhibit peptidyltransferase, thereby inhibiting protein synthesis. It can effectively control most Gram-negative and positive bacteria, influenza bacilli, pertussis bacilli, Shigella, Escherichia coli, Klebsiella pneumoniae, Proteus, Pseudomonas aeruginosa, Rickettsia, Chlamydia trachomatis, etc. It is widely used in the field of biomedicine, so exploring a mild, efficient and economical method to prepare chloramphenicol has attracted the attention of chemical and biological workers. [0003] Chloramphenicol, its structural formula is as follows: [0004] [0005] The current method for industrial preparatio...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C12P13/02
CPCC12P13/02
Inventor 谢新开黄晓飞杜好勉
Owner 湖南引航生物科技有限公司
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