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A biological enzyme-catalyzed flow process for preparing 2-amino-3-substituted phenyl-3-hydroxypropionic acid

A kind of technology of hydroxypropionic acid and hydroxypropionic acid, applied in the field of compound preparation

Active Publication Date: 2022-07-12
杭州濡湜生物科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there is no report on the industrial biosynthesis method of 2-amino-3-substituted phenyl-3-hydroxypropionic acid. The present invention adopts bio-enzyme catalysis technology combined with flow reaction process to design a new process of environmental protection, high efficiency and energy saving. It fills the blank of industrial biosynthesis of this kind of products

Method used

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  • A biological enzyme-catalyzed flow process for preparing 2-amino-3-substituted phenyl-3-hydroxypropionic acid
  • A biological enzyme-catalyzed flow process for preparing 2-amino-3-substituted phenyl-3-hydroxypropionic acid
  • A biological enzyme-catalyzed flow process for preparing 2-amino-3-substituted phenyl-3-hydroxypropionic acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Example 1 Synthesis of 2-amino-3-p-methylsulfonylphenyl-3-hydroxypropionic acid

[0035] Add 300L of activated macroporous adsorption resin D301 (resin density about 0.7g / ml), stirred at 5~10℃ for 13h, then filtered the macroporous adsorption resin and washed with 500L purified water to obtain immobilized aldolase resin. The phosphate buffer solution obtained after filtration is repeatedly used for immobilization as the solvent of the enzyme solution, and the purified water after washing is repeatedly used to wash the macroporous adsorption resin after filtration.

[0036] Dissolve 7.8Kg of glycine in 1000L of purified water, heat it to 40°C (preheat to the reaction temperature catalyzed by the enzyme in advance, and save the time in the early stage of the reaction), under stirring conditions, add 18.5Kg of p-methylsulfonylbenzaldehyde and 13g of ZnCl in turn. 2 , adjust the pH to 7.5. 10 L of the immobilized aldolase resin prepared above was filled in the enzyme-cata...

Embodiment 2

[0037] Example 2 Fixed bed separation of 2-amino-3-p-methylsulfonylphenyl-3-hydroxypropionic acid and glycine

[0038] Take 100L of the reaction mixture solution obtained in Example 1, fill 100L of HZ930 resin in the separation fixed bed, the reaction mixture solution flows through the separation fixed bed at a flow rate of 10BV / h, and after the reaction mixture solution all enters the separation fixed bed, at 10BV / h The flow rate of 400L of purified water was added immediately, and the first 150L of effluent was collected. The effluent was detected as a dilute solution of glycine, which could be recovered and applied to Example 1 after vacuum concentration at 80°C. After collection, 350L of effluent was detected as a dilute solution of 2-amino-3-p-methylsulfonyl phenyl-3-hydroxypropionic acid, concentrated in vacuo at 80°C to a mass concentration of 20%, 2-amino-3- The yield of p-methylsulfonylphenyl-3-hydroxypropionic acid was 96.7%. Wherein the purified water produced in t...

Embodiment 3

[0039] Example 3 Preparation of 2-amino-3-p-methylsulfonylphenyl-3-hydroxypropionic acid finished product

[0040] Take 1Kg of 2-amino-3-p-methylsulfonylphenyl-3-hydroxypropionic acid concentrate (20% mass concentration) into a 2L round-bottomed flask, control the temperature to -5°C, stir slowly for 20h, there are a lot of white The crystals were precipitated, filtered, and dried under vacuum at 80° C. to collect 136.4 g of the product 2-amino-3-p-methylsulfonylphenyl-3-hydroxypropionic acid, the yield was 68.2%, and the HPLC purity was 98%. The product obtained in Example 3 1 H-NMR spectrum such as image 3 shown. The remaining product is in the filtrate, which can be recycled, that is, combined with the next batch of concentrated liquid for crystallization.

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Abstract

The invention discloses a biological enzyme catalytic flow process for preparing 2-amino-3-substituted phenyl-3-hydroxypropionic acid. The immobilized aldolase is used as a biological catalyst, and substituted benzaldehyde and glycine are used as substrates. Metal ion is the enzymatic agent, water is the solvent, PH is 6~9, temperature is 35~65℃, the enzymatic reaction is designed as a very fast flow reaction, and the whole reaction solution is enzymatically catalyzed by catalytic fixed bed at 100~800BV / h. The excess raw materials and products are separated by a separation fixed bed containing a specific complex resin, and the divalent metal ion enzymatic agent is completely removed. The glycine dilute solution is concentrated and recovered for use. 2-amino-3-substituted phenyl-3-hydroxyl The propionic acid is concentrated, crystallized and dried to obtain the product, and the water obtained by concentration is recovered and applied mechanically. The enzyme-catalyzed conversion rate of the invention is over 96%, and the product separation efficiency is over 94%, forming a set of green and environment-friendly production processes with self-circulation of solvent materials and no discharge of three wastes.

Description

technical field [0001] The invention relates to the technical field of compound preparation, in particular to a biological enzyme-catalyzed flow process for preparing 2-amino-3-substituted phenyl-3-hydroxypropionic acid. Background technique [0002] 2-Amino-3-substituted phenyl-3-hydroxypropionic acid is an important class of pharmaceutical intermediates and chemical intermediates, especially 2-amino-3-(4-methylsulfonylphenyl)-3-hydroxypropionic acid. Acid and 2-amino-3-(4-chlorophenyl)-3-hydroxypropionic acid, widely used in the preparation of human antibiotics, poultry and livestock antibiotics, etc., its representative drugs such as chloramphenicol, thiamphenicol, fluorobenzene Niko and more. [0003] The current mainstream of 2-amino-3-substituted phenyl-3-hydroxypropionic acid synthesis is chemical synthesis. Although the chemical synthesis method is simple to operate, a large amount of water, heavy metals and highly toxic hydrogen sulfide are used in the reaction pr...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C12N11/082C12P13/00
CPCC12N11/082C12N9/88C12P13/001Y02P20/10
Inventor 王喆明谭昊
Owner 杭州濡湜生物科技有限公司
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