Method for preparing D-serine and L-serine with DL-serine as raw material

A serine and raw material technology, applied in the field of preparation of D-serine and L-serine, can solve the problems of low utilization rate of raw materials, low optical purity, low optical purity of products, etc.

Inactive Publication Date: 2012-07-11
闫博
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The microbial conversion method consumes L-serine and leaves D-serine. This method has the disadvantages of low raw material utilization and poor economic efficiency. At the same time, due to incomplete microbial conversion, the optical purity of the product is not high
The enzymatic resolution method uses L-aminoacylase to hydrolyze the acetyl L-serine, and then hydrolyzes the remaining D-acetylserine with hydrochloric acid to obtain D-serine. This method has the disadvantage of low optical purity.

Method used

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  • Method for preparing D-serine and L-serine with DL-serine as raw material
  • Method for preparing D-serine and L-serine with DL-serine as raw material

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] 1) Acylation in alkaline solution to prepare N-acetyl-DL-serine;

[0017] Take 1000mol of D, L-serine and add to 0.5m 3 In a reaction kettle with purified water, stir and add 215L sodium hydroxide solution dropwise until the serine is completely dissolved, then add 105L acid anhydride dropwise to ensure that the pH value is between 9 and 11, and acylation reaction occurs below 30°C to form N-acetyl-D , L-serine, about 850L of acylation stock solution can be obtained.

[0018] 2) hydrolyzing N-acetyl D-serine in 1) with D-aminoacylase;

[0019] Dilute the acylation stock solution with purified water, and adjust the pH to 7.9-8.2, so that the volume of the split solution is 5m 3 , the concentration is about 0.2mol / L. Add 5g of D-aminoacylase, raise the temperature to 38-39°C, keep it warm for 48 hours, and when the optical rotation of the resolution solution is measured Heat the split solution to 70-80°C, add 1-2 g / L activated carbon, keep it warm for 30 minutes, and...

Embodiment 2

[0029] 1) Acylation in alkaline solution to prepare N-acetyl-DL-serine;

[0030] Take 1000mol of D, L-serine and add to 0.5m 3 In the reaction kettle of purified water, stir, and at the same time, dropwise add 215L sodium hydroxide solution until the serine is completely dissolved. Then add 105L of acid anhydride dropwise to ensure that the pH value is between 9 and 11, and acylation reaction occurs below 30°C to generate N-acetyl-D and L-serine, and about 850L of acylation stock solution can be obtained.

[0031] 2) hydrolyzing N-acetyl D-serine in 1) with D-aminoacylase;

[0032] Dilute the acylation stock solution with purified water, and adjust the pH to 7.9-8.2, so that the volume of the split solution is 5m 3, the concentration is about 0.2mol / L. Add 50g of D-aminoacylase, raise the temperature to 38-39°C, keep it warm for 60 hours, and when the optical rotation of the split solution is measured Heat the split solution to 70-80°C, add 1-2 g / L activated carbon, keep ...

Embodiment 3

[0042] 1) Acylation in alkaline solution to prepare N-acetyl-DL-serine;

[0043] Take 1000mol of D, L-serine and add to 0.5m 3 In the reaction kettle of purified water, stir, and at the same time, dropwise add 215L sodium hydroxide solution until the serine is completely dissolved. Then add 105L of acid anhydride dropwise to ensure that the pH value is between 9 and 11, and acylation reaction occurs below 30°C to generate N-acetyl-D and L-serine, and about 850L of acylation stock solution can be obtained.

[0044] 2) hydrolyzing N-acetyl D-serine in 1) with D-aminoacylase;

[0045] Dilute the acylation stock solution with purified water, and adjust the pH to 7.9-8.2, so that the volume of the split solution is 5m 3 , the concentration is about 0.2mol / L. Add 90g of D-aminoacylase, raise the temperature to 38-39°C, keep it warm for 72 hours, and when the optical rotation of the resolution solution is measured Heat the split solution to 70-80°C, add 1-2 g / L activated carbon,...

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Abstract

The invention relates to a method for preparing D-serine and L-serine with DL-serine as a raw material. The method comprises the following steps: 1) performing acylation on the DL-serine to prepare N-acetyl-DL-serine in an alkaline solution; 2) hydrolyzing the N-acetyl-D-serine in the step 1) by using D-aminoacylase; 3) extracting D-serine in the step 2) by using a strong acidic cationic resin; 4) splitting unhydrolyzed acetyl-DL-serine in the step 3) by using the L-aminoacylase; 5) separating acetyl-L-serine from the un-split acetyl-DL-serine in the step 5) by using a cationic resin column; and 6) adding the un-split acetyl-DL-serine in the step 5) into the hydrolysis solution in the step 2) for recycle. Through the combination of the steps, preparation methods of the D-serine and the L-serine can be implanted in an industrial level; the high yield and the lower waste rate of the raw material can be obtained; the steps are simplified: the utilization rate of the raw material and the product yield are increased; and the cost is reduced. Therefore, the method for preparing the D-serine and the L-serine with the DL-serine as the raw material is superior to the method in the prior art.

Description

technical field [0001] The invention relates to a method for preparing D-serine and L-serine by using DL-serine as raw material. Background technique [0002] D-serine and its derivatives are widely used in medicine and other fields. It is an important intermediate for the synthesis of new drugs such as antibacterial and antiviral drugs, food additives such as artificial sweeteners, especially D-serine as a side chain raw material for semi-synthetic antibiotics , D-serine can significantly improve the social withdrawal of autistic patients, and can be used to treat brain diseases such as schizophrenia, which has attracted the attention of academia and industry. [0003] Since serine has an active hydroxyl group, severe reaction conditions will result in the formation of a large number of by-products, so the current research or industrialization adopts a relatively mild preparation method. The reported methods for preparing D-serine mainly include microbial transformation or...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C12P41/00C12P13/06
Inventor 闫博
Owner 闫博
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