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Method for producing D-phenylalanine by using L-phenylalanine as raw material

A technology for phenylalanine and raw materials, which is applied in the field of D-enzyme splitting and preparing D-phenylalanine, can solve the problems of high cost, long process flow, low optical purity and the like, and achieves low cost, simple process flow and high product quality. high purity effect

Inactive Publication Date: 2012-08-01
闫博
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] At present, the domestic D-phenylalanine production technology roughly has the following types: 1. Fermentation-aminoacylase split method. process, and then produced by hydrolysis with aminoacylase, the product produced by this method has low optical purity and high cost
2. Produce DL-phenylalanine by chemical synthesis process, and then carry out chemical resolution. This method does not require racemization, but there is no mature synthesis method for DL-phenylalanine at present
3. Hydantoinase directly enzymatically synthesizes D-phenylalanine. This method is currently only in the experimental stage because of its low enzyme activity.
4. The chemical synthesis of D-phenylalanine is produced by a chemical resolution process. This method has a long process and high cost

Method used

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  • Method for producing D-phenylalanine by using L-phenylalanine as raw material

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Acylation of L-phenylalanine

[0023] Weigh 300kgL-phenylalanine and dissolve it in 800L pure water, adjust the pH to 8-9 with 30% NaOH solution, about 200L of 30% NaOH is required. After the dissolution is complete, control the solution temperature at 30-35°C, and add acetic anhydride dropwise until the solution reacts with ninhydrin without color change, and the reaction is complete.

[0024] Acetyl-L-phenylalanine racemization

[0025] Use 30% hydrochloric acid to adjust the pH to 4-5 with about 0.8m3 acetylated-L-phenylalanine acylation solution with a concentration of about 0.04kg / L obtained in the previous step, add acetic anhydride dropwise at 60°C for racemization, Detection of racemate After the reaction, add 30% hydrochloric acid to adjust the pH to 1-2, cool and crystallize, filter out the crystals and dry them to obtain 30 kg of acetyl-DL-phenylalanine.

[0026] Resolution and separation of D-phenylalanine

[0027] Weigh 200kg of acetyl-DL-phenylalanine...

Embodiment 2

[0029] Acylation of L-phenylalanine

[0030] Weigh 330kgL-phenylalanine and dissolve it in 800L pure water, adjust the pH to 10-11 with 30% NaOH solution, about 200L of 30% NaOH is required. After the dissolution is complete, control the solution temperature at 35-40°C, and add acetic anhydride dropwise until the solution reacts with ninhydrin without color change, and the reaction is complete.

[0031] Acetyl-L-phenylalanine racemization

[0032] Use 30% hydrochloric acid to adjust the pH to 5-6 with about 0.8m3 acetylated-L-phenylalanine concentration of 0.04kg / L obtained in the previous step, add acetic anhydride dropwise at 70°C for racemization, and detect racemic solution After the reaction, add 30% hydrochloric acid to adjust the pH to 1-2, cool and crystallize, filter out the crystals and dry them to obtain 30 kg of acetyl-DL-phenylalanine.

[0033] Resolution and separation of D-phenylalanine

[0034] Weigh 200kg of acetyl-DL-phenylalanine to prepare a solution w...

Embodiment 3

[0036] Acylation of L-phenylalanine

[0037] Weigh 400kgL-phenylalanine and dissolve it in 800L pure water, and adjust the pH to 12-13 with 30% NaOH solution, and about 200L of 30% NaOH is required. After the dissolution is complete, control the solution temperature at 35-40°C, and add acetic anhydride dropwise until the solution reacts with ninhydrin without color change, and the reaction is complete.

[0038] Acetyl-L-phenylalanine racemization

[0039] Use 30% hydrochloric acid to adjust the pH to 5-6 with about 0.8m3 acetylated-L-phenylalanine concentration of 0.04kg / L obtained in the previous step, add acetic anhydride dropwise at 90°C for racemization, and detect racemic solution After the reaction, add 30% hydrochloric acid to adjust the pH to 3-4, cool and crystallize, filter out the crystals and dry them to obtain 30 kg of acetyl-DL-phenylalanine.

[0040] Resolution and separation of D-phenylalanine

[0041] Weigh 200kg of acetyl-DL-phenylalanine to prepare a so...

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Abstract

The invention relates to a method for producing D-phenylalanine by using L-phenylalanine as a raw material. The method comprises the following steps: preparing the L-phenylalanine into 0.3-0.4kg / L aqueous solution; adjusting the pH value to 8-13 with sodium hydroxide solution; dropping acetic anhydride for acylating; controlling the reaction temperature below 40DEG C until no color displays in a ninhydrin reaction; adjusting the pH value of the acylated acetyl-L-phenylalanine to 4-6 by using hydrochloric acid; when the temperature is raised to 60-90DEG C, dropping the anhydride for racemizing; when a rotation value of a racemic liquid is less than or equal to 0.1, adjusting the pH value of the racemic liquid to 1-4 with the hydrochloric acid and cooling and crystallizing to obtain an acetyl-DL-phenylalanine crystal; preparing the obtained acetyl-DL-phenylalanine crystal into 0.04kg / L resolution liquid, adjusting the pH value to 7.8-8.2, adding 15mg / L enzyme D, preserving the heat of 40DEG C for 24 hours and stopping resolution; and extracting the resolution liquid through cation exchange resin to obtain the D-phenylalanine. The method disclosed by the invention has the advantages of simple process flow, capability of obtain high-purity products and low cost.

Description

technical field [0001] The invention relates to the technical field of preparing D-phenylalanine, in particular to a technology for preparing D-phenylalanine by splitting and preparing D-phenylalanine using L-phenylalanine as a raw material. technical background [0002] D-phenylalanine is an important chiral amino acid with a wide range of uses. Especially in recent years, the use of D-phenylalanine in food and medicine has been fully developed, for example: for the production of heterocyclic dipeptide derivatives that promote hormone release, the production of thrombin inhibitors, endopeptidase inhibitors, the production of HIV inhibitors antineoplastic drugs and diabetes treatment drugs. In addition, D-phenylalanine can also be used as anti-inflammatory analgesic, anti-stress agent, chiral intermediate, etc. Therefore, D-phenylalanine is in great demand worldwide. [0003] At present, the domestic D-phenylalanine production technology roughly has the following types: 1...

Claims

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Application Information

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IPC IPC(8): C12P41/00C12P13/22
Inventor 闫博
Owner 闫博
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