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Method for preparing D-tyrosine by enzyme method

A technology for enzymatic preparation of tyrosine, which is applied in fermentation and other directions, can solve rare problems and achieve the effects of strong anti-inhibition, reduced production costs, and strong stereoselectivity

Inactive Publication Date: 2007-01-24
安徽省恒锐新技术开发有限责任公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Therefore, so far, there are few reports on the resolution and preparation technology of D-tyrosine in foreign countries, and it is rare in China.

Method used

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  • Method for preparing D-tyrosine by enzyme method
  • Method for preparing D-tyrosine by enzyme method
  • Method for preparing D-tyrosine by enzyme method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Step 1 Preparation of N-Acetyl-DL-Tyrosine

[0025] Dissolve 36.2g of DL-tyrosine (0.2mol) and 24.0g of acetic acid (0.4mol) in 200ml of deionized water, add 24.0g of acetic anhydride (0.2mol), stir and react at 40-60°C for 3-6 hours, distill Unreacted acetic acid was recovered, cooled to room temperature and then cooled in an ice-water bath for 1 hour, then filtered, centrifuged, washed, and dried to obtain 42.6 g of product with a yield of 95.5%. The obtained N-acetyl-DL-tyrosine is used for later use.

[0026] Step 2 Purification and immobilization of D-acylated hydrolase

[0027] The commercially available D-acylase hydrolase cells are added to a dissolving tank (PH7.8), partially purified with a diethylaminoethyl chromatographic column, immobilized with an enzyme column, and stored at low temperature for future use.

[0028] After testing, each gram of wet bacteria can produce 2245 activity units of D-acylase and 852 activity units of L-acylase. The immobilized ...

Embodiment 2

[0032] Step 1 Preparation of N-Acetyl-DL-Tyrosine

[0033] Dissolve 54.3g of DL-tyrosine (0.3mol) and 36.0g of acetic acid (0.6mol) in 200ml of deionized water, add 24.0g of acetic anhydride (0.2mol), stir and react at 50-65°C for 4-6 hours, distill Recover unreacted acetic acid, cool to room temperature and then cool in an ice-water bath for 45 minutes, then filter, centrifuge, wash, and dry to obtain 64.2 g of product with a yield of 96.0%. The obtained N-acetyl-DL-tyrosine is ready for use.

[0034] Step 2D - Purification and immobilization of the acylase hydrolase

[0035] The enzyme column prepared in step 2 in Example 1 was used.

[0036] Step 3D-Acylation hydrolase splits gyro-tyrosine to prepare D-tyrosine

[0037] 64.2 g of N-acetyl-DL-tyrosine prepared in the above step 1 was dissolved in 300 ml of deionized water, and the pH value was adjusted to 7.5 with ammonia water. The reaction solution was passed through the immobilized enzyme column at 50°C, and then elut...

Embodiment 3

[0039]Step 1 Preparation of N-Acetyl-DL-Tyrosine

[0040] Dissolve 72.4g of DL-tyrosine (0.4mol) and 42.0g of acetic acid (0.7mol) in 350ml of deionized water, add 24.0g of acetic anhydride (0.2mol), stir and react at 50-60°C for 4-5 hours, distill Unreacted acetic acid was recovered, cooled to room temperature and then cooled in an ice-water bath for 1.5 hours, then filtered, centrifuged, washed, and dried to obtain 84.4 g of product with a yield of 94.6%. The obtained N-acetyl-DL-tyrosine is used for later use.

[0041] Purification and immobilization of step 2D-type aminoacyl hydrolase

[0042] The enzyme column prepared in step 2 in Example 1 was used.

[0043] Step 3D-Acylation hydrolase splits gyro-tyrosine to prepare D-tyrosine

[0044] Dissolve 84.4 g of N-acetyl-DL-tyrosine prepared in step 1 above in 500 ml of deionized water, and adjust the pH value to 7.5 with sodium hydroxide solution. The reaction solution was passed through the immobilized enzyme column at 4...

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Abstract

The present invention discloses preparation of chiral organic compound, and is especially process of preparing D-tyrosine from DL-tyrosine. The process includes the following steps: the first acylation reaction between DL-tyrosine and acylating reagent in the presence of organic acid to produce N-acetyl-DL-tyrosine; dissolving N-acetyl-DL-tyrosine in deionized water to compound 0.5-1.0 mol / L concentration solution; regulating pH value with alkali and filtering to obtain N-acetyl-DL-tyrosine solution; reaction between the N-acetyl-DL-tyrosine solution and D-acylating hydrolase fixed in enzyme column, eluting, decolorizing the reacted liquid with decolorizing agent, filtering, concentrating, cooling, crystallizing, rinsing with small amount of deionized water and drying to obtain D-tyrosine; and preparing L-tyrosine with the crystallized mother liquid. The process may be used in industrial production.

Description

technical field [0001] The invention is a method for preparing chiral organic compounds, especially a method for preparing D-tyrosine from DL-tyrosine. Background technique [0002] Tyrosine, chemical name α-amino-β-hydroxyphenylpropionic acid, also known as p-hydroxyphenylalanine. The English name is Tyrosine, which has special physiological properties and has important uses in food, feed industry and agriculture. Tyrosine is a typical neutral amino acid with a chiral carbon atom in its structure, that is, the carbon atom at the position of the amino group, so tyrosine has optical isomers, namely L-tyrosine and D-tyrosine Amino acid, the enantiomeric structure is as follows: [0003] [0004] L(-)-Tyrosine D(+)-Tyrosine [0005] L-tyrosine is a natural amino acid, its performance has long been known, and it is widely used in medicine, food, feed, chemical industry and other fields. For example, L-tyrosine can be used as an additive for food and feed, and as a raw m...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C12P13/22
Inventor 马云峰柴多里王组元
Owner 安徽省恒锐新技术开发有限责任公司
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