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Method for synthetizing chiral cyclic alkyl amino acid by amino transferase

A technology of aminotransferase and alkyl amino acid, which is applied in the field of synthesizing chiral cyclic alkyl amino acid by using aminotransferase, can solve the problems of high production cost, high price and low yield, and achieve mild reaction conditions and stable process , Environmentally friendly effect

Active Publication Date: 2013-07-10
ASYMCHEM LAB TIANJIN +5
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] Various split methods have the disadvantages of being difficult to carry out industrialized production, relatively high cost and low yield. The theoretical yield can reach 50%, but the yield in actual application is only 10%-20%. Therefore, the application Such methods are very expensive to produce
Sometimes the chemical resolution method also uses expensive chiral resolving agents, which greatly increases the production cost; in addition, the chemical reagents used are more complicated to operate, and the post-processing does not take advantage of environmental protection.

Method used

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  • Method for synthetizing chiral cyclic alkyl amino acid by amino transferase
  • Method for synthetizing chiral cyclic alkyl amino acid by amino transferase
  • Method for synthetizing chiral cyclic alkyl amino acid by amino transferase

Examples

Experimental program
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Effect test

Embodiment 1

[0027] Embodiment 1: the method for utilizing aminotransferase to synthesize chiral cyclic alkyl amino acids is characterized in that the specific steps are as follows:

[0028] (1) Feeding: Add 2.12kg of the main raw material 2-cyclohexyl-2-oxoacetic acid sodium salt to a 200L reactor, add 100L of phosphate buffer (50mM, pH=7.0), and make the main raw material 2-cyclohexyl- 2-Oxyacetic acid sodium salt is uniformly dissolved in phosphate buffer;

[0029] (2) Add amino donor: Add 1.75kg of L-glutamic acid as amino donor to the 200L reactor, stir until completely dissolved, and adjust the system to pH=7.0;

[0030] (3) Add aminotransferase and coenzyme: Add 0.03kg coenzyme pyridoxal phosphate PLP and 0.21kg aminotransferase main enzyme BcATes to the 200L reactor;

[0031] (4) Reaction: The system was stirred in a reaction kettle at a stirring speed of 150 rpm, and kept at 30°C for 72 hours; the filtrate was concentrated, filtered with suction, and rinsed to obtain a solid crud...

Embodiment 2

[0033] Embodiment 2: the method for utilizing aminotransferase to synthesize chiral cyclic alkyl amino acid is characterized in that the specific steps are as follows:

[0034] (1) Feeding: Add 1.25kg of main raw material sodium cyclopentylpyruvate to a 200L reactor, and add 100L of phosphate buffer (100mM, pH=8.0), so that the main raw material sodium cyclopentylpyruvate is evenly dissolved in phosphoric acid in salt buffer;

[0035] (2) Add amino donor: Add 11.21kg of L-glutamic acid as amino donor to the 200L reactor, stir until completely dissolved, and adjust the system to pH=8.0;

[0036] (3) Add aminotransferase and coenzyme: Add 0.025kg coenzyme pyridoxal phosphate PLP and 0.12kg aminotransferase main enzyme BcATen to the 200L reactor;

[0037] (4) Reaction: The system was stirred in the reaction kettle at a stirring speed of 200rpm, and kept at 25°C for 60h;

[0038] (5) Post-treatment: system sampling tracking, raw material conversion is completed, add concentrated...

Embodiment 3

[0040] Embodiment 3: the method for utilizing aminotransferase to synthesize chiral cyclic alkyl amino acid is characterized in that the specific steps are as follows:

[0041] (1) Feeding: Add 1kg of main raw material cycloheptylpyruvate to the 200L reactor Add 100L phosphate buffer (50mM, pH=7.5) to make the main raw material cycloheptylpyruvate Uniformly disperse in phosphate buffer, then add 0.71kg NaOH to make sodium salt, and evenly dissolve in phosphate buffer;

[0042] (2) Add amino donor: Add 1.56kg of L-aspartic acid as amino donor to the 200L reactor, stir until completely dissolved, and adjust the system to pH=7.5;

[0043] (3) Add aminotransferase and coenzyme: Add 0.1kg of coenzyme pyridoxal phosphate PLP and 0.5kg of aminotransferase main enzyme AAT into the 200L reactor;

[0044] (4) Reaction: The system was stirred in the reaction kettle at a stirring speed of 250rpm, and kept at 30°C for 48h;

[0045] (5) Post-treatment: system sampling and tracking, aft...

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Abstract

The invention discloses a method for synthetizing chiral cyclic alkyl amino acid by amino transferase. The commercialized material ketonic acid or corresponding soluble ketonic acid salt compound in the market is selected as an initial material; the initial material is dissolved into phosphate buffer, and added to an amino supply body; pyridoxal phosphate (PLP) and amino transferase main enzyme are added to a system containing the amino supply body and main material ketonic acid or corresponding soluble ketonic acid salt compound to react under constant temperature, and obtaining a product with a high ee value, wherein n is equal to 1, 2, 3, 4, 5, or obtaining a product wherein n is equal to 0 and 1. The method is stable in technological condition, simple to operate, high in yield, low in cost, and suitable for large-scale production, and beneficial for environmental protection; and a novel train of thought and a method are provided for the preparation of chiral cyclic alkyl amino acid compound.

Description

(1) Technical field: [0001] The invention relates to a method for synthesizing chiral cyclic alkyl amino acid, in particular to a method for synthesizing chiral cyclic alkyl amino acid by using aminotransferase. (2) Background technology: [0002] Due to its high economic benefits and the specificity of enzymes, asymmetric biocatalysis has the advantages of high stereoselectivity, chemical and optical specificity. Important method for intermediates. Among them, the method for preparing chiral amino acids is mainly based on the resolution of racemic mixtures by liquid chromatography and the resolution by chemical resolution. [0003] Various split methods have the disadvantages of being difficult to carry out industrialized production, relatively high cost and low yield. The theoretical yield can reach 50%, but the yield in actual application is only 10%-20%. Therefore, the application Such methods are very expensive to produce. Sometimes the chemical resolution method als...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C12P13/04
Inventor 洪浩郑长胜高峰李雁飞吕丽慧吕彤李艳君
Owner ASYMCHEM LAB TIANJIN
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