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Preparation technology of chiral amino acid

A technology of chiral amino acid and preparation process, which is applied in fermentation and other directions, can solve the problems of low efficiency and incomplete resolution of enzyme resolution, and achieve the effect of increasing acetylation content and resolution effect

Active Publication Date: 2013-08-07
滨海瀚鸿生化有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The technical problem to be solved by the present invention is to provide a chiral amino acid in order to overcome defects such as low efficiency of enzymatic resolution and incomplete resolution in the existing method for splitting and producing chiral amino acids by aminoacylase preparation process

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] 200 kilograms of acetylated-DL-phenylalanine prepared in comparative example 1, feed concentration 92% (HPLC content), add toluene 200L, and mass concentration 30% methylamine solution 500 kilograms, then heat up temperature 80-90 degree (external temperature), maintained for 2 hours, and then distilled under reduced pressure at -0.01MPa and 70°C for 5 hours, then added water to adjust the pH to 7.5, and the content determined by HPLC was 98%, and directly added D-amino acid acylase 3 grams split, and the split reached the end point after 72 hours. Concentrate the reaction liquid to a small volume, lower the temperature, crystallize, and filter to obtain D-phenylalanine with a white appearance, a content of 99%, a chiral content of 99.7%, and a qualified quality. Concentrate the filtrate to a small volume, adjust the pH to 2, crystallize to obtain acetylated-L-phenylalanine, add 0.3M hydrochloric acid to reflux and hydrolyze for 2 hours, recover the hydrochloric acid, a...

Embodiment 2

[0028] Using DL-norleucine as the raw material, using the same molar ratio as that of Comparative Example 1, the reaction temperature was 110°C, the reaction time was 5 hours, the pressure was -0.1Mpa, and the external temperature was 90°C for 5 hours to distill glacial acetic acid. After crystallization The DL-norleucine content of acetylated norleucine detected by HPLC is 88%; Toluene is added in acetylated norleucine (the volume of toluene is 5 times of the mass of acetylated norleucine, L / Kg), then add 5 times Volume (the mass ratio of volume to acetylated norleucine is 5L / Kg) 30% methylamine solution, the temperature is raised to 80-90 (external temperature) degrees, maintained for 2 hours, and then under the pressure of -0.05MPa, the external temperature Distill under reduced pressure at 95°C for 5 hours, then add water, adjust the pH to 7.5, and measure the content to 99%, directly add 5 g of D-amino acid acylase for resolution, and the resolution will reach the end poin...

Embodiment 3

[0030] Using L-valine as raw material, using the same molar ratio as that of Comparative Example 1, the reaction temperature is 110 degrees, the reaction time is 5 hours, the pressure is -0.5Mpa, and the external temperature is 70 ° C. Distill glacial acetic acid for 3 hours, and HPLC after crystallization Detect acetylated valine content 80%; Add toluene (the volume of toluene is 3 times of acetylated valine mass, L / Kg) in acetylated valine, after adding 5 times of 30% methylamine solution again, Raise the temperature to 80-90 degrees, keep it for 2 hours, then under the pressure of -0.08MPa, distill under reduced pressure at an external temperature of 75°C for 5 hours, then add water, adjust the pH to 7.5, and measure the content to 97%, directly add D-amino acid acylation 5 grams of enzymes were split, and the split reached the end point after 72 hours. Concentrate and filter the crystals to obtain D-valine with a white appearance, a content of 99%, qualified quality, and a...

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Abstract

The invention discloses a preparation technology of chiral amino acid, comprising the following steps of: 1) performing acetylation between L-amino acid or DL-amino acid and acetic anhydride; 2) distilling the reactant obtained from the step 1), and cooling for crystallization; 3) mixing acetylated L-amino acid or acetylated DL-amino acid obtained from the step 2), toluene and a methylamine aqueous solution, an ethylamine aqueous solution or a caustic soda flake aqueous solution until the temperature reaches 80-90 DEG C, maintaining for 1.5-2.5 hours, distilling at minus 0.001-minus 0.1 MPa at 50-95 DEG C for 4-6 hours, adding water, and adjusting pH to 7-8; and 4) carrying out resolution on the substance obtained from the step 3) and D-aminoacylase or L-aminoacylase. By the preparation technology provided by the invention, impurities in the method for resolution of chiral amino acid from aminoacylase can be effectively removed, acetylation content can be raised, and the resolution effect can be obviously improved in comparison with the prior art.

Description

technical field [0001] The invention specifically relates to a preparation process of a chiral amino acid. Background technique [0002] Aminoacylase splitting to produce amino acid is the main process for the production of amino acid, especially unnatural amino acid. The operation process is generally that L-amino acid or DL-amino acid is reacted with acetic anhydride at high temperature under the solvent of glacial acetic acid to prepare acetylated-DL-amino acid, and then the acetylated-DL-amino acid is formulated into a solution of pH7.5-8.0 , add aminoacylase, acetylation-DL-amino acid is converted into D- or L-amino acid. The aminoacylases used include two enzymes, D-aminoacylase and L-aminoacylase, both of which are commercially available, and there are immobilized aminoacylases. [0003] Aminoacylase splits and produces amino acids, and whether the catalytic activity of the acylase can be fully exerted and the conversion rate can be improved are the main technical i...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C12P41/00
Inventor 马士忠刘明君查正兴谢建曾磊胡文进
Owner 滨海瀚鸿生化有限公司
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