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Method for catalytically preparing optically pure (S)-(+)-2-phenylpropionic acid with Rhodococcus ruber 4.1187

A technology for the preparation of phenylpropionic acid and catalysis, which is applied in the direction of biochemical equipment and methods, bacteria, and methods based on microorganisms, can solve the problem of less 2-phenylpropionic acid, and achieve mild reaction conditions, environmental friendliness, and special strong effect

Inactive Publication Date: 2010-11-24
EAST CHINA UNIV OF SCI & TECH
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  • Abstract
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  • Claims
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AI Technical Summary

Problems solved by technology

[0008] 2-Phenylpropionic Acid (2-Phenylpropionic Acid) is an important 2-arylpropionic acid substance. Currently, it is mainly prepared by chemical resolution, while (S)-(+)-2- There are few reports on phenylpropionic acid at home and abroad

Method used

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  • Method for catalytically preparing optically pure (S)-(+)-2-phenylpropionic acid with Rhodococcus ruber 4.1187
  • Method for catalytically preparing optically pure (S)-(+)-2-phenylpropionic acid with Rhodococcus ruber 4.1187
  • Method for catalytically preparing optically pure (S)-(+)-2-phenylpropionic acid with Rhodococcus ruber 4.1187

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Embodiment Construction

[0019] Case 1

[0020] Add 10g Rhodococcus ruber 4.1187 resting cells to 100mL buffer (pH 7.5Tris-HCl, 100mM), the substrate concentration of racemic 2-phenylpropanamide is 20mM (0.30g), and the cosolvent DMSO (5% ), at 30°C, 180rpm in a shaker, the reaction was completed for 3h. The cells were removed by centrifugation, and the supernatant was adjusted to pH 12 with sodium hydroxide solution, extracted three times with the same volume of ethyl acetate, washed with saturated saline, dried over anhydrous sodium sulfate, and concentrated to obtain (R)-(-)-2- Phenylpropanamide; the pH value of the aqueous phase was adjusted to 2 with 2M hydrochloric acid, and the remaining operations were the same as above, and concentrated to obtain (S)-(+)-2-phenylpropionic acid.

[0021] Finally, the yield of product (S)-(+)-2-phenylpropionic acid is 48%, e.e. is 98.5%; the yield of residual substrate (R)-(-)-2-phenylpropanamide is 49% %, e.e. 98%.

[0022] Case 2

[0023] Add 10g of Rhodo...

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Abstract

The invention discovers Rhodococcus ruber 4.1187 which can be used for efficiently catalytically preparing optically pure (S)-(+)-2-phenylpropionic acid. The invention has the advantages of mild reaction conditions and environment-friendliness. The prepared optically pure (S)-(+)-2-phenylpropionic acid is an important 2-arylpropionic acid non-steroidal anti-inflammatory drug or an important chiral building block. The chemical formulas of (5)-(+)-2-phenylpropionic acid and (R)-(-)-2-phenyl-propionamide are shown in the specification.

Description

technical field [0001] The invention relates to a preparation method of single-configuration (S)-(+)-2-phenylpropionic acid, which belongs to the field of bioorganic synthesis. The substance is the most basic 2-aryl propionic acid non-steroidal anti-inflammatory Drugs, and can be used as chiral building blocks to further synthesize chiral drugs. Background technique [0002] 2-arylpropionic acid is a class of widely used non-steroidal anti-inflammatory drugs, such as ibuprofen (Ibupmfen), naproxen (Naproxen), ketoprofen (Ketoprofen) etc. (Figure 1), has excellent Antipyretic, anti-inflammatory and analgesic effects. The S configuration of these anti-inflammatory drugs is generally more active than the R configuration, and has less side effects. For example, the anti-inflammatory and analgesic effect of the S configuration of naproxen is 28 times higher than that of the R configuration; the analgesic effect of S-ibuprofen is higher than that of the R configuration - 100 tim...

Claims

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Application Information

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IPC IPC(8): C12P41/00C12P7/40C12P13/02C12N1/20C12R1/01
Inventor 任玉杰张红卫许建和
Owner EAST CHINA UNIV OF SCI & TECH
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