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Method for preparing S-ibuprofen and S-ibuprofen ester by biological catalysis

A technology of ibuprofen axetil and mixture, applied in the field of high optical purity S-ibuprofen and S-ibuprofen axetil, can solve the problems of unsatisfactory, low catalytic conversion rate stereoselectivity and the like

Inactive Publication Date: 2008-01-16
BEIJING UNIV OF CHEM TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Enzymes currently used for enantiomeric resolution of racemic ibuprofen include lipases from Rhizomucor miehei, Candida rugosa, Candida antarctica (Novozyme 435), Aspergillus niger AC-54 and Thermomyces lanuginosa, etc., but the catalytic conversion of these enzymes efficiency and stereoselectivity are low, unsatisfactory (see: Fabiano Jares Contesini and Patrl'cia de Oliveira Carvalho * Esterification of(RS)-Ibuprofen by native and commercial lipases in a two-phase system containing ionic liquidsTetrahedron: Asymmetry 17(2006)2069-2073)

Method used

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  • Method for preparing S-ibuprofen and S-ibuprofen ester by biological catalysis
  • Method for preparing S-ibuprofen and S-ibuprofen ester by biological catalysis
  • Method for preparing S-ibuprofen and S-ibuprofen ester by biological catalysis

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preparation example Construction

[0017]The preparation of the immobilized enzyme of the present invention can be referred to the applicant's co-pending Chinese invention patent application No. 200510112638.5. In addition, the preparation of crude enzymes, immobilized enzymes, modified enzymes, and enzyme fermentation broths used in the present invention are also taught in the following documents: Tan TW, Zhang M, Wang BW, Ying CH, Deng L. Screening of high lipase producing Candida sp. and production of lipase by fermentation. Process Biochem 2003, 39(4): 459-65; Mingrui Yu, Shaowei Qin, Tianwei Tan, Purification and characterization of the extracellular lipase Lip2 from Yarrowia lipolytica, Process Biochemistry 4 (2007) 384-391; Kaili Nie, Feng Xie, Fang Wang, TianweiTan, Lipase catalyzed methanolysis to produce biodiesel: Optimization of the biodiesel production. Journal of Molecular Catalysis B: Enzymatic 43(2006) 142-147; and Chinese Invention Patent Application No. 02017614. , its publication number is CN...

Embodiment 1

[0041]In a 100ml Erlenmeyer flask with a stopper, 10ml of n-hexane solution of racemic ibuprofen (purchased from Sigma, the same below) with a concentration of 0.03mol / L, 0.3mmol of ethanol, and 0.2g of immobilized enzyme were sequentially added. The immobilized enzyme refers to the applicant's co-pending Chinese invention patent application No.200510112638.5 and Tan TW, Zhang M, Wang BW, Ying CH, Deng L.Screening of high lipase producing Candida sp.and production of lipase byfermentation.Process Prepared by the method in Biochem 2003; 39(4): 459-65, hereinafter the same. The reaction mixture was placed on a shaker at 40°C, shaken and incubated at a speed of 180 rpm for 24 hours to obtain a mixture containing racemic ibuprofen, S-ibuprofen ethyl ester, R-ibuprofen ethyl ester mixture. Take 20 microliters of the above mixture for analysis, the analysis method is as follows:

[0042] Detection by high performance liquid chromatography (chiral column: CHIRALCEL OB ~ H, 15cm × 4...

Embodiment 2

[0050] In a 100 ml Erlenmeyer flask with a stopper, 10 ml of a 0.03 mol / L racemic ibuprofen n-hexane solution, 0.6 mmol of ethanol, and 0.2 g of immobilized enzyme were sequentially added. Reaction, detection, separation and hydrolysis under the same conditions as in Example 1, the results are as follows: the conversion rate c is 0.396, the excess value ees=0.606 of the substrate enantiomer, and the stereoselectivity E=47.22 of the enzyme (the maximum of the enzyme) Preferable selectivity is S type).

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Abstract

The invention provides a novel catalytic synthesis method to produce s-ibuprofen and various s-ibuprofen esters. S-ibuprofen ester is obtained by esterifying racemic ibuprofen and alcohol with the extracellular lipase deriving from yarrowia lipolytica. The invention further relates to the method of hydrolyzing the synthesized s-ibuprofen ester to prepare s-ibuprofen.

Description

technical field [0001] The invention belongs to the field of biotechnology, relates to the method for preparing S-ibuprofen and S-ibuprofen ester, more specifically, relates to utilizing lipase to catalyze the splitting of racemic ibuprofen to obtain S-ibuprofen with high optical purity - Method of ibuprofen and S-ibuprofen ester. Background technique [0002] Non-steroidal anti-inflammatory drugs (non-steroidal anti-inflammatory drugs, NSAIDs) are a class of drugs that have antipyretic, analgesic, and most of them also have anti-inflammatory and anti-rheumatic effects, and are widely used clinically to treat rheumatoid arthritis. Inflammation, osteoarthritis and other rheumatic diseases, relieve the suffering of hundreds of millions of rheumatic patients. This class of drugs mainly includes racemic ibuprofen (racemic-2-(4-isobutylphenyl)propionic acid), flurbiprofen (rac-2-((3-fluoro-4- Phenyl)phenyl)propionic acid, fenoprofen (racemic-2-(3-phenoxyphenyl)propionic acid), ...

Claims

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Application Information

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IPC IPC(8): C12P7/62C12P7/40C07C51/09C12R1/72
Inventor 谭天伟刘英王芳
Owner BEIJING UNIV OF CHEM TECH
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