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Lipase-mediated enantioselective kinetic resolution of racemic acidic drugs in non-standard organic solvents: Direct chiral liquid chromatography monitoring and accurate determination of the enantiomeric excesses

Citation

Ghanem, A and Aboul-Enein, MN and El-Azzouny, A and El-Behairy, MF, Lipase-mediated enantioselective kinetic resolution of racemic acidic drugs in non-standard organic solvents: Direct chiral liquid chromatography monitoring and accurate determination of the enantiomeric excesses, The Journal of Chromatography A, 1217, (7) pp. 1063-1074. ISSN 0021-9673 (2010) [Refereed Article]


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DOI: doi:10.1016/j.chroma.2009.10.080

Abstract

The enantioselective resolution of a set of racemic acidic compounds such as non-steroidal anti-inflammatory drugs (NSAIDs) of the group arylpropionic acid derivatives is demonstrated. Thus, a set of lipases were screened and manipulated in either the esterification or hydrolysis mode for the enantioselective kinetic resolution of these racemates in non-standard organic solvents. The accurate determination of the enantiomeric excesses of both substrate and product during such reaction is demonstrated. This was based on the development of a direct and reliable enantioselective high performance liquid chromatography (HPLC) procedure for the simultaneous baseline separation of both substrate and product in one run without derivatization. This was achieved using the immobilized chiral stationary phase namely Chiralpak IB, a 3,5-dimethylphenylcarbamate derivative of cellulose (the immobilized version of Chiralcel OD) which proved to be versatile for the monitoring of the lipase-catalyzed kinetic resolution of racemates in non-standard organic solvents.

Item Details

Item Type:Refereed Article
Keywords:Chiralpak IB; Enantiomeric Excess; Enantioselective HPLC; Direct Monitoring; Kinetic Resolution; Lipase; Racemic Acidic Drugs
Research Division:Chemical Sciences
Research Group:Analytical Chemistry
Research Field:Separation Science
Objective Division:Expanding Knowledge
Objective Group:Expanding Knowledge
Objective Field:Expanding Knowledge in the Chemical Sciences
Author:Ghanem, A (Dr Ashraf Ghanem)
ID Code:59005
Year Published:2010
Web of Science® Times Cited:28
Deposited By:Austn Centre for Research in Separation Science
Deposited On:2009-11-12
Last Modified:2011-05-04
Downloads:0

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