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      Enantioselective extraction of ketoprofen enantiomers using ester alcohol R, R-di-tartarates or S, S-di-tartarates as chiral selector

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          Abstract

          Distribution behavior of ketoprofen enantiomers was examined in a two-phase system containing R, R-di-tartarates or S, S-di-tartarates. The influences of different alkyl chain of R, R-di-tartarates or S, S-di-tartarates, concentrations of R, R-di-tartarate, organic solvent and content of methanol on partition coefficient and separation factor were investigated, respectively. The experimental results show that R, R-di-tartarates studied all form more stable diastereomeric complexes with ketoprofen S-enantiomer than with R-enantiomer. The partition coefficients and enantioselectivity generally increase with the addition of length of alkyl chain of alcohol. The concentration of chiral selector and methanol also have bigger influences on enantioselectivity.

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          Most cited references37

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          Microbial lipases form versatile tools for biotechnology.

          K. Jaeger (1998)
          Lipases are secreted into the culture medium by many bacteria and fungi. They catalyse not only the hydrolysis but also the synthesis of long-chain acylglycerols. Important uses in biotechnology include their addition to detergents, the manufacture of food ingredients, pitch control in the pulp and paper industry, and biocatalysis of stereoselective transformations. This makes them the most widely used class of enzymes in organic chemistry. Immobilization in hydrophobic sol-gel matrices and in vitro evolution are promising novel approaches to increasing the stability or enantioselectivity, respectively, of lipases.
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            Preparation of enantiopure (S)-ketoprofen by immobilized Candida rugosa lipase in packed bed reactor

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              Production of optically active ketoprofen by direct enzymatic esterification.

              For the production of optically active ketoprofen, enzymatic resolution of racemic ketoprofen in an organic solvent has been accomplished via enantioselective esterification. Pharmacologically inactive (R)-ketoprofen is converted into the corresponding (R)-ester by this method. Enantioselectivity in lipase-catalyzed resolution of racemic ketoprofen was mainly dependent on the sources of lipase, alcohol moiety, organic solvent, and water content. Ethanol was used as the alkyl donor and the optimum water content required for highly efficient enzymatic resolution was determined to be 0.1-0.15% (v/v), which was maintained using salt hydrates such as Na2SO4 x 10H2O. (S)-Ketoprofen could be obtained with high enantioselectivity (E=15) in n-hexane supplemented with ethylene dichloride (20% (v/v)) using commercially available Candida antarctica lipase (Novozym 435).
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                Author and article information

                Contributors
                Role: ND
                Role: ND
                Role: ND
                Role: ND
                Role: ND
                Journal
                laar
                Latin American applied research
                Lat. Am. appl. res.
                Universidad Nacional del Sur y Consejo Nacional de Investigaciones Científicas y Técnicas (Bahía Blanca, Buenos Aires, Argentina )
                0327-0793
                1851-8796
                July 2006
                : 36
                : 3
                : 187-191
                Affiliations
                [01] Changsha orgnameCentral South University orgdiv1School of Chemistry and Chemical Engineering China
                Article
                S0327-07932006000300009
                9df3f992-cbc2-42e3-8314-2d0b78b5a95a

                This work is licensed under a Creative Commons Attribution-NonCommercial 4.0 International License.

                History
                : 31 May 2006
                : 28 April 2006
                Page count
                Figures: 0, Tables: 0, Equations: 0, References: 32, Pages: 5
                Product

                SciELO Argentina


                Separation Factor,Chiral Selector,Ketoprofen Enantiomers,Partition Coefficient,Enantioselective Extraction

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