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Resolution of mandelic acid with chiral resin containing magnetic nanoparticles

2012
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Advisor: Doç. Dr. Bilsen Tural ; Prof. Dr. Giray Topal

Abstract (EN)

In this study, the resolution of (R)- and (S)-mandelic acid, which is pharmacologically important, was provided. For many years, (R)-mandelic acid has widely been used antibacterial infections, especially treatment of urinary tract in the medicine, treatment of skin diseases, skin care products, to resolve the problems of acne in adults, for rosacea (rose-disease), to relieving inflamation and rashes. Importantly (R)-mandelic acid is a key intermediate for the production of semi-synthetic cephalosporins and penicillins. It is also used as a chiral resolving agent and chiral synthon for the synthesis of anti-tumor and anti-obesity agents and also to increasing the activity of the drug antibiotic. (S)-mandelic acid is mostly used for animal health and in animal care medicine. It is important to ensure the resolution of these two enantiomers having different pharmacological effects.In this study a resin was synthesized, which contain for separating suitable chiral groups then it was bound to covalent on silica-coated magnetic nanoparticles (Fe3O4). And then racemic mixture of mandelic acid was prepared and dissolved in phosphate solution of different pH levels ( pH 2.2; 3.5; 4.0; 4.4 ?). The racemic mixture obtained was interacted with contain magnetic nanoparticles resin via a mechanic mixer. In different periods of time eluateds obtained was extracted together with the ether(diethylether) and ether phase was evaporated. Then remaining white solid material was in n-hexane-isopropanol mixture analyzed by HPLC and calculated enantiomeric excess (e,e).The studies enantiomeric separation made using magnetic nanoparticles very rarely encountered in the literature, which were published in 2010 and in the following years. Our goal, with this method is to contribute this kind of studies, which may be a new glimmer of hope in the future.

Author

Tuba Tarhan

How to Cite

Tuba Tarhan (Master Thesis). Resolution of mandelic acid with chiral resin containing magnetic nanoparticles, 2012, Dicle University.

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