Chiral separation of newly synthesized arylpropionic acids by capillary electrophoresis using cyclodextrins or a glycopeptide antibiotic as chiral selectors |
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Authors: | S Fanali C Cartoni C Desiderio |
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Institution: | (1) Istituto di Cromatografia del CNR, Area della Ricerca di Roma, P.O. Box 10, 00016 Monterotondo Scalo, Roma, Italy |
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Abstract: | Summary The chiral separation of two newly synthesized arylpropionic acids of pharmaceutical interest, namely 2-(5′-benzoil-2′-hydroxy)phenyl]-propionic
acid (DF-1738y) and 2-(4′-benzoiloxy-2′-hydroxy)phenyl]-propionic acid (DF-1770y), was performed by Capillary Zone Electrophoresis
(CZE) using either cyclodextrins or antibiotics as chiral selectors in coated capillary. In order to optimize the separation,
the effect on the migration time and resolution of type and concentration of the chiral selector, the buffer pH and the capillary
temperature were studied. Several cyclodextrins, namely the charged 6A-monomethylamino-β-cyclodextrin (MeNH-β-CD) and the neutral methyl-β-cyclodextrins (M-β-CD) and heptakis-2,3,6-tri-O-methyl-β-cyclodextrin
(TM-β-CD), were tested for the enantiomeric separation of aryl propionic acids (APAs) compounds. Of these TM-β-CD provided
the highest enantiomeric resolution at pH 5, however only DF-1738y optical isomers were baseline resolved. Using background
electrolytes (BGEs) at higher pHs (pH=6–7) supported with the above listed CDs, an enantioresolution increase was recognized
only for compound DF-1738y. In contrast DF-1770y exhibited the highest resolution at the lowest pH value studied (pH 4). The
macrocyclic antibiotic vancomycin was therefore added to the BGE and tested as chiral selector using the partial filling counter
current mode in order to obtain a sensitive analysis, high resolution and reduced antibiotic adsorption on the capillary wall.
5 mM vancomycin dissolved in the BGE at pH 5 and 25°C provided relatively high enantiomeric resolution (R
DF-1738y=3.4,R
DF-1770y=2.22) of both compounds. |
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Keywords: | Capillary electrophoresis Arylproprionic acids Chiral resolution Cyclodextrins Vancomycin |
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