RT info:eu-repo/semantics/article
T1 Enantioselective separation of azole compounds by EKC. Reversal of migration order of enantiomers with CD concentration: research article
A1 Castro Puyana, María
A1 Crego Navazo, Antonio Luis
A1 Marina Alegre, María Luisa
A1 García Ruiz, Carmen
K1 Apparent binding constants
K1 Azole compounds
K1 Enantioseparation
K1 EKC
K1 Ciencia
K1 Química analítica e industrial
K1 Science
K1 Chemistry, analytic and technical
AB The enantioselective separation of a group of six weak base azole compounds was achieved in this work using EKC with three neutral beta-CDs as chiral selectors. The native beta-CD and two other beta-CD derivatives with different types and positions of the substituents on the CD rim ((2-hydroxy)propyl-beta-CD (HP-beta-CD) and heptakis-2,3,6-tri-O-methyl-beta-CD (TM-beta-CD)) were employed. Apparent binding constants for each pair compound-CD were determined in order to study analyte-CD interactions. The best enantiomeric resolutions for miconazole, econazole, and sulconazole were observed with HP-beta-CD whereas for the separation of the enantiomers of ketoconazole, terconazole, and bifonazole, TM-beta-CD was the best chiral selector. The enantioseparations obtained were discussed on the basis of the structure of the compounds taking into account that inclusion into the hydrophobic CD cavity occurred through the phenyl ring closer to the azole group. In addition, a change in the migration order for the enantiomers of two of the compounds studied (ketoconazole and terconazole) with the concentration of HP-beta-CD was observed for the first time.
PB John Wiley & Sons
SN 0173-0835
YR 2007
FD 2007
LK http://hdl.handle.net/10017/1345
UL http://hdl.handle.net/10017/1345
LA eng
NO The authors thank the Ministerio de Ciencia y Tecnología and the Ministerio de Educación y Ciencia (Spain) for research projects BQU2003-03638 and CTQ2006-03849/BQU, respectively. Authors also thank Johnson & Johnson (Beerse, Belgium) for the kind gift of terconazole racemate and pure 2R,4S-enantiomer of the ketoconazole. Carmen García-Ruiz thanks the Ministerio de Ciencia y Tecnología (Spain) for the Ramón y Cajal program (RYC-2003-001). María CastroPuyana thanks the University of Alcalá for her predoctoral grant
DS MINDS@UW
RD 20-abr-2024