Chiral capillary electrophoresis applied to the determination of phenylglycidol enantiomers obtained from cinnamyl alcohol by asymmetric epoxidation using new titanium(IV) alkoxide compounds as catalysts

被引:18
|
作者
Morante-Zarcerol, S
Crego, AL
Sierra, I
Fajardo, M
Marina, ML
机构
[1] Univ Alcala de Henares, Fac Quim, Dept Quim Analit, E-28871 Alcala De Henares, Spain
[2] Univ Rey Juan Carlos, ESCET, Dept Tecnol Quim Ambiental & Mat, Madrid, Spain
关键词
asymmetric epoxiclation / Chiral capillary electrophoresis; cinnamyl alcohol; phenylglycidol enantiomers;
D O I
10.1002/elps.200405934
中图分类号
Q5 [生物化学];
学科分类号
071010 ; 081704 ;
摘要
A capillary electrophoresis method for the simultaneous determination of phenylglycidol enantiomers in the presence of an excess of cinnamyl alcohol was developed. The effects of the nature, pH and concentration of the buffer, the nature and concentration of chiral selector, the addition of methanol or acetonitrile, and the capillary temperature on the chiral resolution of phenylglycidol enantiomers were studied. Separations were achieved using 20 mm succinylated P-cyclodextrin dissolved in a 10 mm borate buffer (pH 10.0). Chiral resolution for the phenylglycidol enantiomers in the optimized electrophoretic conditions was higher than 2.0 with an analysis time less than 7 min. The method developed was validated in terms of selectivity, linearity, precision (instrumental repeatability, method repeatability, intermediate precision), the limits of detection and quantitation, and accuracy. Limits of detection of 6.5 mg/L and 8.3 mg/L for (2S,3S)-(-)-3-phenylglycidol ((S,S)-PG) and (2R,3R)-(+)-3-phenylglycidol ((R,R)-PG), respectively, were obtained. The method was applied to study the asymmetric epoxidation of cinnamyl alcohol with titanium(IV) alkoxide compounds as catalysts in order to evaluate their catalytic activity and stereoselectivity of the epoxidation processes.
引用
收藏
页码:2745 / 2754
页数:10
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  • [1] Simultaneous determination of phenylglycidol enantiomers and cinnamyl alcohol in asymmetric epoxidation processes by chiral liquid chromatography
    Morante-Zarcero, S
    Pérez, Y
    del Hierro, I
    Fajardo, M
    Sierra, I
    JOURNAL OF CHROMATOGRAPHY A, 2004, 1046 (1-2) : 61 - 66