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以硫酸化β-环糊精作为手性选择剂,在有和没有硼酸盐络合的情况下,通过毛细管区带电泳对氢化苯偶姻及结构相关化合物进行对映体拆分的比较研究。

Comparative studies on the enantioseparation of hydrobenzoin and structurally related compounds by capillary zone electrophoresis with sulfated beta-cyclodextrin as the chiral selector in the presence and absence of borate complexation.

作者信息

Lin Sheng-Li, Lin Ching-Erh

机构信息

Department of Chemistry, National Taiwan University, Taipei 10674, Taiwan.

出版信息

J Chromatogr A. 2004 Apr 2;1032(1-2):213-8. doi: 10.1016/j.chroma.2003.11.100.

DOI:10.1016/j.chroma.2003.11.100
PMID:15065798
Abstract

Comparative studies on the enantioseparations of racemic hydrobenzoin, together with benzoin and benzoin methyl ether, in capillary zone electrophoresis using sulfated beta-cyclodextrin (S-beta-CD) as a chiral selector in the presence and absence of borate complexation were investigated. The influences of S-beta-CD concentration on the enantioseparation of benzoins in a borate buffer and a phosphate background electrolyte and the influences of the concentration and the pH of borate buffer containing S-beta-CD on the enantioseparation of hydrobenzoin were examined. The results indicate that, depending on the degree of strong borate complexation and comparatively weak CD complexation, the selectivity of the enantiomers of hydrobenzoin can be greatly reduced in a buffer system containing borate ions. Enantioseparation of hydrobenzoin is mainly governed by the interaction between hydrobenzoin-borate complexes and S-beta-CD in a borate buffer, whereas enantioseparation of benzoins is primarily determined by CD complexation in a phosphate background electrolyte. Effective enantioseparations of benzoins were simultaneously achieved with addition of S-beta-CD at a concentration greater than 3.0% (w/v) in a borate buffer and at a concentration greater than 2.5% (w/v) in a phosphate background electrolyte at pH 9.0.

摘要

研究了在有和没有硼酸盐络合作用的情况下,使用硫酸化β-环糊精(S-β-CD)作为手性选择剂,在毛细管区带电泳中对消旋氢化苯偶姻以及苯偶姻和苯偶姻甲醚进行对映体分离的比较研究。考察了S-β-CD浓度对硼酸盐缓冲液和磷酸盐背景电解质中苯偶姻对映体分离的影响,以及含S-β-CD的硼酸盐缓冲液的浓度和pH值对氢化苯偶姻对映体分离的影响。结果表明,根据硼酸盐强络合程度和相对较弱的环糊精络合程度,在含硼酸盐离子的缓冲体系中,氢化苯偶姻对映体的选择性会大大降低。在硼酸盐缓冲液中,氢化苯偶姻的对映体分离主要受氢化苯偶姻-硼酸盐络合物与S-β-CD之间相互作用的影响,而在磷酸盐背景电解质中,苯偶姻的对映体分离主要由环糊精络合作用决定。在pH 9.0的硼酸盐缓冲液中加入浓度大于3.0%(w/v)的S-β-CD以及在磷酸盐背景电解质中加入浓度大于2.5%(w/v)的S-β-CD时,可同时实现苯偶姻的有效对映体分离。

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