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新型固定化 3,5-二甲基苯甲酰氨基多糖手性固定相的合成及其对映体拆分行为。

Synthesis and enantioseparation behaviors of novel immobilized 3,5-dimethylphenylcarbamoylated polysaccharide chiral stationary phases.

机构信息

School of Chemistry and Environment, South China Normal University, Guangzhou, P.R. China.

出版信息

J Sep Sci. 2014 Mar;37(5):488-94. doi: 10.1002/jssc.201301146. Epub 2014 Jan 22.

DOI:10.1002/jssc.201301146
PMID:24376089
Abstract

Two new polysaccharide-derived chiral selectors, namely, 6-azido-6-deoxy-3,5-dimethylphenylcarbamoylated amylose and 6-azido-6-deoxy-3,5-dimethylphenyl carbamoylated cellulose, were synthesized under homogeneous conditions and immobilized onto aminized silica gel by the Staudinger reaction, resulting in two new immobilized polysaccharide chiral stationary phases (CSPs). Their enantioseparation performances were investigated under normal-phase mode by HPLC. Among 17 analytes, baseline separations of 12 pairs of enantiomers are achieved on the immobilized cellulose CSP, which demonstrates that this new cellulose material exhibits almost the same enantioseparation performance as the coated cellulose CSP. In addition, the amylose-derived CSP presents limited enantiorecognition ability but certain complementarity with the immobilized and coated cellulose-based materials. Neither metolachlor nor paclitaxel side chain acids are separated on two cellulose-derived CSPs, but effective separations are obtained on the immobilized amylose column.

摘要

两种新的多糖衍生手性选择体,即 6-叠氮-6-脱氧-3,5-二甲基苯甲酰氨基化淀粉和 6-叠氮-6-脱氧-3,5-二甲基苯甲酰氨基化纤维素,在均相条件下合成,并通过 Staudinger 反应固定到氨化硅胶上,得到两种新的固定化多糖手性固定相(CSP)。通过 HPLC 在正相模式下研究了它们的对映体分离性能。在 17 种分析物中,12 对对映异构体在固定化纤维素 CSP 上实现了基线分离,这表明这种新型纤维素材料表现出几乎与涂层纤维素 CSP 相同的对映体分离性能。此外,淀粉衍生的 CSP 表现出有限的对映体识别能力,但与固定化和涂层的纤维素基材料具有一定的互补性。两种纤维素衍生的 CSP 均不能分离甲草胺和紫杉醇侧链酸,但在固定化淀粉柱上可有效分离。

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