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1-(α-氨基苄基)-2-萘酚和2-(α-氨基苄基)-1-萘酚类似物在高效液相色谱对映体分离中的结构和温度效应

Structural and temperature effects in the high-performance liquid chromatographic enantioseparation of 1-(alpha-aminobenzyl)-2-naphthol and 2-(alpha-aminobenzyl)-1-naphthol analogs.

作者信息

Sztojkov-Ivanov Anita, Szatmári István, Péter Antal, Fülöp Ferenc

机构信息

Institute of Pharmaceutical Chemistry, University of Szeged, Szeged, Hungary.

出版信息

J Sep Sci. 2005 Dec;28(18):2505-10. doi: 10.1002/jssc.200500138.

DOI:10.1002/jssc.200500138
PMID:16405181
Abstract

The enantiomers of 1-(alpha-aminobenzyl)-2-naphthol and 2-(alpha-aminobenzyl)-1-naphthol analogs were separated isothermally on a cellulose-tris-3,5-dimethylphenyl carbamate-based chiral stationary phase (Chiralcel OD-H), at 10 degrees C increments in the range of 5-35 degrees C, using n-hexane/2-propanol/diethylamine as mobile phase. The mobile phase composition and temperature were varied to achieve baseline resolutions in a single chromatographic run. The dependence of the natural logarithms of selectivity factors, In alpha, on the inverse of temperature, 1/T, was used to determine the thermodynamic data of the enantiomers. The thermodynamic data revealed that all the compounds in this study separate via the same enthalpy-driven chiral recognition mechanism.

摘要

在基于纤维素-三(3,5-二甲基苯基)氨基甲酸酯的手性固定相(Chiralcel OD-H)上,以正己烷/2-丙醇/二乙胺为流动相,在5至35℃范围内以10℃的增量等温分离1-(α-氨基苄基)-2-萘酚和2-(α-氨基苄基)-1-萘酚类似物的对映体。改变流动相组成和温度以在一次色谱运行中实现基线分离度。利用选择性因子的自然对数lnα对温度倒数1/T的依赖性来确定对映体的热力学数据。热力学数据表明,本研究中的所有化合物均通过相同的焓驱动手性识别机制进行分离。

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引用本文的文献

1
High-performance liquid chromatographic enantioseparation of Betti base analogs on a newly developed isopropyl carbamate-cyclofructan6-based chiral stationary phase.新型异丁基氨基甲酸酯-环果糖 6 衍生手性固定相对 betti 碱基类似物的高效液相色谱对映体拆分。
Chirality. 2011 Aug;23(7):549-56. doi: 10.1002/chir.20968. Epub 2011 Jun 16.