Synthesis of dendritic stationary phases with surface-bonded L-phenylalanine derivate as chiral selector and their evaluation in HPLC resolution of racemic compounds.

Chuan-Qi Yin, Bao-Jiang He, Shao-Hua Huang, Jun-Yi Zhang, Zheng-Wu Bai, Zao-Ying Li

Index: Chirality 20(7) , 846-55, (2008)

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Abstract

Four dendrimers were synthesized on aminopropyl-modified silica gel using methyl acrylate and ethylene diamine as building blocks by divergent method. Four generations of chiral stationary phases (CSPs) were prepared by coupling of L-2-(p-toluenesulfonamido)-3-phenylpropionyl chloride to corresponding dendrimers. The derivatives prepared on silica gel were characterized by FT-IR, (1)H NMR, and elemental analysis. The selector loadings of these four generations of CSPs generally showed a decrease tendency with the increase of generation numbers of dendrimers. The enantioseparation properties of these CSPs were preliminarily investigated by high-performance liquid chromatography. The CSP derived from the three-generation dendrimer exhibited the best enantioseparation capability. Effects of the mobile phase composition and molecular structures of racemic mixtures on enantioseparation were further studied.Copyright 2008 Wiley-Liss, Inc.