Synthesis of dendritic stationary phases with surface-bonded L-phenylalanine derivate as chiral selector and their evaluation in HPLC resolution of racemic compounds.
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.
Yin
Chuan-Qi
CQ
College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, Hubei Province, China.
He
Bao-Jiang
BJ
Huang
Shao-Hua
SH
Zhang
Jun-Yi
JY
Bai
Zheng-Wu
ZW
Li
Zao-Ying
ZY
D002851:Chromatography, High Pressure Liquid / Q000379:methods*; D050091:Dendrimers / Q000138:chemical synthesis* / Q000737:chemistry; D005029:Ethylenediamines / Q000737:chemistry; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010649:Phenylalanine / Q000737:chemistry*; D058428:Silica Gel; D012822:Silicon Dioxide; D017550:Spectroscopy, Fourier Transform Infrared; D013237:Stereoisomerism; D013449:Sulfonamides / Q000737:chemistry
D050091:Dendrimers; D005029:Ethylenediamines; D007202:Indicators and Reagents; D013449:Sulfonamides; D010649:Phenylalanine; D058428:Silica Gel; D012822:Silicon Dioxide; C007305:1,2-dianilinoethane