Preparation and application of 3-(methylene-bis(1′,4′-phenylene)dicarbamate-2,3-bis(3,5-dimethylphenylcarbamate)-amylose)-2-hydroxylpropoxy-propylsilyl-appended silica particles as chiral stationary phase for HPLC

Abstract

3-(Methylene-bis(1′,4′-phenylene) dicarbamate-2,3-bis(3,5-dimethylphenylcarbamate)-amylose)-2-hydroxylpropoxy-propylsilyl-appended silica particles (DMP-AM-HPS), a new type of 2, 3-regioselectively substituted amylose-immobilized chiral stationary phase (CSP) for high-performance liquid chromatography (HPLC), have been prepared by treatment of 3-(2,3-dihydroxyl-propoxy)-propylsilyl silica particles with 2,3-bis(3,5-dimethylphenylcarbamate)-amylose and 4,4′-diphenylmethane diisocyanate. The chemical characterization of the bonded particles DMP-AM-HPS has been carried out by elemental analysis and Fourier transform infrared spectroscopic analysis. The chromatographic performance of the DMP-AM-HPS has been evaluated in HPLC under multi-mode conditions including normal phase, reversed phase, and polar organic mobile phase conditions. The DMP-AM-HPS phase has exhibited excellent selectivity in separating enantiomers of a wide range of chiral drug compounds. The result also suggests that unsubstituted C6 hydroxyl groups in the regioselectively substituted amylose not only have important contributions to chiral recognitions and chromatographic separations, but also allow the DMP-AM-HPS to be used as a new type of amylose-immobilized CSP under multi-mode mobile phase conditions in HPLC.

Recent Advances in Separation and Analysis of Chiral Compounds

“…Polysaccharide derivatives are also promising candidates for HPLC CSPs. − A series of amylose derivatives including amylose tris-[(S)-α-methylbenzylcarbamate], 2,3-bis­(3,5-dimethylphenylcarbamate)-amylose, and amylose tris­(3,5-dimethylphenylcarbamate) were covalently bound on silica particles and further packed into a stainless steel column for HPLC separation of α-lipoic acid/α-dihydrolipoic acid, chiral drugs, and nonsteroidal anti-inflammatory drugs, respectively. − Mixed-mode HPLC shows potential in the separation of complex analytes owing to its multiple separation mechanisms. In this regard, a C18 ionic liquid and cellulose cofunctionalized silica packed column was prepared for mixed-mode (reverse-phase/chiral) HPLC separation of hydrophobic and ionic compounds as well as racemates, including warfarin, 1-phenyl-1-propanol, ketoprofen, and styrene oxide, indicating the great potential of cellulose derivative-based multimode CSPs in chiral separation .…”