Controlled Immobilization of Polysaccharide Derivatives for Efficient Chiral Separation

Abstract

Polysaccharide‐based chiral packing materials (CPMs) for high‐performance liquid chromatography (HPLC) have been widely used to determine the enantiomeric excess of a wide range of chiral compounds and also to resolve them on an industrial scale. These CPMs have conventionally been prepared by physically coating a chromatographic support with the polysaccharide derivatives. However, solvents that swell or dissolve the polysaccharide derivatives cannot be used as an eluent component because the column performance will be drastically decreased. This restriction on eluent selection is sometimes a serious issue for efficient analytical and preparative enantioseparations. In order to enhance the diversity of the eluent selection, immobilized CPMs, in which the polysaccharide derivatives are immobilized onto chromatographic supports, have been developed since 1987. This review summarizes the various immobilization methods of the polysaccharide derivatives mainly onto silica gel as a chromatographic support.

Synthesis and chiral recognition of helical poly(phenylacetylene)s bearing l‐phenylglycinol and its phenylcarbamates as pendants

“…One of the key points of this separation technique is to design and prepare the efficient chiral stationary phases (CSPs) with high chiral recognition abilities. Although polysaccharide derivatives, especially the phenylcarbamates and benzoates of cellulose and amylose with high chiral recognition abilities have been developed as the popular CSPs for a wide range of chiral compounds, various optically active synthetic polymers with a controllable helical sense have also been applied as the CSPs for the HPLC separation of enantiomers in the last two decades . Among the synthetic polymers, the helical poly(phenylacetylene) derivatives bearing chiral pendants have been proved to be good candidates as novel CSPs for the HPLC separation of enantiomers due to their helical structures induced by chiral pendants .…”

Hybrid monolithic columns coated with cellulose tris(3,5-dimethylphenyl-carbamate) for enantioseparations in capillary electrochromatography and capillary liquid chromatography

“…Polysaccharide derivatives have occupied a unique place among these chiral stationary phases (CSPs) and have been the most widely used chiral selector for enantioseparation of a broad range of chiral compounds [21][22][23][24]. Several kinds of polysaccharide derivatives such as cellulose tris(3,5-dimethylphenylcarbamate) (CDMPC), cellulose tris(4-methylbenzoate), cellulose tris(3,5-dichlorophenyl carbamate) and amylose tris(3,5-dimethylphenylcarbamate) have been coated or immobilized onto the silica-based monoliths and successfully applied for enantioseparations in CLC or CEC [25,26,27,28,29].…”

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

“…Similar interactions between analytes and chiral selectors are easily formed, thus leading to their enantioseparation. Second, as compared to the coated cellulose CSP, chemically bonded linkages between chiral selectors and silica gel may lead to some changes of cellulose's spatial structure, further showing different enantioseparation abilities .…”