Abstract
The development of chiral stationary phases (CSPs) for liquid chromatography (LC) revolutionized the enantioseparation and, nowadays, different types of CSPs are commercially available. Polysaccharide-based CSPs are one of the most versatile and widely used for both analytical and preparative applications and they are able to resolve several classes of racemates. Phenylcarbamates of amylose and cellulose derivatives are the most successful; however, polysaccharide-based CSPs comprising marine-derived polysaccharides are also described revealing high chiral recognition abilities and wider range of mobile phases. A literature survey covering the report on chitin and chitosan based CSPs is presented. The chemical structure of the chiral selectors, their development and applications in chiral LC are emphasized.
Highlights
Nowadays, there are several types of chiral stationary phases (CSPs), including Pirkle-type, ligand-exchange-type, crown ether-based, cyclodextrin-based, macrocyclic antibiotics-based, ion-exchange-type, polysaccharide-based, molecular imprinted, synthetic polymer-based, proteinbased, among others [1,2,3,4].Polysaccharides are polymers comprising several units of monosaccharides linked to each other by a glycosidic bond [5]
The first study reporting the use of polysaccharide derivatives as a practical chiral packing material for liquid chromatography (LC) columns was described by Hesse and Hagel in 1973 [6]
Among the developed amylose and cellulose trisThe carbamate derivatives of amylose and cellulose can be synthesized by reaction of the phenylcarbamates, the 3,5-dimethylphenyl derivatives proved to have the best enantiorecognition polysaccharide with the corresponding isocyanate comprising the moiety of the desired derivative performance [8,9,43,44] being, nowadays, the most widely used CSPs (Figure 2)
Summary
There are several types of chiral stationary phases (CSPs), including Pirkle-type, ligand-exchange-type, crown ether-based, cyclodextrin-based, macrocyclic antibiotics-based, ion-exchange-type, polysaccharide-based, molecular imprinted, synthetic polymer-based, proteinbased, among others [1,2,3,4]. Phenylcarbamates are the derivatives most studied due to their high chiral ability recognition and the possibility to explore different aryl substituents [35,36,37,38,39,40,41]. Phenylcarbamates are the derivatives most studied Figure due to2.their high chiral ability3,5-dimethylphenylcarbamate recognition and the possibility explore different. Among the developed amylose and cellulose trisThe carbamate derivatives of amylose and cellulose can be synthesized by reaction of the phenylcarbamates, the 3,5-dimethylphenyl derivatives proved to have the best enantiorecognition polysaccharide with the corresponding isocyanate comprising the moiety of the desired derivative performance [8,9,43,44] being, nowadays, the most widely used CSPs (Figure 2). Their lower chiral recognition ability is the main disadvantage, which can be explained by the fact that the immobilization of the polysaccharide derivative on the chromatographic support is done through the hydroxyl groups, causing a disturbance in the high-ordered structures of the polysaccharide [27]
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