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Abstract
Phenylcarbamate derivatives of amylose and β-cyclodextrin show excellent chiral recognition when used as chiral stationary phases (CSPs) for high-performance liquid chromatography. To open up new possibilities of carbohydrate-based materials, we developed chiral fluorescent sensors based on amylose and β-cyclodextrin (Am-1b and CyD-1b, respectively) by attaching fluorescent π-conjugated units on their side chains. Their recognition abilities toward chiral analytes containing a nitrophenyl unit were evaluated by measuring the enantioselective fluorescence quenching behavior. Both sensors showed the same degree of enantioselective fluorescence response for various aromatic nitro compounds. However, in some cases, their enantioselectivities were different depending on the analytes. The difference in the chiral recognition abilities between Am-1b and CyD-1b seems to be based on the structural difference of their inherent backbones, that is, the one-handed helical structure and cyclic structure, respectively. The study on the resolution ability of the Am-1b-based CSP revealed that the terthienyl-based pendant of Am-1b provides not only a fluorescent functionality but also a different chiral recognition site from that of amylose tris(phenylcarbamate).
Highlights
Interesting chiral molecules are ubiquitous in the fields of drugs, agrochemicals, food additives and fragrances
Natural polysaccharides hardly show marked chiral discrimination ability [5,6], their appropriately modified derivatives are known to show excellent chiral recognition for a wide variety of racemic compounds when applied to chiral stationary phases (CSPs) for high-performance liquid chromatography (HPLC) [7,8,9,10]
We developed a novel amylose-based chiral fluorescent sensor
Summary
Interesting chiral molecules are ubiquitous in the fields of drugs, agrochemicals, food additives and fragrances. It has been widely recognized that the physiological properties of two enantiomers are often different owing to the sophisticated chiral discrimination ability of enzymes and receptors in the body [1,2,3,4]. To eliminate the incorrect use of hazardous isomers that may have undesired properties, chiral discrimination has been viewed as an important issue, in the pharmaceutical industries. Polysaccharides, such as amylose and cellulose, are renewable and abundant resources that are optically active. Great success has been achieved in the application of polysaccharide derivatives in CSP materials, their application in other fields of chiral materials has been highly restricted. A cellulose-based chiral fluorescent sensor forin asymmetric [11,12]
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