title: Development of Amylose- and β-Cyclodextrin-Based Chiral Fluorescent Sensors Bearing Terthienyl Pendants.
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-1band 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-1band CyD-1bseems 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-1bprovides not only a fluorescent functionality but also a different chiral recognition site from that of amylose tris(phenylcarbamate).
authors.affiliation: Graduate School of Natural Science and Technology, Kanazawa University, Kakuma-machi, Kanazawa 920-1192, Japan. ikai@se.kanazawa-u.ac.jp.
authors.forename: Tomoyuki
authors.initials: T
authors.lastname: Ikai
authors.affiliation: Graduate School of Natural Science and Technology, Kanazawa University, Kakuma-machi, Kanazawa 920-1192, Japan. robiny87@gmail.com.
authors.forename: Changsik
authors.initials: C
authors.lastname: Yun
authors.affiliation: Graduate School of Natural Science and Technology, Kanazawa University, Kakuma-machi, Kanazawa 920-1192, Japan. y_kojima_1991@yahoo.co.jp.
authors.forename: Yutaka
authors.initials: Y
authors.lastname: Kojima
authors.affiliation: Graduate School of Natural Science and Technology, Kanazawa University, Kakuma-machi, Kanazawa 920-1192, Japan. dsuke3heat@gmail.com.
authors.forename: Daisuke
authors.initials: D
authors.lastname: Suzuki
authors.affiliation: Graduate School of Natural Science and Technology, Kanazawa University, Kakuma-machi, Kanazawa 920-1192, Japan. maeda@se.kanazawa-u.ac.jp.
authors.forename: Katsuhiro
authors.initials: K
authors.lastname: Maeda
authors.affiliation: Graduate School of Natural Science and Technology, Kanazawa University, Kakuma-machi, Kanazawa 920-1192, Japan. kanoh@se.kanazawa-u.ac.jp.
authors.forename: Shigeyoshi
authors.initials: S
authors.lastname: Kanoh
mesh_terms: D000688:Amylose / Q000737:chemistry*; D015374:Biosensing Techniques; D002942:Circular Dichroism; D005456:Fluorescent Dyes / Q000737:chemistry*; D047392:beta-Cyclodextrins / Q000737:chemistry*
chemical_list: D005456:Fluorescent Dyes; D047392:beta-Cyclodextrins; D000688:Amylose
keywords: carbohydrates; chirality; fluorescent sensor; helix; higher-order structure; polysaccharides