title: C6-Modifications on chitosan to develop chitosan-based glycopolymers and their lectin-affinities with sigmoidal binding profiles.
abstract: Chitosan-based glycopolymers having multiple β-lactosides exclusively at their C6-positions were successfully synthesized from partially deacetylated chitin through perfect N-deacetylation/phthaloylation and C6-selective bromination/azidation to afford 6-azide-6-deoxy-N-phthaloyl-chitosan and the subsequent Cu(+)-catalyzed Huisgen cycloadditions using alkyne-terminated β-lactoside and/or quaternary ammonium modules followed by dephthaloylations. Lectin-affinities of the resultant chitosan-based glycopolymers were assessed through fluorescence titration assays to show their unique sigmoidal binding profiles with amplified binding constants.
authors.affiliation: Graduate School of Life Sciences, Toyo University, 1-1-1 Izumino, Itakura-machi, Ora-gun 374-0193, Gunma, Japan; Bio-Nano Electronics Research Centre, Toyo University, 2100 Kujirai, Kawagoe 350-8585, Saitama, Japan.
authors.forename: Kazuhiro
authors.initials: K
authors.lastname: Koshiji
authors.affiliation: Graduate School of Life Sciences, Toyo University, 1-1-1 Izumino, Itakura-machi, Ora-gun 374-0193, Gunma, Japan; Bio-Nano Electronics Research Centre, Toyo University, 2100 Kujirai, Kawagoe 350-8585, Saitama, Japan.
authors.forename: Yuki
authors.initials: Y
authors.lastname: Nonaka
authors.affiliation: Department of Life Sciences, Toyo University, 1-1-1 Izumino, Itakura-machi, Ora-gun 374-0193, Gunma, Japan.
authors.forename: Maho
authors.initials: M
authors.lastname: Iwamura
authors.affiliation: Department of Life Sciences, Toyo University, 1-1-1 Izumino, Itakura-machi, Ora-gun 374-0193, Gunma, Japan.
authors.forename: Fumiko
authors.initials: F
authors.lastname: Dai
authors.affiliation: Department of Life Sciences, Toyo University, 1-1-1 Izumino, Itakura-machi, Ora-gun 374-0193, Gunma, Japan.
authors.forename: Ryoji
authors.initials: R
authors.lastname: Matsuoka
authors.affiliation: Bio-Nano Electronics Research Centre, Toyo University, 2100 Kujirai, Kawagoe 350-8585, Saitama, Japan; Department of Life Sciences, Toyo University, 1-1-1 Izumino, Itakura-machi, Ora-gun 374-0193, Gunma, Japan. Electronic address: t-hasegawa@toyo.jp.
authors.forename: Teruaki
authors.initials: T
authors.lastname: Hasegawa
mesh_terms: D048271:Chitosan / Q000737:chemistry*; D057930:Click Chemistry; D037102:Lectins / Q000737:chemistry*; D011108:Polymers / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D037102:Lectins; D011108:Polymers; D048271:Chitosan
keywords: Chitosan; Click chemistry; Glycopolymer; Huisgen cycloaddition; Regioselective modifications