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Published on: October 26, 2016
C6-Modifications on chitosan to develop chitosan-based glycopolymers and their lectin-affinities with sigmoidal
Kazuhiro Koshiji1, Yuki Nonaka1, Maho Iwamura2
1Graduate 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.
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.
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