کد مقاله | کد نشریه | سال انتشار | مقاله انگلیسی | نسخه تمام متن |
---|---|---|---|---|
1383166 | 1500621 | 2016 | 10 صفحه PDF | دانلود رایگان |
• We synthesized chitosan-based glycopolymers having multiple β-lactosides exclusively at their C6-positions.
• Our synthetic routes started from partially deacetylated chitin.
• Perfect N-deacetylation/phthaloylation and the subsequent C6-selective bromination/azidation afford 6-azide-6-deoxy-N-phthaloyl-chitosan with excellent structural homogeneity.
• The subsequent Cu+-catalyzed Huisgen cycloadditions using alkyne-terminated β-lactoside followed by dephthaloylations gave the chitosan-based glycopolymers.
• We assessed lectin-affinities of the resultant chitosan-based glycopolymers to find their unique sigmoidal binding profiles with lectins.
• We assume that aggregations of the chitosan-based glycopolymers in aqueous media are responsible for the sigmoidal bindings.
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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Journal: Carbohydrate Polymers - Volume 137, 10 February 2016, Pages 277–286