title: A short synthesis of highly soluble chemoselective chitosan derivatives via "click chemistry".
abstract: A short synthesis of chemoselective chitosan derivatives was achieved by copper-catalyzed Huisgen cycloaddition, which is an ideal reaction for click chemistry, by using N-(4-azidophthaloyl)-chitosan. N-(4-azidophthaloyl)-chitosan was prepared through chemoselective N-bromophthaloylation of chitosan in acidic water and subsequent azidation. The obtained N-(4-bromopthaloyl)-chitosan had higher solubility in common solvents than conventional phthaloyl chitosan. N-(4-azidophthaloyl)-chitosan was successfully converted with ethynyl derivatives having functional groups (hydroxymethyl, phenyl, and methyl ester) in the presence of copper(II) sulfate, sodium ascorbate and/or trimethylamine. FT-IR spectra, elemental analyses, and (1)H and (13)C NMR spectra supported that the desired chitosan derivatives were chemoselectively transferred by these groups with a 1,4-triazole linker.
authors: Department of Chemistry and Biotechnology, Tottori University, Tottori 680-8550, Japan.
authors: Shinsuke
authors: S
authors: Ifuku
authors: Masahiro
authors: M
authors: Wada
authors: Minoru
authors: M
authors: Morimoto
authors: Hiroyuki
authors: H
authors: Saimoto
mesh_terms: D002384:Catalysis / Q000187:drug effects; D002686:Chitin / Q000031:analogs & derivatives / Q000737:chemistry; D048271:Chitosan / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry*; D057930:Click Chemistry / Q000379:methods*; D003300:Copper / Q000494:pharmacology; D003500:Cyclization / Q000187:drug effects; D008954:Models, Biological; D010795:Phthalic Acids / Q000737:chemistry; D012995:Solubility; D017550:Spectroscopy, Fourier Transform Infrared; D013379:Substrate Specificity
chemical_list: D010795:Phthalic Acids; C092806:azidophthalonate; D002686:Chitin; D003300:Copper; D048271:Chitosan