Synthesis of an O-alkynyl-chitosan and its chemoselective conjugation with a PEG-like amino-azide through click chemistry
authors Oliveira, JR; Martins, MCL; Mafra, L; Comes, P
nationality International
journal CARBOHYDRATE POLYMERS
author keywords Azide-alkyne coupling; Bioadhesion; Biomaterials; Chitosan click chemistry; FTIR; Huisgen's 1,3-dipolar cycloaddition; Size-exclusion chromatography; Solid-state NMR; XPS
keywords BIOMEDICAL APPLICATIONS; CHEMICAL-MODIFICATIONS; DRUG-DELIVERY; FT-IR; NANOPARTICLES; CHITIN; ACETYLATION; DERIVATIVES; COPOLYMERS; HYDROGELS
abstract N-Phthaloyl-chitosan O-prop-2-ynyl carbamate was prepared as a biopolymer amenable to undergo chemoselective conjugation by azide-alkyne coupling, while allowing upturn of chitosan's amines after dephthaloylation. N-phthaloylchitosan was prepared according to previously described methods and, due to its low solubility in current organic media, subsequent modifications were run in heterogeneous conditions. Activation of hydroxyls with carbonyl-1,1 '-diimidazole and coupling to propargylamine yielded N-phthaloyl-chitosan O-prop-2-ynyl carbamate, then coupled to a model PEG-like azide by azide-alkyne coupling, giving the expected triazolyl conjugate. N-Dephthaloylation allowed recovery of the free amines, responsible for chitosan's bioadhesion and tissue-regeneration properties. The structures of all polymers were confirmed by Fourier-transformed infra-red (FT-IR) and X-ray photoelectron (XPS) spectroscopies, as well as by solid-state nuclear magnetic resonance (SSNMR). All chitosan derivatives were poorly soluble in both aqueous and organic media, which makes them suitable for topical applications or for removal of toxic substances from either the gastric intestinal tract or environmental sources. (C) 2011 Elsevier Ltd. All rights reserved.
publisher ELSEVIER SCI LTD
issn 0144-8617
year published 2012
volume 87
issue 1
beginning page 240
ending page 249
digital object identifier (doi) 10.1016/j.carbpol.2011.07.043
web of science category Chemistry, Applied; Chemistry, Organic; Polymer Science
subject category Chemistry; Polymer Science
unique article identifier WOS:000297389000032
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journal impact factor 5.158
5 year journal impact factor 5.326
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