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. 2014 Aug 21;12(8):4635–4658. doi: 10.3390/md12084635

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© 2014 by the authors; licensee MDPI, Basel, Switzerland.

This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/).

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Scheme 1 — Synthesis of final N-(2-(N,N,N-trimethylammoniumyl)acetyl)-chitosan chloride (TMA-CS) (6ⁱ^–v) and N-(2-(1-pyridiniumyl)acetyl)-chitosan chloride (PyA-CS)(8ⁱ^–v) derivatives. Reactions and conditions: (a) MeSO₃H/H₂O (1:1), 10 °C, 1 h (90%); (b) tert-butyl-dimethylsilyl chloride (TBDMSCl), imidazole, DMSO, 25 °C, 24 h (96%); (c) bromoacetyl bromide, Et₃N, CH₂Cl₂, −20 °C, 1 h (92%); (d) Me₃N (31%–35% wt in EtOH, 4.2 M),_CH₂Cl₂,_25 °C, 12 h; (e) pyridine, 25 °C, 24 h; (f) conc HCl/MeOH, 25 °C, 24 h, ion exchanged by (8%) acqueos NaCl (w/v), 1 h, dialysed against de-ionised water, 48h.