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New chitosan derivatives bearing guanidinium functions were synthesized following different synthesis strategies. N-guanidinium chitosan acetate and N-guanidinium chitosan chloride were synthesized by direct reaction between chitosan and cyanamide in the presence of scandium(III) triflate. The synthesis of N-guanidinium chitosan (N,N′-dicyclohexyl) chloride and N-guanidinium chitosan (N-(3-dimethylaminopropyl)-N'-ethyl hydrochloride) chloride involved the reaction of chitosan with carbodiimides in ionic liquid. The chitosan derivatives were characterized by analytical techniques including ¹³C solid state NMR, FT-IR spectroscopies, thermogravimetry and elemental analysis. The antimicrobial properties of chitosan and the new derivatives were investigated using the minimal inhibitory concentration (MIC) technique. All new guanylated chitosan derivatives displayed high antimicrobial activity in comparison …