title: Tosylated and azidated inulins as key substrates for further chemical modifications to access inulin-based advanced materials: an inulin-based glycocluster.
abstract: We successfully synthesized inulin tosylates by treating commercially available inulin with tosyl chloride and triethylamine in N,N-dimethylacetoamide at the ambient temperature for 24h. The subsequent S(N)2 reactions using sodium azide afford inulin azides that can act as useful substrates for the following Huisgen cycloaddition with alkyne-terminated β-lactoside. The resultant inulin derivative having multiple β-lactosides has excellent affinity towards a β-lactoside binding lectin (RCA(120)). This synthetic strategy has various advantages, such as non-fragmentation of the inulin mainchain and wide applications for various alkyne-terminated functional units. Our strategy can be, therefore, used to develop various inulin derivatives that are applicable for food and medicinal industries.
authors.affiliation: Graduate School of Life Sciences, Toyo University, 1-1-1 Izumino, Itakura-machi, Ora-gun 374-0193, Japan; Bio-Nano Electronics Research Centre, Toyo University, 2100 Kujirai, Kawagoe 350-8585, Japan.
authors.forename: Kazumi
authors.initials: K
authors.lastname: Izawa
authors.forename: Teruaki
authors.initials: T
authors.lastname: Hasegawa
mesh_terms: D001386:Azides / Q000737:chemistry*; D006001:Glycoconjugates / Q000138:chemical synthesis / Q000737:chemistry*; D007444:Inulin / Q000138:chemical synthesis / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy / Q000592:standards; D012015:Reference Standards; D013050:Spectrometry, Fluorescence; D013055:Spectrophotometry, Infrared; D014105:Tosyl Compounds / Q000737:chemistry*
chemical_list: D001386:Azides; D006001:Glycoconjugates; D014105:Tosyl Compounds; D007444:Inulin