title: Synthesis and antioxidant property of novel 1,2,3-triazole-linked starch derivatives via 'click chemistry'.
abstract: Based on the copper (I) catalyzed Huisgen azide-alkyne cycloaddition (click chemistry), the novel synthesis of a variety of 1,2,3-triazole-linked starch derivatives was developed, including 6-hydroxymethyltriazole-6-deoxy starch (HMTST), 6-hydroxyethyltriazole-6-deoxy starch (HETST), 6-hydroxypropyltriazole-6-deoxy starch (HPTST), and 6-hydroxybutyltriazole-6-deoxy starch (HBTST). Their antioxidant properties against hydroxyl-radical, DPPH-radical, and superoxide-radical were evaluated in vitro, respectively. The antioxidant activity of the obtained novel amphiprotic starch derivatives via 'click reaction' exhibited remarkable improvement over starch. And the scavenging effect indices of most of the products were higher than 60% at 1.6 mg/mL against hydroxyl-radical and DPPH-radical. Moreover, the scavenging effect of the products against superoxide-radical attained 90% above at 0.1mg/mL. Generally, the antioxidant activity decreased in the order: HBTST>HPTST>HETST>HMTST>starch. Furthermore, the order of their antioxidant activity was consistent with the electron-donating ability of different substituted groups of the 1,2,3-triazoles. The substituted groups with stronger electron supplying capacity provided more electrons to the various radicals, which relatively enhanced the capacity for scavenging free radicals.
authors.affiliation: Key Laboratory of Coastal Biology and Bioresource Utilization, Yantai Institute of Coastal Zone Research, Chinese Academy of Sciences, Yantai 264003, China; University of Chinese Academy of Sciences, Beijing 100049, China.
authors.forename: Wenqiang
authors.initials: W
authors.lastname: Tan
authors.affiliation: Key Laboratory of Coastal Biology and Bioresource Utilization, Yantai Institute of Coastal Zone Research, Chinese Academy of Sciences, Yantai 264003, China.
authors.forename: Qing
authors.initials: Q
authors.lastname: Li
authors.affiliation: Key Laboratory of Coastal Biology and Bioresource Utilization, Yantai Institute of Coastal Zone Research, Chinese Academy of Sciences, Yantai 264003, China; University of Chinese Academy of Sciences, Beijing 100049, China.
authors.forename: Wancong
authors.initials: W
authors.lastname: Li
authors.affiliation: Key Laboratory of Coastal Biology and Bioresource Utilization, Yantai Institute of Coastal Zone Research, Chinese Academy of Sciences, Yantai 264003, China.
authors.forename: Fang
authors.initials: F
authors.lastname: Dong
authors.affiliation: Key Laboratory of Coastal Biology and Bioresource Utilization, Yantai Institute of Coastal Zone Research, Chinese Academy of Sciences, Yantai 264003, China. Electronic address: zhanyongguo@hotmail.com.
authors.forename: Zhanyong
authors.initials: Z
authors.lastname: Guo
mesh_terms: D000975:Antioxidants / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D057930:Click Chemistry; D016166:Free Radical Scavengers / Q000737:chemistry / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D012995:Solubility; D017550:Spectroscopy, Fourier Transform Infrared; D013213:Starch / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D014230:Triazoles / Q000737:chemistry*
chemical_list: D000975:Antioxidants; D016166:Free Radical Scavengers; D014230:Triazoles; D013213:Starch
keywords: Antioxidant activity; Click chemistry; Starch derivatives