Synthesis and DNA Cleavage Activity of Artificial Receptor 1,4,7-Triazacyclononane Containing Guanidinoethyl and Hydroxyethyl Side Arms

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• 作者：Xin Sheng ; Xiao-Min Lu ; Jing-Jing Zhang ; Yue-Ting Chen ; Guo-Yuan Lu ; Ying Shao ; Fang Liu ; Qiang Xu
• 刊名：Journal of Organic Chemistry
• 出版年：2007
• 出版时间：March 2, 2007
• 年：2007
• 卷：72
• 期：5
• 页码：1799 - 1802
• 全文大小：198K
• 年卷期：v.72,no.5(March 2, 2007)
• ISSN：1520-6904

文摘

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A novel phosphodiester receptor 1-(2-guanidinoethyl)-4-(2-hydroxyethyl)-1,4,7-triazacyclononane hydrochloride 1 wassynthesized. DNA cleavage efficiency of 1 exhibits remarkable increases compared with its Zn^II complex and corresponding nonguanidinium compound N-(2-hydroxyethyl)-1,4,7-triazacyclononane and parent 1,4,7-triazacyclononane.Kinetic data of DNA cleavage promoted by 1 fit to aMichaelis-Menten-type equation with k_max of 0.160 h^-1giving 10⁷-fold rate acceleration over uncatalyzed DNA. Theacceleration is driven by the spatial proximity of thenucleophilic hydroxyl group and the electrophilic activationfor the phosphodiester by the guanidinium group.