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Published on: July 6, 2012
Unique tetrameric and hexameric mannoside clusters prepared by click chemistry
Hussein Al-Mughaid1, Raed M Al-Zoubi2, Nawal K Paul3
1Department of Chemistry, Dalhousie University, Halifax, NS B3H 4J3, Canada; Department of Chemistry, Jordan University of Science and Technology, PO Box 3030, Irbid 22110, Jordan.
Abstract:
The synthesis of novel tetrameric and hexameric mannoside clusters bearing 1,2,3-trizole linkages via Cu(I)-catalyzed azide-alkyne cycloaddition reaction ("click chemistry") is described. An attractive feature of these multiarmed mannoside clusters as potential inhibitors of uropathogenic Escherichia coli is the use of an aglycone whose length is designed to fit in the tyrosine gate. The acetylated mannosides were deprotected and the corresponding de-O-acetylated mannosides were found to exhibit good water solubility.
