title: Unique tetrameric and hexameric mannoside clusters prepared by click chemistry.
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.
authors.affiliation: Department of Chemistry, Dalhousie University, Halifax, NS B3H 4J3, Canada; Department of Chemistry, Jordan University of Science and Technology, PO Box 3030, Irbid 22110, Jordan. Electronic address: al-mughaid@just.edu.jo.
authors.forename: Hussein
authors.initials: H
authors.lastname: Al-Mughaid
authors.affiliation: Department of Chemistry, Jordan University of Science and Technology, PO Box 3030, Irbid 22110, Jordan.
authors.forename: Raed M
authors.initials: RM
authors.lastname: Al-Zoubi
authors.affiliation: Department of Chemistry, Dalhousie University, Halifax, NS B3H 4J3, Canada.
authors.forename: Nawal K
authors.initials: NK
authors.lastname: Paul
authors.affiliation: Department of Chemistry, Dalhousie University, Halifax, NS B3H 4J3, Canada.
authors.forename: T Bruce
authors.initials: TB
authors.lastname: Grindley
mesh_terms: D000480:Alkynes / Q000737:chemistry; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis*; D001386:Azides / Q000737:chemistry; D002236:Carbohydrate Conformation; D002384:Catalysis; D057930:Click Chemistry / Q000379:methods*; D003300:Copper / Q000737:chemistry*; D061565:Cycloaddition Reaction; D008362:Mannosides / Q000138:chemical synthesis*; D012995:Solubility; D014230:Triazoles / Q000737:chemistry*; D014867:Water
chemical_list: D000480:Alkynes; D000900:Anti-Bacterial Agents; D001386:Azides; D008362:Mannosides; D014230:Triazoles; D014867:Water; D003300:Copper
keywords: Click chemistry; Trizoles; UTIs; α-d-Mannosides