title: Synthesis of bivalent glycoclusters containing GlcNAc as hexasaccharide mimetics. Bactericidal activity against Helicobacter pylori.
abstract: The Cu(I) catalysed cycloaddition reaction of azides and alkynes has been used to generate a series of divalent GlcNAc clusters with both α and β configurations. These glycoclusters can be considered as potential mimetics of an anti Helicobacter pylori hexasaccharide as they present two GlcNAc residues grafted onto a core scaffold. Two bivalent compounds based on α-O-GlcNAc were identified that selectively reduced the viability of H. pylori. These compounds showed activity towards different strains of H. pylori (Pu4 vs P12). The activity of the oligosaccharide mimetics is speculated to be due to the GlcNAc residues being able to adopt spatial arrangements accessible to the anti H. pylori hexasaccharide which may be important for activity.
authors.affiliation: School of Chemistry, National University of Ireland Galway, University Road, Galway, Ireland.
authors.forename: Dandan
authors.initials: D
authors.lastname: Yan
authors.forename: Julie
authors.initials: J
authors.lastname: Naughton
authors.forename: Marguerite
authors.initials: M
authors.lastname: Clyne
authors.forename: Paul V
authors.initials: PV
authors.lastname: Murphy
mesh_terms: D000117:Acetylglucosamine / Q000737:chemistry*; D000480:Alkynes / Q000737:chemistry; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D001386:Azides / Q000737:chemistry; D040761:Biomimetic Materials / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D002236:Carbohydrate Conformation; D002384:Catalysis; D003300:Copper / Q000737:chemistry; D006001:Glycoconjugates / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D016480:Helicobacter pylori / Q000187:drug effects*; D008826:Microbial Sensitivity Tests; D008958:Models, Molecular; D009844:Oligosaccharides / Q000737:chemistry*; D013329:Structure-Activity Relationship
chemical_list: D000480:Alkynes; D000900:Anti-Bacterial Agents; D001386:Azides; D006001:Glycoconjugates; D009844:Oligosaccharides; D003300:Copper; D000117:Acetylglucosamine