title: Toward analogues of MraY natural inhibitors: synthesis of 5'-triazole-substituted-aminoribosyl uridines through a Cu-catalyzed azide-alkyne cycloaddition.
abstract: A straightforward strategy for the synthesis of triazole-containing MraY inhibitors has been developed. It involves the sequential introduction of a terminal alkyne at the 5' position of an uridine derivative and O-glycosylation with a protected aminoribose leading to an elaborated alkyne scaffold. An efficient Cu(I)-catalyzed azide-alkyne cycloaddition (CuAAC) allowed the introduction of chemical diversity toward a small library of inhibitors.
authors.affiliation: Laboratoire de Chimie et Biochimie Pharmacologiques et Toxicologiques, Université Paris Descartes , UMR 8601 CNRS, 45 rue des Saints Pères, 75006 Paris, France.
authors.forename: Mickaël J
authors.initials: MJ
authors.lastname: Fer
authors.forename: Samir
authors.initials: S
authors.lastname: Olatunji
authors.forename: Ahmed
authors.initials: A
authors.lastname: Bouhss
authors.forename: Sandrine
authors.initials: S
authors.lastname: Calvet-Vitale
authors.forename: Christine
authors.initials: C
authors.lastname: Gravier-Pelletier
mesh_terms: D000480:Alkynes / Q000737:chemistry; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry; D001386:Azides / Q000737:chemistry; D001426:Bacterial Proteins / Q000037:antagonists & inhibitors* / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D061565:Cycloaddition Reaction; D024881:Drug Resistance, Bacterial; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry; D006031:Glycosylation; D014166:Transferases / Q000037:antagonists & inhibitors* / Q000737:chemistry*; D017855:Transferases (Other Substituted Phosphate Groups); D014230:Triazoles / Q000138:chemical synthesis* / Q000737:chemistry; D014529:Uridine / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000480:Alkynes; D000900:Anti-Bacterial Agents; D001386:Azides; D001426:Bacterial Proteins; D004791:Enzyme Inhibitors; D014230:Triazoles; D003300:Copper; D014166:Transferases; D017855:Transferases (Other Substituted Phosphate Groups); C079803:mraY protein, Bacteria; D014529:Uridine