title: Stereoselective synthesis of sugar nucleotides using neighboring group participation.
abstract: A straightforward, efficient method for the chemical synthesis of sugar nucleotides derived from D-mannose and L-fucose precursors is described. This synthetic strategy involves the coupling of acylated glycosyl bromides with nucleoside 5'-diphosphates, which enables the exploitation of neighboring group participation to exclusively prepare diastereomerically pure sugar nucleotides of desired 1,2-trans anomeric configuration. This is the first stereoselective direct coupling approach to sugar nucleotide synthesis. Following deprotection using triethylamine and purification via C18 reversed-phase ion-pair chromatography, UDP- and GDP-alpha-D-mannose as well as UDP- and GDP-beta-L-fucose were obtained in good yield in only four synthetic steps from D-mannose and L-fucose.
authors.affiliation: Dalhousie University, Halifax, Nova Scotia, Canada.
authors.forename: Shannon C
authors.initials: SC
authors.lastname: Timmons
authors.forename: David L
authors.initials: DL
authors.lastname: Jakeman
mesh_terms: D002241:Carbohydrates / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid; D009682:Magnetic Resonance Spectroscopy; D009711:Nucleotides / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: D002241:Carbohydrates; D009711:Nucleotides