Stereoselective chemical synthesis of sugar nucleotides via direct displacement of acylated glycosyl bromides.
[structure: see text]. The use of Leloir glycosyltransferases to prepare biologically relevant oligosaccharides and glycoconjugates requires access to sugar nucleoside diphosphates, which are notoriously difficult to efficiently synthesize and purify. We report a novel stereoselective route to UDP- and GDP-alpha-D-mannose as well as UDP- and GDP-beta-L-fucose via direct displacement of acylated glycosyl bromides with nucleoside 5'-diphosphates.
Timmons
Shannon C
SC
Department of Chemistry, Dalhousie University, Halifax, NS, Canada.
Jakeman
David L
DL
D000215:Acylation; D006001:Glycoconjugates / Q000737:chemistry*; D016695:Glycosyltransferases / Q000737:chemistry; D006156:Guanosine Diphosphate Sugars / Q000138:chemical synthesis / Q000737:chemistry; D006842:Hydrocarbons, Brominated / Q000737:chemistry*; D015394:Molecular Structure; D009702:Nucleoside Diphosphate Sugars / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D014539:Uridine Diphosphate Sugars / Q000138:chemical synthesis / Q000737:chemistry
D006001:Glycoconjugates; D006156:Guanosine Diphosphate Sugars; D006842:Hydrocarbons, Brominated; D009702:Nucleoside Diphosphate Sugars; D014539:Uridine Diphosphate Sugars; D016695:Glycosyltransferases