title: Alpha-glycosphingolipids via chelation-induced anomerization of O- and S-glucuronic and galacturonic acid derivatives.
abstract: Bacterial glycolipids containing either alpha-glucuronic acid or alpha-galacturonic acid residues have an important role in the innate-type immune response to gram-negative bacteria. Synthesis of closely related compounds, including a novel alpha-SO(2) glycolipid mimetic, is described from carbohydrate precursors where anomerization is a key step. Very high stereoselectivites (>97:3 in favor of alpha) were observed from O-glycoside precursors.
authors.affiliation: UCD School of Chemistry and Chemical Biology and Centre for Synthesis and Chemical Biology, University College Dublin, Belfield, Dublin 4, Ireland.
authors.forename: Wayne
authors.initials: W
authors.lastname: Pilgrim
authors.forename: Paul V
authors.initials: PV
authors.lastname: Murphy
mesh_terms: D002473:Cell Wall / Q000737:chemistry; D002614:Chelating Agents; D020723:Glucuronic Acid / Q000737:chemistry*; D006028:Glycosphingolipids / Q000138:chemical synthesis* / Q000737:chemistry; D006603:Hexuronic Acids / Q000737:chemistry*; D015394:Molecular Structure; D020578:Sphingomonas / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D002614:Chelating Agents; D006028:Glycosphingolipids; D006603:Hexuronic Acids; C007819:galacturonic acid; D020723:Glucuronic Acid