1122631-46-2Relevant academic research and scientific papers
Synthesis of α-O- and α-S-glycosphingolipids related to sphingomonous cell wall antigens using anomerisation
Pilgrim, Wayne,O'Reilly, Ciaran,Murphy, Paul V.
, p. 11198 - 11218 (2013/10/22)
Analogues of glycolipids from Spingomonadacaece with O- and S- and SO 2-linkages have been prepared using chelation induced anomerisation promoted by TiCl4. Included are examples of the anomerisation of intermediates with O- and S-glycosidic linkages as well as isomerisation of β-thioglycuronic acids (β-glycosyl thiols). The β-O-glucuronide and β-O-galacturonide precursors were efficiently prepared using benzoylated trichloroacetimidates. β-Glycosyl thiols were precursors to β-S-derivatives. Triazole containing mimics of the natural glycolipids were prepared using CuI promoted azide-alkyne cycloaddition reactions in THF. The glycolipid antigens are being evaluated currently for their effects on iNKT cells.
α-glycosphingolipids via chelation-induced anomerization of O- And s-glucuronic and galacturonic acid derivatives
Pilgrim, Wayne,Murphy, Paul V.
supporting information; experimental part, p. 939 - 942 (2009/09/08)
Bacterial glycolipids containing either α-glucuronic acid or α-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 α-SO2 glycolipid mimetic, is described from carbohydrate precursors where anomerization is a key step. Very high stereoselectivites (>97:3 in favor of α) were observed from O-glycoside precursors.
