Peer-Reviewed Journal Details
Mandatory Fields
Pilgrim W, O'Reilly C, Murphy PV
2013
September
Molecules (Basel, Switzerland)
Synthesis of α-O- and α-S-glycosphingolipids related to Sphingomonous cell wall antigens using anomerisation.
Published
WOS: 10 ()
Optional Fields
18
9
11198
11218
Analogues of glycolipids from Spingomonadacaece with O- and S- and SO2-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.
10.3390/molecules180911198
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