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Synthesis of a-O- and a-S-Glycosphingolipids Related to Sphingomonous cell Wall Antigens Using Anomerisation
School of Chemistry and Chemical Biology, University College Dublin, Dublin 4, Ireland
School of Chemistry, National University of Ireland Galway, University Road, Galway, Ireland
* Author to whom correspondence should be addressed.
Received: 31 July 2013; in revised form: 4 September 2013 / Accepted: 5 September 2013 / Published: 12 September 2013
Abstract: 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.
Keywords: α-GalCer; anomerisation; glucuronic acid; galacturonic acid; glycoside bond; antigens; NKT cells
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MDPI and ACS Style
Pilgrim, W.; O'Reilly, C.; Murphy, P.V. Synthesis of a-O- and a-S-Glycosphingolipids Related to Sphingomonous cell Wall Antigens Using Anomerisation. Molecules 2013, 18, 11198-11218.
Pilgrim W, O'Reilly C, Murphy PV. Synthesis of a-O- and a-S-Glycosphingolipids Related to Sphingomonous cell Wall Antigens Using Anomerisation. Molecules. 2013; 18(9):11198-11218.
Pilgrim, Wayne; O'Reilly, Ciaran; Murphy, Paul V. 2013. "Synthesis of a-O- and a-S-Glycosphingolipids Related to Sphingomonous cell Wall Antigens Using Anomerisation." Molecules 18, no. 9: 11198-11218.