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Molecules 2013, 18(9), 11198-11218; doi:10.3390/molecules180911198

Synthesis of a-O- and a-S-Glycosphingolipids Related to Sphingomonous cell Wall Antigens Using Anomerisation

1
School of Chemistry and Chemical Biology, University College Dublin, Dublin 4, Ireland
2
School of Chemistry, National University of Ireland Galway, University Road, Galway, Ireland
*
Author to whom correspondence should be addressed.
Received: 31 July 2013 / Revised: 4 September 2013 / Accepted: 5 September 2013 / Published: 12 September 2013
(This article belongs to the Special Issue Synthesis, Structure, Analysis and Properties of Glycolipids)
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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 α-GalCer; anomerisation; glucuronic acid; galacturonic acid; glycoside bond; antigens; NKT cells
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This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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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.

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