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

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

1,2, 1,2 and 2,*
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
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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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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