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

Molecules

Wayne Pilgrim¹  Ciaran O’Reilly¹ 

[1] School of Chemistry and Chemical Biology, University College Dublin, Dublin 4, Ireland

关键词: α-GalCer;    anomerisation;    glucuronic acid;    galacturonic acid;    glycoside bond;    antigens;    NKT cells;   

DOI  :  10.3390/molecules180911198

来源: mdpi

【 摘 要 】

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.

【 授权许可】

CC BY   
© 2013 by the authors; licensee MDPI, Basel, Switzerland.