A concise synthesis of alpha-sulfatide 1, an analogue of natural glycolipid antigens with potential anti-tumor activity, was performed. Two different approaches to the alpha-glycosidic bond were explored, resulting in a high yield and excellent stereoselectivity. Compound 1 combines the structural features of sulfated beta-GalCer (sulfatide) and alpha-GalCer, which activate specific T cells. alpha-Sulfatide 1 was stimulatory for CD1d-restricted semi-invariant Natural Killer T (iNKT) cell clones, although less potent than alpha-Gal-Cer, while it was not recognized by CD1a-restricted sulfatide-specific T cells.

Synthesis and evaluation of human T cell stimulating activity of an alpha-sulfatide analogue

BARBIERI, LUCIA;COSTANTINO, VALERIA;MANGONI, ALFONSO;
2007

Abstract

A concise synthesis of alpha-sulfatide 1, an analogue of natural glycolipid antigens with potential anti-tumor activity, was performed. Two different approaches to the alpha-glycosidic bond were explored, resulting in a high yield and excellent stereoselectivity. Compound 1 combines the structural features of sulfated beta-GalCer (sulfatide) and alpha-GalCer, which activate specific T cells. alpha-Sulfatide 1 was stimulatory for CD1d-restricted semi-invariant Natural Killer T (iNKT) cell clones, although less potent than alpha-Gal-Cer, while it was not recognized by CD1a-restricted sulfatide-specific T cells.
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11588/102321
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