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 / L., Franchini; P., Matto; F., Ronchetti; L., Panza; Barbieri, Lucia; Costantino, Valeria; Mangoni, Alfonso; M., Cavallari; L., Morid; G., DE LIBERO. - In: BIOORGANIC & MEDICINAL CHEMISTRY. - ISSN 1464-3391. - STAMPA. - 15:(2007), pp. 5529-5536. [10.1016/j.bmc.2007.05.044]
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.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
