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-GalCer, 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, L. BARBIERI, V. COSTANTINO, A. MANGONI, M. CAVALLARI, L. MORI, G. DE LIBERO. - In: BIOORGANIC & MEDICINAL CHEMISTRY. - ISSN 0968-0896. - 15:16(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
L. FranchiniPrimo
;P. MattoSecondo
;F. Ronchetti;
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-GalCer, while it was not recognized by CD1a-restricted sulfatide-specific T cells.Pubblicazioni consigliate
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