The C-sulfatide 1b was synthesized through a [2,3]-Wittig sigmatropic rearrangement and a Horner-Wadsworth-Emmons olefination as the key steps. The C-analogue 1b is less immunogenic than natural sulfatide 1a, but induces a preferential secretion of the proinflammatory cytokine IFN-gamma.
Stereoselective synthesis and immunogenic activity of the C-analogue of sulfatide / E. Modica, F. Compostella, D.R. Colombo, L. Franchini, M. Cavallari, L. Mori, G. De Libero, L. Panza, F.C.V. Ronchetti. - In: ORGANIC LETTERS. - ISSN 1523-7060. - 8:15(2006 Jul 20), pp. 3255-3258. [10.1021/ol061100y]
Stereoselective synthesis and immunogenic activity of the C-analogue of sulfatide
E. ModicaPrimo
;F. CompostellaSecondo
;D.R. Colombo;L. Franchini;F.C.V. Ronchetti
2006
Abstract
The C-sulfatide 1b was synthesized through a [2,3]-Wittig sigmatropic rearrangement and a Horner-Wadsworth-Emmons olefination as the key steps. The C-analogue 1b is less immunogenic than natural sulfatide 1a, but induces a preferential secretion of the proinflammatory cytokine IFN-gamma.
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