Stereoselective synthesis and immunogenic activity of the C-analogue of sulfatide.
[Structure: see text] 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.
Modica
Emilia
E
Dipartimento di Chimica, Biochimica e Biotecnologie per la Medicina, Università di Milano, Via Saldini 50, 20133-Milano, Italy, and Experimental Immunology, Department of Research, Basel University Hospital, Hebelstrasse 20, 4031-Basel, Switzerland.
Compostella
Federica
F
Colombo
Diego
D
Franchini
Laura
L
Cavallari
Marco
M
Mori
Lucia
L
De Libero
Gennaro
G
Panza
Luigi
L
Ronchetti
Fiamma
F
D007371:Interferon-gamma / Q000096:biosynthesis*; D015394:Molecular Structure; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D013433:Sulfoglycosphingolipids / Q000138:chemical synthesis* / Q000276:immunology*
D013433:Sulfoglycosphingolipids; D007371:Interferon-gamma