title: Stereoselective synthesis and immunogenic activity of the C-analogue of sulfatide.
abstract: [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.
authors.affiliation: 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.
authors.forename: Emilia
authors.initials: E
authors.lastname: Modica
authors.forename: Federica
authors.initials: F
authors.lastname: Compostella
authors.forename: Diego
authors.initials: D
authors.lastname: Colombo
authors.forename: Laura
authors.initials: L
authors.lastname: Franchini
authors.forename: Marco
authors.initials: M
authors.lastname: Cavallari
authors.forename: Lucia
authors.initials: L
authors.lastname: Mori
authors.forename: Gennaro
authors.initials: G
authors.lastname: De Libero
authors.forename: Luigi
authors.initials: L
authors.lastname: Panza
authors.forename: Fiamma
authors.initials: F
authors.lastname: Ronchetti
mesh_terms: D007371:Interferon-gamma / Q000096:biosynthesis*; D015394:Molecular Structure; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D013433:Sulfoglycosphingolipids / Q000138:chemical synthesis* / Q000276:immunology*
chemical_list: D013433:Sulfoglycosphingolipids; D007371:Interferon-gamma