title: A general and stereoselective route to alpha- or beta-galactosphingolipids via a common four-carbon building block.
abstract: A general synthetic strategy toward alpha- or beta-galactosylceramides and their analogues from 3-azido-2-O-benzyl-1-O-(4-methoxybenzyl)butane-1,2,4-triol is described. The key steps for the installation of the main lipid chain are either a diasteroselective alkynylation reaction yielding the 4R stereocenter of phytosphingosine or a Wittig olefination generating the trans double bond of sphingosine. The methodology allows the preparation of different glycolipids with variations in the structure of the sphingoid base. In particular, three alpha-GalCer-related compounds have been synthesized and evaluated for their ability to activate CD1d-restricted T-cells.
authors.affiliation: Dipartimento di Chimica, Biochimica e Biotecnologie per la Medicina, Università di Milano, Via Saldini 50, 20133-Milano, Italy.
authors.forename: Pamela
authors.initials: P
authors.lastname: Matto
authors.forename: Emilia
authors.initials: E
authors.lastname: Modica
authors.forename: Laura
authors.initials: L
authors.lastname: Franchini
authors.forename: Federica
authors.initials: F
authors.lastname: Facciotti
authors.forename: Lucia
authors.initials: L
authors.lastname: Mori
authors.forename: Gennaro
authors.initials: G
authors.lastname: de Libero
authors.forename: Grazia
authors.initials: G
authors.lastname: Lombardi
authors.forename: Silvia
authors.initials: S
authors.lastname: Fallarini
authors.forename: Luigi
authors.initials: L
authors.lastname: Panza
authors.forename: Federica
authors.initials: F
authors.lastname: Compostella
authors.forename: Fiamma
authors.initials: F
authors.lastname: Ronchetti
mesh_terms: D000276:Adjuvants, Immunologic / Q000138:chemical synthesis / Q000494:pharmacology; D000818:Animals; D005690:Galactose / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D005699:Galactosylceramides / Q000138:chemical synthesis* / Q000494:pharmacology; D008213:Lymphocyte Activation / Q000187:drug effects; D051379:Mice; D013237:Stereoisomerism; D013601:T-Lymphocytes / Q000187:drug effects / Q000276:immunology