title: Development of a fluorescent probe for the study of the sponge-derived simplexide immunological properties.
abstract: Simplexide is a glycolipid of marine origin, endowed with immunological properties, composed of a long chain secondary alcohol glycosylated by an α-d-glucosyl-(1→4)-β-D-galactosyl disaccharide residue. Herein we describe the preparation of a fluorescent derivative of simplexide, labeled at position 6 of the distal glucose with a dansyl group, as a probe for future studies on the mechanism by which simplexide affects the immune system. Fluorescent simplexide was prepared from a 6″-amino functionalized compound, which in turn was obtained through a highly efficient glycosylation between the preformed activated disaccharide and the long chain secondary alcohol 18-pentatriacontanol.
authors.affiliation: Dipartimento di Chimica, Biochimica e Biotecnologie per la Medicina, Università di Milano, Via Saldini 50, 20133 Milano, Italy.
authors.forename: Riccardo
authors.initials: R
authors.lastname: Di Brisco
authors.forename: Fiamma
authors.initials: F
authors.lastname: Ronchetti
authors.forename: Alfonso
authors.initials: A
authors.lastname: Mangoni
authors.forename: Valeria
authors.initials: V
authors.lastname: Costantino
authors.forename: Federica
authors.initials: F
authors.lastname: Compostella
mesh_terms: D000438:Alcohols / Q000737:chemistry; D000818:Animals; D003619:Dansyl Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D004187:Disaccharides / Q000737:chemistry / Q000276:immunology*; D005434:Flow Cytometry; D005456:Fluorescent Dyes / Q000138:chemical synthesis* / Q000737:chemistry; D006017:Glycolipids / Q000737:chemistry* / Q000276:immunology*; D006031:Glycosylation; D007166:Immunosuppressive Agents / Q000737:chemistry*; D047229:Plakortis / Q000737:chemistry*
chemical_list: D000438:Alcohols; D003619:Dansyl Compounds; D004187:Disaccharides; D005456:Fluorescent Dyes; D006017:Glycolipids; D007166:Immunosuppressive Agents