title: Posttranslationally modified peptides efficiently mimicking neoantigens: a challenge for theragnostics of autoimmune diseases.
abstract: We report the design, synthesis, and immunological evaluation of a series of glycopeptide analogues of the previously described antigenic probe CSF114(Glc), with the aim of understanding the importance of N-glycosylation on Asn residue in multiple sclerosis antibody recognition. The glucopeptide, characterized by a β-turn conformation which is fundamental for a correct presentation of the epitope, has been modified by introducing various natural glycoamino acids in position 7. The new glycopeptides were evaluated by measuring the IgG and IgM antibody titer in multiple sclerosis patients' and normal blood donors' sera. Moreover, we achieved the efficient synthetic strategy of new Asn derivative bearing N-acetylneuraminic acid (Neu5Ac), linked by an N-glycosidic bond, on the side chain of the Asn residue orthogonally protected for Fmoc/tBu SPPS.
authors.affiliation: Laboratory of Peptide and Protein Chemistry and Biology, Polo Scientifico e Tecnologico, University of Florence, Via della Lastruccia 3/13, I-50019 Sesto Fiorentino (FI), Italy.
authors.forename: Francesca
authors.initials: F
authors.lastname: Nuti
authors.forename: Elisa
authors.initials: E
authors.lastname: Peroni
authors.forename: Feliciana
authors.initials: F
authors.lastname: Real-Fernández
authors.forename: M Angeles
authors.initials: MA
authors.lastname: Bonache
authors.forename: Alexandra
authors.initials: A
authors.lastname: Le Chevalier-Isaad
authors.forename: Mario
authors.initials: M
authors.lastname: Chelli
authors.forename: Nadège
authors.initials: N
authors.lastname: Lubin-Germain
authors.forename: Jacques
authors.initials: J
authors.lastname: Uziel
authors.forename: Paolo
authors.initials: P
authors.lastname: Rovero
authors.forename: Francesco
authors.initials: F
authors.lastname: Lolli
authors.forename: Anna Maria
authors.initials: AM
authors.lastname: Papini
mesh_terms: D001324:Autoantigens / Q000737:chemistry* / Q000276:immunology; D006020:Glycopeptides / Q000737:chemistry* / Q000276:immunology; D006801:Humans; D007074:Immunoglobulin G / Q000097:blood* / Q000276:immunology; D007075:Immunoglobulin M / Q000097:blood* / Q000276:immunology; D009103:Multiple Sclerosis / Q000097:blood* / Q000175:diagnosis / Q000276:immunology; D019158:N-Acetylneuraminic Acid / Q000737:chemistry / Q000276:immunology; D011499:Protein Processing, Post-Translational
chemical_list: D001324:Autoantigens; D006020:Glycopeptides; D007074:Immunoglobulin G; D007075:Immunoglobulin M; D019158:N-Acetylneuraminic Acid