Fmoc-protected iminosugar modified asparagine derivatives as building blocks for glycomimetics-containing peptides.
CSF114(Glc) is the first synthetic Multiple Sclerosis Antigenic Probe able to identify autoantibodies in a statistically significant number of Multiple Sclerosis patients. The beta-turn conformation of this glucopeptide is fundamental for a correct presentation of the epitope Asn(Glc). To verify the influence of sugar mimics in antibody recognition in Multiple Sclerosis, we synthesized Fmoc-protected Asn derivatives containing alkaloid-type sugar mimics. The corresponding glycomimetics-containing peptide derivatives of the CSF114-type sequence were tested in competitive and solid-phase non-competitive ELISA on Multiple Sclerosis patients' sera.
Nuti
Francesca
F
Laboratory of Peptide & Protein Chemistry & Biology, Polo Scientifico e Tecnologico, University of Florence, I-50019 Sesto Fiorentino (FI), Italy.
Paolini
Ilaria
I
Cardona
Francesca
F
Chelli
Mario
M
Lolli
Francesco
F
Brandi
Alberto
A
Goti
Andrea
A
Rovero
Paolo
P
Papini
Anna M
AM
D001216:Asparagine / Q000737:chemistry*; D001323:Autoantibodies / Q000097:blood; D004797:Enzyme-Linked Immunosorbent Assay; D006801:Humans; D050111:Imino Sugars / Q000737:chemistry*; D018716:Molecular Mimicry; D009103:Multiple Sclerosis / Q000175:diagnosis / Q000276:immunology; D019906:Nuclear Magnetic Resonance, Biomolecular; D010455:Peptides / Q000737:chemistry*; D011487:Protein Conformation; D021241:Spectrometry, Mass, Electrospray Ionization
D001323:Autoantibodies; D050111:Imino Sugars; D010455:Peptides; D001216:Asparagine