Fmoc-protected iminosugar modified asparagine derivatives as building blocks for glycomimetics-containing peptides.

Research paper by Francesca F Nuti, Ilaria I Paolini, Francesca F Cardona, Mario M Chelli, Francesco F Lolli, Alberto A Brandi, Andrea A Goti, Paolo P Rovero, Anna M AM Papini

Indexed on: 27 Apr '07Published on: 27 Apr '07Published in: Bioorganic & Medicinal Chemistry


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.