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

Francesca Nuti; Ilaria Paolini; Francesca Cardona; Mario Chelli; Francesco Lolli; Alberto Brandi; Andrea Goti; Paolo Rovero; Anna M Papini

doi:10.1016/j.bmc.2007.04.007

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

Bioorg Med Chem. 2007 Jun 15;15(12):3965-73. doi: 10.1016/j.bmc.2007.04.007. Epub 2007 Apr 10.

Authors

Francesca Nuti¹, Ilaria Paolini, Francesca Cardona, Mario Chelli, Francesco Lolli, Alberto Brandi, Andrea Goti, Paolo Rovero, Anna M Papini

Affiliation

¹ Laboratory of Peptide & Protein Chemistry & Biology, Polo Scientifico e Tecnologico, University of Florence, I-50019 Sesto Fiorentino (FI), Italy.

PMID: 17459712
DOI: 10.1016/j.bmc.2007.04.007

Abstract

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Asparagine / chemistry*
Autoantibodies / blood
Enzyme-Linked Immunosorbent Assay
Humans
Imino Sugars / chemistry*
Molecular Mimicry*
Multiple Sclerosis / diagnosis
Multiple Sclerosis / immunology
Nuclear Magnetic Resonance, Biomolecular
Peptides / chemistry*
Protein Conformation
Spectrometry, Mass, Electrospray Ionization

Substances

Autoantibodies
Imino Sugars
Peptides
Asparagine