1006594-40-6Relevant articles and documents
Synthesis of fluorescein-labelled O-mannosylated peptides as components for synthetic vaccines: Comparison of two synthetic strategies
Brimble, Margaret A.,Kowalczyk, Renata,Harris, Paul W. R.,Dunbar, P. Rod,Muir, Victoria J.
, p. 112 - 121 (2008)
Mannose-binding proteins on the surface of antigen-presenting cells (APCs) are capable of recognizing and internalizing foreign agents in the early stages of immune response. These receptors offer a potential target for synthetic vaccines, especially vaccines designed to stimulate T cells. We set out to synthesize a series of fluorescein-labelled O-mannosylated peptides using manual solid phase peptide synthesis (SPPS) on pre-loaded Wang resin, in order to test their ability to bind mannose receptors on human APCs in vitro. A flexible and reliable method for the synthesis of fluorescein-labelled O-mannosylated glycopeptides was desired in order to study their lectin-binding properties using flow cell cytometry. Two synthetic strategies were investigated: incorporation of a fluorescein label into the peptide chain via a lysine side chain ε-amino group at the final stage of standard Fmoc solid phase peptide synthesis or attachment of the fluorescein label to the Nα- amino group of a lysine with further incorporation of a mannosylated peptide unit through the side chain Nε-amino group. The latter strategy proved more effective in that it facilitated SPPS by positioning the growing mannosylated peptide chain further removed from the fluorescein label. The Royal Society of Chemistry 2008.
