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Issue 1, 2008
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Synthesis of fluorescein-labelled O-mannosylated peptides as components for synthetic vaccines: comparison of two synthetic strategies

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Abstract

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.

Graphical abstract: Synthesis of fluorescein-labelled O-mannosylated peptides as components for synthetic vaccines: comparison of two synthetic strategies

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Publication details

The article was received on 22 Aug 2007, accepted on 05 Oct 2007 and first published on 26 Oct 2007


Article type: Paper
DOI: 10.1039/B712926B
Citation: Org. Biomol. Chem., 2008,6, 112-121
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    Synthesis of fluorescein-labelled O-mannosylated peptides as components for synthetic vaccines: comparison of two synthetic strategies

    M. A. Brimble, R. Kowalczyk, P. W. R. Harris, P. R. Dunbar and V. J. Muir, Org. Biomol. Chem., 2008, 6, 112
    DOI: 10.1039/B712926B

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