Synthesis of a fluorescent ganglioside GM1 derivative and screening of a synthetic peptide library for GM1 binding sequence motifs

Niels Röckendorf, Steffen Bade, Timothy R. Hirst, Hans H. Gorris, Andreas Frey*

*Corresponding author for this work

    Research output: Contribution to journalArticlepeer-review

    12 Citations (Scopus)

    Abstract

    A ganglioside GM1 probe bearing a dark-red fluorescent dye at the sphingosine moiety of the molecule was prepared by a convenient one-pot synthesis. The labeled GM1 permitted the detection of the natural ganglioside GM1 ligand Escherichia coli heat-labile enterotoxin subunit B (EtxB) in picomole quantities on a solid support. When an epitope mapping of several ganglioside binding proteins and protein fragments was performed by screening a cellulose membrane-bound synthetic library of 64 16mer peptides with the new probe, several peptides displaying ganglioside G M1 affinity could be identified. We consider the labeled glycolipid described herein a versatile tool for manifold biochemical investigations.

    Original languageEnglish
    Pages (from-to)573-578
    Number of pages6
    JournalBioconjugate Chemistry
    Volume18
    Issue number2
    DOIs
    Publication statusPublished - 2007

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