Sialic acid and sialyl-lactose glyco-conjugates: Design, synthesis and binding assays to lectins and swine influenza H1N1 virus

Stella Zevgiti, Juliana Gonzalez Zabala, Ayub Darji, Ursula Dietrich, Eugenia Panou-Pomonis, Maria Sakarellos-Daitsiotis

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    14 Citations (Scopus)

    Abstract

    The terminal parts of the influenza hemagglutinin (HA) receptors α2,6- and α2,3-sialyllactoses were conjugated to an artificial carrier, named sequential oligopeptide carrier (SOC 4), to formulate human and avian receptor mimics, respectively. SOC 4, formed by the tripeptide unit Lys-Aib-Gly, adopts a rigid helicoids-type conformation, which enables the conjugation of biomolecules to the Lys-N εH 2 groups. By doing so, it preserves their initial conformations and functionalities of the epitopes. We report that SOC 4-glyco-conjugate bearing two copies of the α2,6-sialyllactose is specifically recognized by the biotinylated Sambucus nigra (elderberry) bark lectin, which binds preferentially to sialic acid in an α2,6-linkage. SOC 4-glyco-conjugate bearing two copies of the α2,3-sialyllactose was not recognized by the biotinylated Maackia amurensis lectin, despite its well-known α2,3-sialyl bond specificity. However, preliminary immune blot assays showed that H1N1 virus binds to both the SOC 4-glyco-conjugates immobilized onto nitrocellulose membrane. It is concluded that Ac-SOC 4[(Ac) 2,(3'SL-Aoa) 2]-NH 2 5 and Ac-SOC 4[(Ac) 2,(6'SL-Aoa) 2]-NH 2 6 mimic the HA receptors. These findings could be useful for easy screening of binding and inhibition assays of virus-receptor interactions. © 2011 European Peptide Society and John Wiley & Sons, Ltd.
    Original languageEnglish
    Pages (from-to)52-58
    JournalJournal of Peptide Science
    Volume18
    Issue number1
    DOIs
    Publication statusPublished - 1 Jan 2012

    Keywords

    • Chemoselective oxime ligation
    • HA-binding receptor mimics
    • Immune blot binding of H1N1
    • Influenza virus
    • Lectin binding assays
    • Sequential oligopeptide carrier (SOC ) 4
    • SOC -sialo-conjugates 4

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