Chemoenzymatic Synthesis of Arabinomannane (AM) Glycoconjugates as Potential Vaccines for Tuberculosis

    • Zhihao Lia
    • Teodora Bavarob
    • Sara Tengattinib
    • Roberta Bernardinic
    • Maurizio Matteic,d
    • Francesca Annunziatae
    • Richard B. Colea
    • Changping Zhenga
    • Matthieu Sollogouba
    • Lucia Tamborinie
    • Marco Terrenib
    • Yongmin Zhanga
    • aSorbonne Université, CNRS, Institut Parisien de Chimie Moléculaire, UMR 8232, 4 Place Jussieu, 75005 Paris, France.
    • bDrug Sciences Department, University of Pavia, Viale Taramelli 12, 27100 Pavia, Italy.
    • cItaly Centro Servizi Interdipartimentale – STA, University of Rome “Tor Vergata”, Rome, Italy.
    • dDept. of Biology, University of Rome “Tor Vergata”, Rome, Italy.
    • eDepartment of Pharmaceutical Sciences, University of Milan, via Mangiagalli 25, 20133 Milan, Italy.

    Mycobacteria infection resulting in tuberculosis (TB) is one of the top ten leading causes of death worldwide in 2018, and lipoarabinomannan (LAM) has been confirmed to be the most important antigenic oligosaccharide on the TB cell surface. In this study, a convenient synthetic method has been developed for synthesizing three branched oligosaccharides derived from LAM, in which a core building block was prepared by enzymatic hydrolysis in flow chemistry with excellent yield. After a series of steps of glycosylations, the obtained oligosaccharides were conjugated with recombinant human serum albumin (rHSA) and the ex-vivo ELISA tests were performed using serum obtained from several TB-infected patients, in order to evaluate the affinity of the glycoconjugate products for the human LAM-antibodies. The evaluation results are positive, especially compound 21 that exhibited excellent activity which could be considered as a lead compound for the future development of a new glycoconjugated vaccine against TB.

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