The glycolipid adjuvant α-galactosylceramide (α-GalCer) is known to induce robust T and B cell responses to exogenous antigens through its presentation by CD1d on the surface of antigen presenting cells (APCs). Consequently, α-GalCer, and its related analogues are regarded as excellent immunological adjuvants for use in synthetic vaccines. α-GalCer has previously been utilised as a potent anticancer treatment and has shown therapeutic potential in models of infection, immune mediated toxin protection, autoimmune disorders and inflammatory diseases. More recently, 6’’-modified α-GalCer analogues have shown promise in synthetic vaccines that comprise peptide antigen conjugated to these adjuvants leading to potent immune responses in vivo. Two major synthetic hurdles encountered in the production of 6’’-modified-α-GalCer is selective access to the galactosyl C-6 position and controlling the stereochemical outcome of the glycosylation step. To overcome these, we have developed a new methodology that provides rapid, high yielding, and stereoselective access to a versatile α-GalCer scaffold by utilising a mild borinic acid-mediated glycosylation of 6-functionalised 1,2-anhydro donors. This scaffold provides ready access to 6’’-modified-α-GalCer analogues for vaccine development.

Stereoselective synthesis of 6”-orthogonal α-galactosylceramides for vaccine development

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