Trehalose diesters, lipoteichoic acids and α-GalCer: using chemistry to understand immunology

• Glycolipids play an important role in the immune response.
• Trehalose dimycolates, lipoteichoic acids and α-galactosyl ceramide are discussed.
• Synthesis allows for the development of molecular tools.
• Molecular tools allow for valuable insight into biological activity.

It is now widely recognised that glycolipids can play an important role in the activation and modulation of the immune system. Seminal findings in this field included the discovery of ‘endotoxin’ from Gram-negative bacteria, lipoteichoic acids from Gram-positive bacteria and ‘cord factor’ or trehalose dimycolates from mycobacteria. In this mini-review, we present our latest developments on deciphering how glycolipids modulate the immune response through the synthesis and biological evaluation of trehalose glycolipids, lipoteichoic acids and derivatives of α-GalCer. By doing so, we illustrate how chemistry can interface with immunology to aid in the understanding of disease, and show that synthesis can provide a powerful molecular tool for studying the role of glycolipids in biological systems.

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