Chemical Synthesis of Mtb Glycolipids; A Tale of Tails

Adriaan J. Minnaard1
1 Stratingh Institute for Chemistry, University of Groningen, Groningen, The Netherlands

The myriad of complex glycolipids found in the Mycobacterium tuberculosis cell wall protects against eradication attempts of the host but, in parallel, elicits immune responses. The latter are heavily studied as the potential bases for a vaccine and target for novel diagnostic markers for the disease.

Access to pure, well defined, glycolipids of known molecular structure strongly facilitates the research in molecular immunology. Chemical synthesis can offer just that. Therefore our group has specialized in the structure elucidation and preparation of mycobacterial glycolipids.

Synthetic strategies have been developed for close to all important glycolipid classes e.g. mycolic acids, sulfoglycolipids, acyl trehaloses, mannose phosphomycoketide, and tuberculosinyl adenosine. Rather than discussing the chemical synthesis in detail, in the presentation it will be explained what characterizes these lipids, what problems are encountered in the structure elucidation and how these compounds can be used in immunological studies.