Chemical Synthesis of Marine-Derived Sulfoglycolipids, a New Class of Molecular Adjuvants.

Vaccines play a primary role in the protection of human health by preventing infectious and chronic diseases. Recently we have reported 1,2--distearoyl-3--β-d-sulfoquinovosylglycerol (β-SQDG18), here named Sulfavant A (), which shows promising properties as a new molecular adjuvant in in vitro and in vivo tests. In the present manuscript, we provide full details about a synthetic strategy for the preparation of , including a discussion of chemical determinants of the activity and the major technical hurdles we faced during the study. Synthesis of Sulfavant A () is achieved by a versatile procedure based on a trichloroacetimidate methodology and peracetate sugar precursors. The final design opens possibilities for the preparation of a series of interesting analogs for further pharmacological optimization and development, including derivatives containing different saturated and polyunsaturated fatty acids (e.g., and ).