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Chemical Synthesis of Marine-Derived Sulfoglycolipids, a New Class of Molecular Adjuvants.
Marine Drugs 2017 September 21
Vaccines play a primary role in the protection of human health by preventing infectious and chronic diseases. Recently we have reported 1,2- O -distearoyl-3- O -β-d-sulfoquinovosylglycerol (β-SQDG18), here named Sulfavant A ( 1 ), 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 1 , including a discussion of chemical determinants of the activity and the major technical hurdles we faced during the study. Synthesis of Sulfavant A ( 1 ) 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., 17 and 22 ).
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