Chemical Synthesis of Marine-Derived Sulfoglycolipids, a New Class of Molecular Adjuvants
AbstractVaccines 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). View Full-Text
- Supplementary File 1:
Supplementary (PDF, 679 KB)
Share & Cite This Article
Manzo, E.; Fioretto, L.; Pagano, D.; Nuzzo, G.; Gallo, C.; De Palma, R.; Fontana, A. Chemical Synthesis of Marine-Derived Sulfoglycolipids, a New Class of Molecular Adjuvants. Mar. Drugs 2017, 15, 288.
Manzo E, Fioretto L, Pagano D, Nuzzo G, Gallo C, De Palma R, Fontana A. Chemical Synthesis of Marine-Derived Sulfoglycolipids, a New Class of Molecular Adjuvants. Marine Drugs. 2017; 15(9):288.Chicago/Turabian Style
Manzo, Emiliano; Fioretto, Laura; Pagano, Dario; Nuzzo, Genoveffa; Gallo, Carmela; De Palma, Raffaele; Fontana, Angelo. 2017. "Chemical Synthesis of Marine-Derived Sulfoglycolipids, a New Class of Molecular Adjuvants." Mar. Drugs 15, no. 9: 288.
Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.