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-beta-D-sulfoquinovosylglycerol (beta-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).
Chemical Synthesis of Marine-Derived Sulfoglycolipids, a New Class of Molecular Adjuvants / Manzo, Emiliano; Fioretto, Laura; Pagano, Dario; Nuzzo, Genoveffa; Gallo, Carmela; De Palma, Raffaele; Fontana, A. - In: MARINE DRUGS. - ISSN 1660-3397. - 15:9(2017). [10.3390/md15090288]
Chemical Synthesis of Marine-Derived Sulfoglycolipids, a New Class of Molecular Adjuvants
Fontana A
2017
Abstract
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-beta-D-sulfoquinovosylglycerol (beta-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).File | Dimensione | Formato | |
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