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

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-?-d-sulfoquinovosylglycerol (?-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).

SUBMITTER: Manzo E

PROVIDER: S-EPMC5618427 | biostudies-literature | 2017 Sep

REPOSITORIES: biostudies-literature

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

Manzo Emiliano E Fioretto Laura L Pagano Dario D Nuzzo Genoveffa G Gallo Carmela C De Palma Raffaele R Fontana Angelo A

Marine drugs 20170920 9

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 ...[more]

PMID: 28930144

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Vaccine Adjuvants Derived from Marine Organisms.

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Identification of a New Chemical Class of Antimalarials, ACT-213615

2012-07-20 | GSE39485 | GEO

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