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Mar. Drugs 2017, 15(9), 288; doi:10.3390/md15090288

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

1
Bio-Organic Chemistry Unit, CNR-Institute of Biomolecular Chemistry, Via Campi Flegrei 34, IT-80078 Pozzuoli, 80078 Napoli, Italy
2
Department of Internal and Experimental Clinic, Clinical Immunology and Allergology, University of Campania, c/o II Policlinico (Bd. 3), Via S.Pansini 5, 80131 Napoli, Italy
*
Author to whom correspondence should be addressed.
Received: 27 July 2017 / Revised: 29 August 2017 / Accepted: 11 September 2017 / Published: 20 September 2017
(This article belongs to the Special Issue Target Identification of Marine Products)
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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-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
Keywords: glycolipids; sulfolipid; vaccine; adjuvant; immunology; innate immunity; dendritic cells; immunogenic lipid; Sulfavant A glycolipids; sulfolipid; vaccine; adjuvant; immunology; innate immunity; dendritic cells; immunogenic lipid; Sulfavant A
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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.

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