Bio-Organic Chemistry Unit, CNR-Institute of Biomolecular Chemistry, Via Campi Flegrei 34, IT-80078 Pozzuoli, 80078 Napoli, Italy.
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.
Mar Drugs. 2017 Sep 20;15(9):288. doi: 10.3390/md15090288.
Vaccines play a primary role in the protection of human health by preventing infectious and chronic diseases. Recently we have reported 1,2--distearoyl-3--β-d-sulfoquinovosylglycerol (β-SQDG18), here named Sulfavant A (), 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 , including a discussion of chemical determinants of the activity and the major technical hurdles we faced during the study. Synthesis of Sulfavant A () 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., and ).
疫苗通过预防传染病和慢性病，在保护人类健康方面发挥着主要作用。最近，我们报道了 1,2--二硬脂酰基-3--β-d-磺基奎诺糖基甘油（β-SQDG18），在这里将其命名为 Sulfavant A（），它在体外和体内试验中表现出作为新型分子佐剂的良好特性。在本手稿中，我们提供了有关制备的详细信息，包括对活性的化学决定因素的讨论以及在研究过程中我们面临的主要技术障碍。Sulfavant A（）的合成是通过基于三氯乙酰亚胺酯方法和过乙酸酯糖前体的通用程序实现的。最终的设计为进一步的药理学优化和开发制备一系列有趣的类似物提供了可能性，包括含有不同饱和和多不饱和脂肪酸的衍生物（例如和）。
