Our carbohydrate synthesis group chooses its targets based on an expectation of activity in immunological assays. The ultimate goal is to create vaccine platforms that can be tuned for any desired immunological outcome. In particular we synthesize glycolipid based delivery systems that can promote predominantly antibody (Th2) or predominantly Cytotoxic T-Lymphocytes -CTL (Th1) responses, or a Th1, Th2 balanced response. Our results show that at least in Ovalbumin mouse model systems specific synthetic glycolipids strongly bias the immune response towards CTL production. Such responses lead to protection in cancer models. The mechanism of immune activation is not known precisely particularly which cell surface receptors are involved but is reproducibly shown to promote long term immune memory. For this purpose we have developed a convenient promoter system for peracylthioglycoside donors based on NIS and a BF3-2trifluoroethanol solution that leads to very clean glycosylation reactions which allow for facile purification of otherwise difficult to purify glycolipids. This report focuses on the synthetic complications of handling ampipathic molecules and presents several solutions including phase transfer methodologies and purification procedures.

Synthetic Archaea derived glycolipids promote MHC class I activity

243rd National Meeting (2012)

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