Recent development of vaccines against cancers and infectious diseases has relied heavily on subunit antigen constructs. However the refined antigens are often less immunogenic, necessitating the use of adjuvants. Structurally defined synthetic adjuvants stimulating both Th1 and Th2 immune responses are extremely important to subunit vaccines, when a sufficiently potent cytotoxic T lymphocyte (CTL) response to antigens is desired. Herein we report our rational design and chemical synthesis of new saponin-type immune adjuvants. The step economical synthesis of the oligosaccharide portion of the adjuvants features a simple glycosylation method using only allyl glycosides as building blocks. Thus, in a one-pot fashion, an allyl glycoside is isomerized to the corresponding prop-1-enyl glycoside and its subsequent activation with NIS/TfOH in the presence of an allyl glycosyl acceptor leads to the formation of a new allyl glycoside. The new protocol could markedly simplify carbohydrate synthesis and improve overall synthetic efficiency.

Design and synthesis of structurally defined immune adjuvants

245th National Meeting (2013)

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