Mannosylated saponins based on oleanolic and glycyrrhizic acids. Towards synthetic colloidal antigen delivery systems

…, CM Hayman, SM Hook, WT McBurney, T Rades…

Index: Daines, Alison M.; Greatrex, Ben W.; Hayman, Colin M.; Hook, Sarah M.; McBurney, Warren T.; Rades, Thomas; Rendle, Phillip M.; Sims, Ian M. Bioorganic and Medicinal Chemistry, 2009 ,  vol. 17,  # 14  p. 5207 - 5218

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Citation Number: 9

Abstract

Immunostimulatory saponin based colloidal antigen delivery systems show promise as adjuvants for subunit vaccines. For this reason, allyl oleanolate was glycosylated at the 3- position using trichloroacetimidate donors to give monodesmodic saponins following deprotection. Bisdesmodic saponins were synthesized by double glycosylation at the 3-and 28-positions of oleanolic acid. When formulated together with cholesterol and ...