[show abstract][hide abstract] ABSTRACT: Sperm CD52 GPI anchor and its derivatives containing different carbohydrate chains were prepared in a highly convergent fashion starting from the same properly protected phospholipidated pseudodisaccharide. Coupling this common key intermediate to various oligosaccharyl donors quickly afforded the framework of the synthetic targets, which was followed by global deprotection to furnish the desired structures. Preliminary studies on the biological properties of the synthetic GPI derivatives indicated that both the intact GPI anchor and the free phospholipidated pseudodisaccharide interacted strongly with CAMP factor, a pore-forming bacterial toxin.
Carbohydrate Research 08/2008; 343(10-11):1718-29. · 2.04 Impact Factor
[show abstract][hide abstract] ABSTRACT: A fully phosphorylated GPI anchor (1) of the CD52 antigen was synthesized by a highly convergent strategy. After a trimannose and a phospholipidated pseudodisaccharide were prepared separately, they were coupled together to form the GPI core, which was then phosphorylated to introduce two phosphoethanolamine moieties in one step to afford CD52 GPI in its fully protected form. Finally, global deprotection of the product resulted in 1.