Synthesis and biological evaluation of sperm CD52 GPI anchor and related derivatives as binding receptors of pore-forming CAMP factor

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. (C) 2008 Elsevier Ltd. All rights reserved.