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Updated: Jul 16, 2026

Modification and Functionalization of the Guanidine Group by Tailor-made Precursors
Published on: April 27, 2017
Convergent synthesis of a GPI containing an acylated inositol
1Contribution from the Department of Chemistry, Case Western Reserve University, Cleveland, Ohio 44106-7078.
Abstract:
A GPI of sperm CD52 was synthesized by a highly convergent procedure, representing the first chemical synthesis of a complex GPI having an acylated inositol. The presence of a large acyl group resulted in unusual properties and reactions of the relevant intermediates, which gave rise to a number of problems. To overcome the problems and achieve the target molecule, a new synthetic strategy was developed. First, the pseudodisaccharide of 2-O-palmitoylinositol was phospholipidated, and then the trimannose segment and the phosphoethanolamine group were sequentially attached. Global deprotection eventually afforded the sperm CD52 GPI. The method may be useful for the synthesis of other GPIs having an acylated inositol.
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