Convergent synthesis of a GPI containing an acylated inositol.
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.
Xue
Jie
J
Contribution from the Department of Chemistry, Case Western Reserve University, Cleveland, Ohio 44106-7078.
Guo
Zhongwu
Z
D000215:Acylation; D015703:Antigens, CD / Q000737:chemistry; D000951:Antigens, Neoplasm / Q000737:chemistry; D000074301:CD52 Antigen; D002240:Carbohydrate Sequence; D006023:Glycoproteins / Q000737:chemistry; D017261:Glycosylphosphatidylinositols / Q000138:chemical synthesis* / Q000737:chemistry; D006801:Humans; D008297:Male; D008969:Molecular Sequence Data; D013094:Spermatozoa / Q000737:chemistry
D015703:Antigens, CD; D000951:Antigens, Neoplasm; D000074301:CD52 Antigen; C000613862:CD52 protein, human; D006023:Glycoproteins; D017261:Glycosylphosphatidylinositols