Synthesis of part of a proposed insulin second messenger glycosylinositol phosphate and the inner core of glycosylphosphatidylinositol anchors

✍ Scribed by Per J. Garegg; Peter Konradsson; Stefan Oscarson; Katinka Ruda

• Publisher: Elsevier Science
• Year: 1997
• Tongue: French
• Weight: 575 KB
• Volume: 53
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(97)10238-1

✦ Synopsis

Synthesis of 6-O-(2-amino-2-deoxy-a-D-glucopyranosyl)-~~o-inositol l-phosphate, an inner core structure found in various glycosylphosphatidylinositols, and the corresponding 1,Zcyclic phosphate, proposed as part of an insulin second messenger glycosylinositol phosphate, is described. Chirality in the inositol part of the molecule was achieved by the use of a known D-camphor a&al intermediate. The glycosylation used 4-O-allyl-2-azido-3,6-di-O-benzyl-2-deoxy-a-D-ghtcopyranosyl fluoride as glycosyl donor. The ally1 group can be chemoselectively removed, opening a route to oligosaccharides bound to the 4-position of the glucosamine unit. The phosphorylation was accomplished by the phosphoramidate procedure.