The synthesis of some deoxygenated analogues of early intermediates in the biosynthesis of glycosylphosphatidylinositol (GPI) membrane anchors.
Syntheses are described of 2-azido-4,6-di-O-benzyl-2,3-dideoxy-d-ribo-hexopyranosyl fluoride, 6-O-acetyl-2-azido-3-O-benzyl-2,4-dideoxy-d-xylo-hexopyranosyl fluoride and 2-azido-3,4-di-O-benzyl-2,6-dideoxy-d-glucopyranosyl fluoride. These glycosyl donors were coupled with the acceptor 1d-2,3,4,5-tetra-O-benzyl-1-O-(4-methoxybenzyl)-myo-inositol and the alpha-coupled products were transformed into alpha-d-3dGlcpN-PI, alpha-d-4dGlcpN-PI and alpha-d-6dGlcpN-PI by way of the H-phosphonate route. Brief mention is made of the biological evaluation of these deoxy-sugar analogues and their N-acetylated forms as candidate substrate/inhibitors of the N-deacetylase and alpha-(1-->4)-d-mannosyltransferase activities present in trypanosomal and HeLa (human) cell-free system.
Dix
Alexander P
AP
School of Life Sciences (Chemistry), Carnelley Building, University of Dundee, Dundee DD1 4HN, UK.
Borissow
Charles N
CN
Ferguson
Michael A J
MA
Brimacombe
John S
JS
D000818:Animals; D017261:Glycosylphosphatidylinositols / Q000096:biosynthesis* / Q000737:chemistry*; D006367:HeLa Cells; D006801:Humans; D008566:Membranes / Q000737:chemistry; D015394:Molecular Structure
D017261:Glycosylphosphatidylinositols