TY - JOUR
T1 - The synthesis of some deoxygenated analogues of early intermediates in the biosynthesis of glycosylphosphatidylinositol (GPI) membrane anchors
AU - Dix, Alexander P.
AU - Borissow, Charles N.
AU - Ferguson, Michael A. J.
AU - Brimacombe, John S.
PY - 2004
Y1 - 2004
N2 - 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-oxylo-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. (C) 2004 Published by Elsevier Ltd.
AB - 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-oxylo-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. (C) 2004 Published by Elsevier Ltd.
U2 - 10.1016/j.carres.2004.02.026
DO - 10.1016/j.carres.2004.02.026
M3 - Article
C2 - 15113663
SN - 0008-6215
VL - 339
SP - 1263
EP - 1277
JO - Carbohydrate Research
JF - Carbohydrate Research
IS - 7
ER -