The synthesis of some deoxygenated analogues of early intermediates in the biosynthesis of glycosylphosphatidylinositol (GPI) membrane anchors

Alexander P.  Dix; Charles N.  Borissow; Michael A. J.  Ferguson; John S.  Brimacombe

doi:10.1016/j.carres.2004.02.026

The synthesis of some deoxygenated analogues of early intermediates in the biosynthesis of glycosylphosphatidylinositol (GPI) membrane anchors

Alexander P. Dix, Charles N. Borissow, Michael A. J. Ferguson, John S. Brimacombe

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6 Citations (Scopus)

Abstract

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.

Original language	English
Pages (from-to)	1263-1277
Number of pages	15
Journal	Carbohydrate Research
Volume	339
Issue number	7
DOIs	https://doi.org/10.1016/j.carres.2004.02.026
Publication status	Published - 2004

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@article{b35b7068d5ea4e67b6b0b434fa20339a,

title = "The synthesis of some deoxygenated analogues of early intermediates in the biosynthesis of glycosylphosphatidylinositol (GPI) membrane anchors",

abstract = "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.",

author = "Dix, {Alexander P.} and Borissow, {Charles N.} and Ferguson, {Michael A. J.} and Brimacombe, {John S.}",

year = "2004",

doi = "10.1016/j.carres.2004.02.026",

language = "English",

volume = "339",

pages = "1263--1277",

journal = "Carbohydrate Research",

issn = "0008-6215",

publisher = "Elsevier",

number = "7",

}

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 -

The synthesis of some deoxygenated analogues of early intermediates in the biosynthesis of glycosylphosphatidylinositol (GPI) membrane anchors

Abstract

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