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

Research output: Contribution to journal › Article › peer-review

7 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

Access to Document

10.1016/j.carres.2004.02.026

Cite this

@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

Access to Document

Fingerprint

Cite this