Chemo-enzymatic supported synthesis of the 3-sulfated Lewisa pentasaccharide on a multimeric polyethylene glycol

被引:5
作者
Malleron, Annie [1 ]
Le Narvor, Christine [1 ]
机构
[1] Univ Paris 11, Equipe Glycochim Mol & Macromol, Lab Chim Organ Multifonctionnelle, CNRS,UMR 8182, F-91405 Orsay, France
关键词
chemo-enzymatic synthesis; multimeric support; glycosyltransferase; Selectins; cell adhesion; inflammation;
D O I
10.1016/j.carres.2008.01.005
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
The 3-sulfated Lewis(a) pentasaccharide was synthesized on multimeric-based polyethylene glycol support. Coupling of O-(2,3,4,6-tetra-O-acetyl-beta-D-galactopyranosyl)-(1 -> 3)-4,6-di-O-acetyl-2-deoxy-2-phthalimido-beta-D-glucopyranosyl trichloroacetimidate with (2,6-di-O-acetyl-beta-D-galactopyranosyl)-(1 -> 4)-(2,3,6-tri-O-acetyl-beta-D-glucopyranoside) bound onto the polymer afforded lacto-N-tetraose, which was then regioselectively sulfated at the 3-OH position of the terminal galactose using the stannylene procedure. Fucosylation of the sulfated tetrasaccharide was performed using an immobilized fucosyltransferase FucTIII to give the title compound after cleavage. (C) 2008 Elsevier Ltd. All rights reserved.
引用
收藏
页码:970 / 976
页数:7
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