Chemo-enzymatic synthesis of a divalent sialyl Lewisx ligand with restricted flexibility

被引:8
作者
Bintein, F [1 ]
Augé, C [1 ]
Lubineau, A [1 ]
机构
[1] Univ Paris 11, UMR 8614, Lab Chim Organ Multifonct, F-91405 Orsay, France
关键词
chemo-enzymatic synthesis; divalent sialyl Lewis(x); selectin ligand; cooperativity; cluster effect;
D O I
10.1016/S0008-6215(03)00129-0
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
To study the influence of the entropic factor in cluster cooperative effects, a divalent sialyl Lewis(x) ligand with restricted flexilbility was chemo-enzymatically synthesized. First, a cyclized precursor with both glucosamine residues bridged together by a succinyl group was readily obtained in 42% yield by treatment of 2,2-bis(benzyloxymethyl)-1,3-bis(3,4,6-tri-O-acetyl-2-amino-2-deoxy-beta-D-glucopyranosyloxy)-propane with succinyl chloride. After deacetylation, this precursor was subjected to stepwise enzymatic elongation utilizing successively, soluble galactosyltransferase, then recombinant sialyltransferase and fucosyltransferase; the latter enzymes immobilized on Ni2+-Agarose, to afford, after debenzylation, a divalent sialyl Lewis(+) ligand of restricted flexibility. in 45% overall yield. Following the same enzymatic sequence, a totally flexible ligand, required as a reference compound for evaluation of inhibitory activity toward selectins, was also prepared from 2,2(bis-benzyloxymethyl)-1,3-bis(2-acetamido-2-deoxy-beta-D-glucopyranosyloxy)-propane, as well as both related divalent Lewis' molecules lacking the sialic acids, the rigid one and the flexible one. (C) 2003 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:1163 / 1173
页数:11
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