Mimics of ganglioside GM1 as cholera toxin ligands:: replacement of the GalNAc residue

被引：33

作者：

Bernardi, A

Arosio, D

Manzoni, L

Monti, D

Posteri, H

Potenza, D

Mari, S

Jiménez-Barbero, J

机构：

[1] Univ Milan, Dipartimento Chim Organ & Ind, I-20133 Milan, Italy

[2] Univ Milan, Ctr Eccellenza, CISI, I-20133 Milan, Italy

[3] CNR, ISTM, I-20133 Milan, Italy

[4] CSIC, Ctr Invest Biol, Dept Estructura & Func Prot, E-28006 Madrid, Spain

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2003年 / 1卷 / 05期

关键词：

D O I：

10.1039/b210503a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Two new cholera toxin (CT) ligands (4 and 5) are described. The new ligands were designed starting from the known GM1 mimics 2 and 3 by replacement of their GalNAc residue with the C4 isomer GlcNAc. As predicted by molecular modelling, the conformational properties of the equivalent pairs 2-4 and 3-5 are very similar and their affinity for CT is of the same order of magnitude. NMR experiments have also proved that 5 occupies the GM1-binding site of the toxin and have revealed its bound conformation.

引用

页码：785 / 792

页数：8

共 35 条

[1] 3-DIMENSIONAL STRUCTURE OF THE OLIGOSACCHARIDE CHAIN OF GM1 GANGLIOSIDE REVEALED BY A DISTANCE-MAPPING PROCEDURE - A ROTATING AND LABORATORY FRAME NUCLEAR OVERHAUSER ENHANCEMENT INVESTIGATION OF NATIVE GLYCOLIPID IN DIMETHYL-SULFOXIDE AND IN WATER DODECYLPHOSPHOCHOLINE SOLUTIONS [J].