The influence of the aromatic aglycon of galactoclusters on the binding of LecA: a case study with O-phenyl, S-phenyl, O-benzyl, S-benzyl, O-biphenyl and O-naphthyl aglycons

被引：25

作者：

Casoni, Francesca ^{[1
]}

Dupin, Lucie ^{[2
]}

Vergoten, Gerard ^{[3
]}

Meyer, Albert ^{[1
]}

Ligeour, Caroline ^{[1
]}

Gehin, Thomas ^{[2
]}

Vidal, Olivier ^{[3
]}

Souteyrand, Eliane

Vasseur, Jean-Jacques ^{[1
]}

Chevolot, Yann ^{[2
]}

Morvan, Francois ^{[1
]}

机构：

[1] Univ Montpellier 2, IBMM, CNRS, UMR 5247,UM1,UM2,ENSCM, F-34095 Montpellier, France

[2] Univ Lyon, Inst Nanotechnol Lyon, CNRS, Site Ecole Cent Lyon,UMR 5270, F-69134 Ecully, France

[3] Univ Lille 1, UGSF, UMR 8576, F-59655 Villeneuve Dascq, France

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2014年 / 12卷 / 45期

关键词：

AERUGINOSA LECTIN LECA; PSEUDOMONAS-AERUGINOSA; BACTERIAL LECTIN; PA-IL; CARBOHYDRATE MICROARRAY; FORCE-FIELD; DIVALENT INHIBITORS; HIGH-AFFINITY; GLYCOCLUSTERS; GALACTOSE;

D O I：

10.1039/c4ob01599a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A library of 24 new mannose-centered tetragalactoclusters with four different linkers (di- and triethyleneglycol with phosphodiester or phosphorothioate linkages) and six different aromatic aglycons (O-phenyl, S-phenyl, O-benzyl, S-benzyl, O-biphenyl and O-naphthyl) was synthesized. Their interactions with LecA were evaluated on a DNA Directed Immobilization (DDI) based glycocluster array allowing the determination of their IC50 against lactose and the evaluation of their dissociation constant (K-d). Finally, the docking simulations confirm the experimental results and demonstrated that the better affinity of O-biphenyl-and O-naphthyl-galactoside is due to a double interaction between the aromatic ring and the histidine 50 and proline 51 of LecA.

引用

页码：9166 / 9179

页数：14

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