C-glycoside analogues of β-galactosylceramide with a simple ceramide substitute:: Synthesis and binding to HIV-1 gp120

被引：20

作者：

Augustin, LA

Fantini, J

Mootoo, DR

机构：

[1] CUNY Hunter Coll, Dept Chem, New York, NY 10021 USA

[2] Univ Paul Cezanne, Lab Biochim & Physicochem Membranes Biol, INRA, UMR 1111,Fac Sci & Tech St Jerome, F-13397 Marseille 20, France

来源：

BIOORGANIC & MEDICINAL CHEMISTRY | 2006年 / 14卷 / 04期

关键词：

galactosyl ceramide; C-glycoside; aza-C-glycoside gp120; oxocarbenium ion;

D O I：

10.1016/j.bmc.2005.09.044

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 synthesis and HIV-1 gp120 binding of C- and aza-C-glycoside analogues of beta-galactosylceramide (GalCer) that contain a simple C-17 hydrocarbon chain as a ceramide substitute are described. Both compounds originate from stearic acid, and a carbohydrate-derived thioacetal-alcohol, and their syntheses are potentially general for beta-C-galactosides and their aza-C-partners. They showed potent and specific affinity for gp120 in an assay based on the change of surface pressure when the glycolipid monolayers were exposed to Solutions of gp120. Interestingly, the aza-C-glycoside exhibited a significantly higher affinity than GalCer, whereas the C-glycoside was as active as GalCer. (c) 2005 Elsevier Ltd. All rights reserved.

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页码：1182 / 1188

页数：7

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