期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 15, 期 40, 页码 10423-10431出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.200901077
关键词
carbohydrates; drug design; glycoproteins; lectins; molecular modeling; NMR spectroscopy
资金
- Ministry of Science and Innovation of Spain [CTQ2006-10874-C02-01/BQU]
- EC [MCRTN-CT-2005-19561]
- Ente Cassa di Risparmio di Firenze
Efficient cycloaddition of a silylidene-protected galactal with a Suitable heterodiene yielded the basis for a facile diastereoselective route to a glycopeptide-mimetic scaffold. Its carbohydrate part was further extended by beta 1-3-linked galactosylation. The pyranose rings retain their C-4(1) chair conformation, as shown by molecular modeling and NMR spectroscopy, and the typical exo-anomeric geometry was observed for the disaccharide. The expected bioactivity was ascertained by saturation-transfer-difference NMR spectroscopy by using the galactoside-specific plant toxin viscumin as a model lectin. The experimental part was complemented by molecular docking. The described synthetic route and the strategic combination of computational and experimental techniques to reveal conformational properties and bioactivity establish the prepared alpha-O-linked glycopeptide mimetics as promising candidates for further exploitation of this scaffold to give O-glycans for lectin blocking and vaccination.
作者
我是这篇论文的作者
点击您的名字以认领此论文并将其添加到您的个人资料中。
推荐
暂无数据