A Simple Model System for the Study of Carbohydrate-Aromatic Interactions

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• 作者：Giancarlo Terraneo ; Donatella Potenza ; Angeles Canales ; Jesus Jimé ; nez-Barbero ; Kim K. Baldridge ; Anna Bernardi
• 刊名：Journal of the American Chemical Society
• 出版年：2007
• 出版时间：March 14, 2007
• 年：2007
• 卷：129
• 期：10
• 页码：2890 - 2900
• 全文大小：692K
• 年卷期：v.129,no.10(March 14, 2007)
• ISSN：1520-5126

文摘

A molecular scaffold was identified which enables the establishment of intramolecular interactionsbetween a monosaccharide and a nearby phenyl ring. A group of molecules containing four differentmonosaccharides (glucose, galactose, N-acetyl-glucosamine, and N-acetyl-galactosamine) was synthesizedand used to investigate the extent and nature of this carbohydrate-arene interaction, as well as the effecton the overall 3D structure of the molecules involved. The sugar-aromatic distance was evaluated byrigorous NMR studies supported by molecular modeling and found to be constant throughout the series,independent of the nature of the sugar and of the conformational behavior of the fragment connecting thetwo elements. Ab initio calculations at the B3LYP/DZV(2d,p) level of theory enable the analysis of theelectronic nature of the interaction. The study shows that, given the opportunity, persistent intramoleculararomatic-sugar interactions can be established and can significantly influence overall molecular shapeand energetics. These results have important implications in the design of structural mimics of oligosaccharides.