Synthesis of benzaldehyde-functionalized LewisX trisaccharide analogs for glyco-SAM formation

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• 作者：Sebastian Kopitzki ; Karim Akbari Dilmaghani ; Joachim Thiem
• 关键词：Carbohydrates ; LewisX antigen ; Glycosylation ; Cross metathesis
• 刊名：Tetrahedron
• 出版年：9 December, 2013
• 年：2013
• 卷：69
• 期：49
• 页码：10621-10636
• 全文大小：1557 K

文摘

LewisX (Le^x) antigen based carbohydrate-carbohydrate interactions are mediated by complexation of metal ions. Although theoretical studies about the influence of participating hydroxyl groups in the Le^x trisaccharide head group (Gal尾(1-4)[Fuc伪(1-3)]GlcNAc) could gave same rudimental information about the basic mechanism behind this interaction, a little is known about orientation and configuration of the hydroxyl groups required for the specific interaction mediated by Ca²⁺ complexation. Therefore, there is a need of non-natural derivatives to provide detailed information about the requirements for hydroxyl group arrangement in Le^x head group surface plasmon resonance and gold nanoparticle techniques have shown to be powerful tools to investigate carbohydrate-carbohydrate interactions. Benzaldehyde-functionalized glycans can be used for attachment to both gold nanoparticles and surface plasmon resonance sensor surfaces. Therefore, seven benzaldehyde equipped Le^x analogs including the natural trisaccharide were synthesized utilizing convergent approach. The derivatives were applied in ongoing carbohydrate-carbohydrate interaction studies by surface plasmon resonance experiments to prove theoretical postulate about the structural requirements of hydroxyl group arrangements in Le^x trisaccharides.