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

Abstract

LewisX (Lex) antigen based carbohydrate–carbohydrate interactions are mediated by complexation of metal ions. Although theoretical studies about the influence of participating hydroxyl groups in the Lex trisaccharide head group (Galβ(1-4)[Fucα(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 Lex 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 Lex 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 Lex trisaccharides.