Clickable Surfaces for the Selective Recognition of Oligosaccharides

With the emergent role of protein glycosylation as a potential biomarker of disease, new technologies are required to selectively recognise unique glycan structures symptomatically expressed in disease states. Currently, glycan recognition is achieved through methods lacking high affinity and selectivity or through complex analytical methods and are poorly suited to clinical laboratories. In this thesis we propose an alternative glycan sensing strategy based on molecular self-assembly and imprinting of glycan ligands with phenyl boronic acid (PBA), imbuing selective oligosaccharide recognition to a surface. This strategy employs extensive use of the copper catalysed click reaction providing a simple highly biocompatible and adaptable self-assembled monolayer intended to form a foundation for future modifications. The synthesis and characterisation of various SAM monomers has been described here alongside azide functionalised-PBA CuAAC ligands and PBA terminated SAM monomers. SAMs formed with these were characterised for surface organisation and the CuAAC reaction yield established thus confirming reaction utility in functionalisation of alkyne terminated SAMs. Saccharide binding of PBA functional SAMs was then examined accounting for surface organisation between SAM monomer designs. Having determined a suitable SAM for functionalisation, we then produced a novel oligosaccharide-PBA imprinted surface demonstrating high selectivity between structurally different oligosaccharides.