Aromatic-carbohydrate amphiphiles and self-assembly into supramolecular glycostructures

Abstract

Carbohydrate-conjugated aromatic glycostructures, constituted with a diverse set of carbohydrate and aromatic moieties, possess a strong tendency to self-assemble in aqueous solutions under appropriate conditions. The self-assembly of such aromatic-carbohydrate amphiphiles is driven primarily by π-stacking, which envelops the aromatic moieties and hydrogen bonding interactions between the carbohydrate moieties. The self-assembled structures possessing multiple copies of carbohydrates on their surface mimic multivalent presentations, relevant to high avidity lectin binding, applications in drug delivery, cell imaging and more. This review focuses on the advantages of using self-assembly of carbohydrate-based aromatic amphiphiles in a bottom-up approach to generate diverse supramolecular glycostructures, possessing molecular and supramolecular chiralities. Advantages of this approach are the use of well-defined and low molecular weight building blocks to generate supramolecular structures with tunable properties, as well as the development of stimuli-responsive glycomaterials.