Synthetic glycopolypeptides are versatile glycopolymers used to conceive bioinspired nanoassemblies. In this work, novel amphiphilic glycopolypeptides were designed to incorporate lactose or galactan in order to prepare polymeric nanoassemblies with sizes below 50 nm. The bioactivity of the two different outer surface sugar units was evaluated by defining glycan relative binding affinities to human galectins 1 and 3. A specific multivalent effect was found only for polymeric nanoparticles displaying galactan with a significant increase of the binding activity as compared to free glycan in solution. Such synthetic designs present great potential as therapeutic tools to address galectin related pathologies.