Synthesis and applications of sequence-defined oligo(amidoamines) to mimic and modulate bioadhesion processes

Adhesion phenomena are crucial in numerous biological interactions and are often controlled by biomacromolecules such as proteins or polysaccharides. In order to better understand but also to potentially control or modulate adhesion processes, we can apply biomimetic macromolecules. Previously, we have introduced the so-called solid phase polymer synthesis to allow for the straightforward preparation of different sequence-defined peptide- and glycomimetic macromolecules. Through the stepwise assembly of tailor-made building blocks, we obtain oligo(amidoamine) scaffolds that can be used for the site-specific introduction of various functional groups, including bioligands and reactive moieties such as catechol units. We can control the types, number and positions of these different functional moieties as well as the architecture of the resulting macromolecule. This talk will highlight two recent examples on how we used solid phase polymer synthesis to create model systems and modulators of bioadhesion. In the first example, catechol groups – an important component of many natural glues – together with amine and amide groups are combined in a sequence-defined fashion using our scaffolds and investigated for their adhesion towards glass surfaces. Surprisingly, it is not only the combination of catechols and amines/amides but also their sequence that leads to a synergistic effect and highly improved adhesion properties. In the second example, we combine the catechol unit with carbohydrate ligands to create efficient inhibitors of bacterial adhesion. Notably, we observed carbohydrate ligands can bind to the adhesion sites of the bacteria but only upon addition of the catechol units is the binding site blocked permanently.