Development of modification method for organic foldamers on the resin, used in the design of molecular probes, and assessment of its usefulness in the synthesis of the library of molecular probes

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Principal Investigator: Michał Jewgiński

Project financed by National Science Centre, Miniatura no 2018/02/X/ST5/02835

Start date: March 16th, 2019

Project duration: 12 months

Budget: 49 500 PLN

Abstract

Foldamers are chemical compounds made of bricks that are not used by nature daily. These compounds, due to their specific structure, tend to adopt well-defined secondary structures. The compounds proposed in the project belong to the group of oligoamide aromatic folders. Thanks to their predictable spatial structure and modular structure, it is possible to use them in the construction of molecular probes capable of recognizing molecular surfaces, e.g. surfaces of macromolecules of biocidal significance. However, this process, despite the use of molecular modeling design techniques, often requires the synthesis of libraries containing structural variations of one sequence. This process allows the selection of a system with the best affinity for the selected molecular surface. This approach requires the synthesis of each molecule from the beginning. The research project carried out allows for the introduction into the foldamer sequence of a quinoline derivative containing a bromine atom in position 4. Thanks to the presence of a bromine atom, it is possible to introduce any substituent containing a thiol group in its place. Due to this approach, the number of syntheses necessary to perform is reduced to the synthesis of the lead structure of the molecular probe containing the brominated monomer derivative in the tested position. The structure is then modified in the place of the presence of the bromine atom, giving the possibility of obtaining many derivatives of the same leader sequence.

The developed approach will accelerate the synthesis of extensive and diverse foldamer libraries, and thus allow more efficient testing of their interaction with selected molecular surfaces. This will allow faster identification of ligands able to interact effectively with selected macromolecules.