Though the self-assembly and gelation of dipeptides has been well established, there remains an interest in developing new supramolecular peptide gelators capable of reversibly incorporating target molecules into the gel network. Specifically, as targeted drug delivery is an attractive application for these biomaterials, the development of new methods to control the incorporation and release of these drugs is essential. To achieve this, we have designed a supramolecular gelator with two main features: (1) a diphenylalanine unit to induce gelation upon self-assembly, and (2) a boronic acid unit to recognize and bind biologically relevant diols. Here, we report the synthesis of a dipeptide-boronic acid conjugate that can form gels in aqueous binary mixtures. We successfully synthesized this gelator in three steps with a high yield and fully characterized the product by 1H, 13C, and 11B NMR. We found that this dipeptide forms a transparent, self-supporting gel in a 50:50 ethanol: water mixtures. Additionally, we have shown that the boronic acid-dipeptide binds diols through a boronate linkage using an alizarin red S displacement assay. In the future, we will continue to explore the incorporation and controlled release of biologically relevant diols, such as the Parkinson’s drug L-DOPA.

Supramolecular gels made from dipeptide-boronic acids

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.