Preparation of functional polypeptides via methionine alkylation

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Polypeptides are chemically synthesized mimics of natural proteins, and offer many advantages as mimics of biological materials for medical uses. Since they are synthetic, these materials are free from biological impurities that may have undesirable properties, and also are prepared free from pathogens that may be carried in biologically derived materials. Chemical modification of polypeptides is a method to enhance the properties of these materials for eventual use in applications such as drug delivery vehicles, regenerative medicine scaffolds, or as medical diagnostic devices. This research project is focused on improving upon the current state of the art for chemical polypeptide modification to make these processes more economical and broader in scope. Success of this project is expected to provide general methods that may be used downstream in a number of medically important applications. In this project, Prof. Timothy Deming at the University of California Los Angeles plans to include underrepresented groups, teach and train graduate and undergraduate students, and disseminate research findings in publications and presentations. Under the support of the Macromolecular, Supramolecular and Nanochemistry Program of the NSF Division of Chemistry, Prof. Deming conducts research to (i) develop practical, selective methods to chemically modify polypeptides, and (ii) develop this chemistry for controlled attachment and release of molecules from polypeptides. More specifically, his research group plans to explore and develop the reactions of methionine residues in polypeptides to prepare aklylated methionine sulfonium derivatives. The key challenge of this project is to determine how alkylating reagent structure affects the chemistry and stability of the resulting methionine sulfonium groups. The knowledge gained from these studies can allow fine tuning of polypeptide functional group reactivity that may be valuable for downstream specific uses, e.g. in the controlled release of drugs, and is expected to lay groundwork for development of a new class of functional biopolymers.