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    The Design and Synthesis of Peptidomimetic-Hybrids: Expanding Spiroligomers, Peptoids, and Proline

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    Genre
    Thesis/Dissertation
    Date
    2016
    Author
    Northrup, Justin David
    Advisor
    Schafmeister, Christian
    Committee member
    Voelz, Vincent
    Dobereiner, Graham
    Childers, Wayne E.
    Department
    Chemistry
    Subject
    Chemistry, Organic
    Hydantoin
    Peptide
    Peptidomimetic
    Peptoid
    Proline
    Spiroligomer
    Permanent link to this record
    http://hdl.handle.net/20.500.12613/3343
    
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    DOI
    http://dx.doi.org/10.34944/dspace/3325
    Abstract
    Binding to protein surfaces or shallow grooves with synthetic molecules poses a unique challenge, since this inherently requires large areas to facilitate interactions. Peptoids have been shown to interact with proteins, and combinatorial libraries of peptoids have been proven to be effective in discovering new ligands for protein binding. Unfortunately, most peptoids are flexible and lack the surface area required to compete with larger protein interactions. To combat these problems, we have created spiroligomers that have a rigid backbone, exhibit functionality comparable to proteins, and are resistant to proteases. To facilitate the rapid installment of spiroligomers into peptoid subunits, we required a more streamlined approach for functionalization of spiroligomers. To this end we applied a single-pot alkylation method, with which we installed over 25 unique functional groups onto different spiroligomer hydantoins. These spiroligomer hydantoins are spirocycles that possesses two stereocenters, of which we have complete control, as well as a protected proline amino acid. These new proline amino acids (enhanced prolines) have been incorporated into peptides via Fmoc-SPPS. Finally, we have functionalized these enhanced proline residues with another functional group and a protected primary amine, which allow for their use in peptoid synthesis. We developed methods to tether multiple spiroligomers together utilizing a peptoid backbone, as well as being able to incorporate spiroligomers into peptoid macrocycles. These spiroligomer-peptoid hybrids are large, diverse, and preorganized structures that have a large potential interacting surface area for binding to protein surfaces or shallow grooves.
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