Synthesis of Clickable Amphiphilic 1,3-Propanediol Dendrons

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Liang, Xiaoli
The Graduate School, Stony Brook University: Stony Brook, NY.
Biohybrid materials combine proteins or peptides with synthetic molecules to generate materials with complex functions. Proteins have functions such as enzymatic activity, signal generation/recognition, and materials transfer due to their well-defined structures. Conjugating polymers to proteins has produced nanostructured biohybrid materials. However, only a fraction of the proteins are functional. De novo designed peptides that form the functional part of a protein are interesting alternatives to proteins in biohybrid materials. Nanostructured biohybrid materials are obtained by conjugating liquid crystal mesogens or polymers to peptides. We are interested in making functional biohybrid materials by conjugating amphiphilic dendrons to de novo designed proteins. Amphiphilic 1,3-propanediol dendrons form lamellar or columnar organization in the crystalline phase. We hypothesize that biohybrid materials obtained by covalently attaching amphiphilic dendrons to the exterior of a de novo designed proteins will have lattice structures similar to those of the dendrons in the solid-state. To test this hypothesis, we need amphiphilic dendrons to conjugate to the protein. Two new amphiphilic 1,3-propanediol dendrons with azide apex groups have been synthesized. The iterative synthesis of amphiphilic 1,3-propanediol dendrons was improved by adopting the use of 15-crown-5 as a catalyst for the Williamson etherification step. The reactions require shorter time to reach completion, reduce the amount of mono-alkylated intermediates as byproducts, and avoid the use of DMF as a co-solvent. The two new compounds can be attached to de novo designed proteins by the copper-catalyzed azide-alkyne cycloaddition reaction.
47 pg.