| Proteins are in a category all their own as supramolecular entities enriched with both chirality and functionality. Inspired by them, we have created a new class of building blocks, called Bis-Amino Acids, for making molecules several kilodaltons in size that possess high degrees of both functionality and chirality. Bis-amino acids can assemble into shape-programmable macromolecules, called Spiroligomers that connect through pairs of amide bonds. They serve as water-soluble, rigid scaffolds capable of presenting collections of functional groups in different spatial orientations by virtue of their sequence, shape and stereochemistry of each chiral building block.;This dissertation utilizes these unique building block as scaffolding for the presentation of functional groups in localized domains. A short spiroligomer sequence is used to presents a donor and acceptor pair facially for measuring electron-transfer in water. The same cleft motif is used to present a pair of hydrogen bonding donors to catalyze an aromatic Claisen rearrangement. Methods are developed to improve and expand the chemistry to make the bis-amino acids as well as their assembly into spiroligomers. Lastly, spiroligomers are utilized as intermediate building materials forming sequences of two and three connected by short, flexible linkers and cross-linked them into assemblies. We envision the use of these macromolecules, called "Fauxteins" to position multiple functional groups over large surface areas for mimicry of protein-protein interactions, recreation of complex active sites of enzymes, and form unique, chiral pockets for host-guest molecular recognition. |
