Barron, Andrew R.2013-03-082013-03-082011Strom, T. Amanda. "C60 Amino Acids and Peptides." (2011) Diss., Rice University. <a href="https://hdl.handle.net/1911/70455">https://hdl.handle.net/1911/70455</a>.https://hdl.handle.net/1911/70455Since the discovery of the buckyball in 1985, researchers have imagined its potential in fields ranging from materials science to medicinal chemistry. The unique size, shape and hydrophobicity of C 60 fullerene endow it with the ability to interact with biological superstructures such as enzymes and membranes making it attractive as a potential pharmacophore. In this regard, we have developed a new, simple route to water soluble fullerene amino acids, both alkyl and aryl, through the dipolar addition of azido starting materials. The synthesis of our phenylalanine derivative, including the chromatographic purification, requires only one day for its completion. We have subsequently used our C 60 phenylalanine derivative in the synthesis of a series of C 60 peptides for the purposes of enzyme inhibition, specifically human immunodeficiency virus Type 1 protease, a critical viral enzyme responsible for the maturation of the virus and a popular target of medicinal chemists. We have demonstrated the ability of our C 60 amino acids and peptides to inhibit HIV-1 PR in a cell-free fluorescence based assay at low nanomolar concentrations. Graphite, or specifically graphene, has recently come to the forefront of nanomaterials research due to it similar scale, properties, and reaction pathways as other more costly carbon nanostructures such as carbon nanotubes. We have demonstrated the high yield functionalization of graphitic starting materials through the thermal decomposition of azido amino acids to their corresponding nitrene. The result is an inexpensive, highly functionalized, carbon based scaffold.126 p.application/pdfengCopyright is held by the author, unless otherwise indicated. Permission to reuse, publish, or reproduce the work beyond the bounds of fair use or other exemptions to copyright law must be obtained from the copyright holder.Pure sciencesFullerenesAmino acidsProtease inhibitorsGrapheneOrganic chemistryThesisStromTTHESIS CHEM. 2011 STROM