Date of Award


Document Type


Degree Name

Doctor of Philosophy (PhD)




In recent years, the understanding of the structure and functions of biological macromolecules has advanced rapidly, the result of which is a better mechanistic understanding of many biological processes. As an outgrowth of this understanding, organic molecules that react with biological macromolecules (DNA) or adopt conformations responsible for specific functions in biological macromolecules (peptides and proteins) have been synthesized and computational modeling studies performed. Polycyclic aromatic hydrocarbons (PAHs) and β-peptides are among synthetic organic compounds known to interact with natural biological macromolecules. This interaction may affect the specific biological functions of the biomacromolecules. A variety of synthetic methodologies have been employed in the synthesis of benzo[c]phenanthrene derivatives, single electron oxidation nucleoside adducts and deoxynucleoside derivatives (Part 1). In Part 2 heterogeneous backbone oligomers containing the β-amino acid, trans-2-aminocyclohexanecarboxylic acid (ACHC), and α-amino acids Ala, Phe, Val, Lys, and Tyr in an alternating sequence have been synthesized. Computational modeling studies have been applied in studying the diastereoselectivity of reaction intermediates in the PAH syntheses (Part 1), the interaction between the organic compounds and biomacromolecules (β-peptides with proteins Fos and Jun, Part 2), and the conformational preference (conformations of α/β-peptides, Part 2). Computational modeling based on molecular and quantum mechanical techniques were applied to complement the syntheses in Parts 1 and 2.