Date of Award


Degree Type


Degree Name

Master of Science




Dr. Robert H. E. Hudson


The synthesis o f peptide nucleic acid (PNA) is o f interest for their binding to nucleic acids and their potential for gene-based diagnostics and therapy. This thesis describes the synthesis of Fmoc/Boc protected PNA monomers for thymine (T), 2,6-diaminopurine (DAP), and 2-aminopurine (2AP). The oligomerization and selectivity over mismatches in DNA were studied with 2AP showing a higher selectivity for T over DAP (11.5 °C vs 6 °C). Inclusion of 2AP allowed fluorometric monitoring o f the denaturation o f PNA:DNA hybrid duplexes.. The synthesis o f sin azide-containing PNA monomer was completed and successfully incorporated into PNA. A solid phase copper azide-alkyne cycloaddition was performed in , quantitative yield. The synthesis of alkynes to be incorporated into the PNA is described. The syntheses of the monomers described will make unusual PNAs more accessible, allowing the study o f their unique properties



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