UBC Theses and Dissertations

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UBC Theses and Dissertations

Synthesis of a peptide nucleic acid oligomer of a Janus heterocycle Hasan, Syed


This thesis describes the oligomerization of the Janus AT heterocycle on a peptide nucleic acid scaffold, a molecule that is capable of concurrently hydrogen bonding with adenine and thymine. An oligonucleotide incorporating this moiety should form sequence specific Watson-Crick based triplexes with DNA by strand invasion. Initially, the synthesis of a diamino Janus AT peptide nucleic acid monomer was attempted, but the monomer was too insoluble for solid phase synthesis. To curtail this issue, attempts were made to synthesize a more hydrophobic surrogate, wherein the exocyclic amines were masked. The synthesis of an undecamer was then undertaken, wherein the Janus monomer was alternated with a 6-methyluracil spacer. Lastly, a dodecamer of 6MU was synthesized to examine its biophysical properties in the context of base pairing with DNA.

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