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UBC Theses and Dissertations

Towards the synthesis of Janus-AT phosphoramidites Liu, Wenbo


A Janus heterocycle is one kind of heterocycle that possesses hydrogen bonding donors or acceptors at both sides compared to regular nuclear bases. This provides an interesting synthetic target as well as a tool for testing an intriguing biological hypothesis related to DNA recognition, namely can both strands in the DNA duplex be recognized simultaneously by a single oligomeric strand of Janus heterocycles? In order to test this hypothesis, oligonucleotides containing at least one Janus heterocycle must be synthesized. One challenge involved in the synthesis of oligonucleotides with a Janus heterocycle is the extremely low solubility of Janus heterocycle phosphoramidites in organic solvents, namely MeCN. To solve the solubility issue, two sulfone-masked Janus-AT phosphoramidites were designed and constructed in this thesis. In addition to questions of solubility, the other obstacle related with Janus heterocycle oligonucleotide construction is the potential for deglycosylation, analogous to depurination, which might occur under the acidic conditions used during solid phase synthesis of oligonucleotides. The carbocyclic analog of deoxyribose, in lieu of 2-deoxyribose was employed to construct Janus heterocycle phosphoramidites in order to obviate the potential for depurination-like elimination of the nucleobase from the sugar.

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