<p> Attempts to prepare silicone oligonucleotide copolymers are complicated by the large
difference in hydrophobicity in the two materials. Two approaches were followed to
overcome this challenge. Initially, highly sterically hindered tetraisopropyldisiloxanes
were used to bind 5'-0-(4,4'-dimethoxytrityl)-thyrnidine at the 5'-0H. These compounds
proved to be hydrolytically more stable than the analogous dimethylsiloxane compounds,
which were also prepared. Alternatively, Si-C bonds, which are hydrolytically stable, can
be used to bind the two species together. Introduction of allyl ether by traditional
Williamson conditions was followed by hydrosilylation with hydride terminated (Si-H)
silicone, catalyzed by using platinum complexes, to give the nucleoside-functionalized
silicone. We also introduced an epoxy group to one end of a silicone chain and found it to
be stable to hydrolysis. Once the epoxy group binds nucleoside-functionalized silicone to
solid phase, it is expected that the nucleoside-functionalized silicone via a trimethylene
spacer linkage might be a starter for preparation of oligonucleotide-functionalized
silicones in future work. </p> / Thesis / Master of Science (MSc)
| Identifer | oai:union.ndltd.org:mcmaster.ca/oai:macsphere.mcmaster.ca:11375/19343 |
| Date | 02 1900 |
| Creators | Guo, Kui |
| Contributors | Brook, M. A., Chemistry |
| Source Sets | McMaster University |
| Language | English |
| Detected Language | English |
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