The synthesis of the tertbutyldimethylsilyl derivatives of adenosine is described. The 2',5'-protected nucleosides were rapidly and easily prepared in relatively good yields. / The silylated nucleosides are easily incorporated into ribonucleotides using the fast and efficient dichlorophosphite method. The ribonucleotide GpCpApApCpCpA corresponding to the 3'-terminus of / (DIAGRAM, TABLE OR GRAPHIC OMITTED...PLEASE SEE DAI) / was successfully synthesized in a stepwise fashion. The stepwise and block condensation pathways were compared in the synthesis of CpCpCpCpC. The syntheses of A2'p5'A2'p5'A and other 2',5'- and symmetrically-linked ribonucleotides were readily accomplished. ('31)P NMR was very useful in elucidating the structure of the diribonucleoside monophosphates. A study of the effect of temperature and solvents on yield of final product is undertaken. Various phosphate protecting groups are also evaluated. / A suitable deprotection procedure is investigated and the identity of the phosphate linkages confirmed by enzyme degradations.
| Identifer | oai:union.ndltd.org:LACETR/oai:collectionscanada.gc.ca:QMM.68591 |
| Date | January 1981 |
| Creators | Theriault, Nicole. |
| Publisher | McGill University |
| Source Sets | Library and Archives Canada ETDs Repository / Centre d'archives des thèses électroniques de Bibliothèque et Archives Canada |
| Language | English |
| Detected Language | English |
| Type | Electronic Thesis or Dissertation |
| Format | application/pdf |
| Coverage | Doctor of Philosophy (Department of Chemistry) |
| Rights | All items in eScholarship@McGill are protected by copyright with all rights reserved unless otherwise indicated. |
| Relation | alephsysno: 000127668, proquestno: AAINK52148, Theses scanned by UMI/ProQuest. |
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