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Thesis (Ph. D.)--Auburn University. / Abstract. Vita. Includes bibliographical references (p. 110-125).

D.Sc. (Chemistry) / Please refer to full text to view abstract

by Francis Yat Ping Kwong. / Thesis (Ph.D.)--Chinese University of Hong Kong, 1987. / Bibliography: leaves [135]-[152]

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A route to the synthesis of arabino and xylonucleosides is described. This route takes advantage of highly selective ribonucleoside hydroxyl protection procedures which have recently been developed. The route is straightforward and broadly applicable. It may be applied to both purine and pyrimidine nucleosides. Synthesis, deprotection, and characterisation of the target compounds are described. The work is compared to that of others in the field. / A novel class of oligonucleotide analogues is described. In this group, the phosphorus atom of the internucleotide link is replaced by silicon. The synthesis of both oligothymidine and oligo-2$ sp prime$-deoxyadenosine nucleotide analogues of this class is described. Various substituents at silicon are employed, and oligonucleotide analogs of up to six units long are synthesised, characterised and deprotected. The circular dichroism spectra of the deprotected hexamers is presented.

The synthesis of novel nucleoside and nucleotide analogues in which the sugar moiety is replaced by an aliphatic chain is described. The acyclic analogue of adenosine was tested as both a substrate and an inhibitor of adenosine deaminase while the interaction of some dinucleoside monophosphate analogues with spleen and snake venom phosphodiesterase is reported. Some mention is made of the solution conformation of these acyclic derivatives. / The utility of the methyl group as a phosphate protecting group in oligonucleotide synthesis was reinvestigated and the preparation of some interesting 2', 5' linked trinucleoside diphosphate analogues of adenosine, with the methyl moiety as phosphate masking group, was undertaken. A novel approach to the cleavage of phosphate methyl esters is discussed. / A facile fluoride ion mediated preparation of alkylated nucleoside base fragments was discovered. This procedure led to high isolated yields of a variety of N-alkylated purines and pyrimidines.

Thesis (Ph. D.)--University of Texas at Austin, 2004. / Supervisor: Kenneth A. Johnson. Vita. Includes bibliographical references.