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Nucleoside phosphorothioates
dc.contributor.advisor | Magill, J. M. | |
dc.creator | Mariano, Debra Dunaway | |
dc.date.accessioned | 2020-01-08T18:22:53Z | |
dc.date.available | 2020-01-08T18:22:53Z | |
dc.date.created | 1976 | |
dc.date.issued | 1975 | |
dc.identifier.uri | https://hdl.handle.net/1969.1/DISSERTATIONS-183458 | |
dc.description.abstract | The nucleoside-thiophosphorylating properties of the two phosphorus-thioxy anions, thiophosphate and dithiophosphate, were investigated. The heating of monoanionic thiophosphate with the nucleosides thymidine and 2 ':3'-O-ethoxymethyleneadenosine in anhydrous dimethyl formamide results in the formation thymidine 3' (5')-0-phosphorothioates and adenosine 5 '-0-phosphorothioate, respectively. From a detailed study of the thymidine reaction evidence is presented to support a two step thiophosphorylation process, involving initial condensation of thiophosphate to thiopyrophosphate followed by reaction of the nucleoside with the thiopyrophosphate leading to the formation of the 0-phosphorothioates. The formed (^-phosphorothioates undergo further reaction to thymidine 3'(5') -monophosphates. Dithiophosphate reacts smoothly at room temperature w ith the nucleosides, thymidine and 2 '-deoxycytidine to yield the corresponding 3 '- and 5'-0-phosphorothioate esters in a 2:3 ratio and an overall 50-65:1 yield. Thiophosphorylation of 0²:2'-anhydro-l-[beta]-D-arabinosylcytosine with dithiophosphate or thiophosphate gives three products; 0²:2 '-anhydro-l-[beta]-arabinosylcytosine 5'-0-phosphorothioate (36a), 0²:2'-anhydro-l-[beta]-D-arabinosylcytosine 3'-0-phosphorothioate (36b) and 2'-thio -2'-deoxy- cytidine 2':3'-phosphorothioate (39). | en |
dc.format.extent | 145 leaves | en |
dc.format.medium | electronic | en |
dc.format.mimetype | application/pdf | |
dc.language.iso | eng | |
dc.rights | This thesis was part of a retrospective digitization project authorized by the Texas A&M University Libraries. Copyright remains vested with the author(s). It is the user's responsibility to secure permission from the copyright holder(s) for re-use of the work beyond the provision of Fair Use. | en |
dc.rights.uri | http://rightsstatements.org/vocab/InC/1.0/ | |
dc.subject | Biochemistry | en |
dc.subject.classification | 1975 Dissertation M333 | |
dc.title | Nucleoside phosphorothioates | en |
dc.type | Thesis | en |
thesis.degree.discipline | Biochemistry | en |
thesis.degree.grantor | Texas A&M University | en |
thesis.degree.name | Doctor of Philosophy | en |
thesis.degree.level | Doctoral | en |
dc.contributor.committeeMember | Gaim, C. S. | |
dc.contributor.committeeMember | Harding, K. E. | |
dc.contributor.committeeMember | Pace, C. N. | |
dc.type.genre | dissertations | en |
dc.type.material | text | en |
dc.format.digitalOrigin | reformatted digital | en |
dc.publisher.digital | Texas A&M University. Libraries |
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