Synthesis of thymidine analogs as potential anti-HIV inhibitors

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dc.contributor.advisor Neenan, John
dc.contributor.advisor Morrill, Terence
dc.contributor.advisor Craig, Paul
dc.contributor.advisor Takacs, Gerald
dc.contributor.author Qiu, Bingjing
dc.date.accessioned 2011-08-09T17:49:25Z
dc.date.available 2011-08-09T17:49:25Z
dc.date.issued 1998-04
dc.identifier.uri http://hdl.handle.net/1850/13947
dc.description.abstract Acquired immunodificiency syndrome ( AIDS ) disease is caused by Human Immunodeficiency Virus (HIV). HIV is a retrovirus that uses reverse transcriptase ( RT ) to transcribe and translate its genetic information. Drugs including 3'-azido-3'- deoxythymidine (AZT) have been targeted at the polymerase domain of reverse transcriptase but not the ribonuclease H (RNase H) domain. Unfortunately, the lack of specificity of these drugs to the targeted enzyme has caused unavoidable side effects, which lead us to the design of active-site-directed irreversible enzyme inhibitors of both the polymerase and RNase H domains. Two thymidine analogs 5'-p-fluorosulfonylbenzamidothymidine ( 5 ) and 3'-pfluorosulfonyl- benzamidothymidine ( 10 ) with a terminal fluorosulfonylbenzamido group were synthesized and characterized. Of these two compounds, 3'-p-fluorosulfonylbenzamidothymidine has never been made before, while neither of these two compounds has been tested for its anti-HIV activity. Computational chemistry results were also presented showing the metal binding site of polymerase and RNase H domains of reverse transcriptase. Cysl81 and His539 were found at the above two domains, respectively. These two amino acids may serve as potential nucleophiles for affinity labeling by our inhibitors. en_US
dc.language.iso en_US en_US
dc.subject Chemistry en_US
dc.subject.lcc QR201.A37 Q58 1998
dc.subject.lcsh HIV (Viruses)--Research en_US
dc.subject.lcsh Thymidine en_US
dc.title Synthesis of thymidine analogs as potential anti-HIV inhibitors en_US
dc.type Thesis en_US
dc.description.college College of Science en_US
dc.description.department Department of Chemistry en_US

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