Synthesis of Belactosin A Analogs

dc.contributor.advisorDunlap, Normaen_US
dc.contributor.authorDawson Cole, Kara Anneen_US
dc.contributor.committeememberHandy, Scotten_US
dc.contributor.committeememberFriedli, Andrienneen_US
dc.contributor.committeememberVan Patten, Gregen_US
dc.contributor.departmentChemistryen_US
dc.date.accessioned2014-08-28T18:34:09Z
dc.date.available2014-08-28T18:34:09Z
dc.date.issued2014-06-20en_US
dc.description.abstractThere is continuing interest in new research on cancer as well as new cancer drugs. Belactosin A, discovered in 1999, is a naturally occurring 26S proteasome inhibitor with anti-tumor activity. The 26S proteasome is a novel anti-tumor target with only two inhibitors on the market. The structure of belactosin A contains a cyclopropyl amine linked to a A-lactone. While several syntheses have been reported, only a few analogs have been prepared and analogs are needed since belactosin A is toxic.en_US
dc.description.abstractApproaches to the synthesis of alanine cyclopropyl analogs as well as the synthesis of a simple beta-lactone are reported here. The synthetic route included a nitrocyclopropanation as well as a transfer hydrogenation to afford the core cyclopropyl amine of the analogs. Issues regarding the type of protecting group used on the "left side" of the analogs as well as attempts toward the removal of the ketone have been investigated. Attempts to couple the monoamine to the beta-lactone as well as the stability of the beta-lactone have been studied as well.en_US
dc.description.degreeM.S.en_US
dc.identifier.urihttp://jewlscholar.mtsu.edu/handle/mtsu/4270
dc.publisherMiddle Tennessee State Universityen_US
dc.subjectBelactosin Aen_US
dc.subjectNitrocyclopropanationen_US
dc.subjectPeptidomimeticsen_US
dc.subjectSynthesisen_US
dc.subject.umiChemistryen_US
dc.thesis.degreegrantorMiddle Tennessee State Universityen_US
dc.thesis.degreelevelMastersen_US
dc.titleSynthesis of Belactosin A Analogsen_US
dc.typeThesisen_US

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