The biosynthesis of ravidomycin

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dc.contributor.authorKeyes, Robert F.en
dc.contributor.committeechairKingston, David G. I.en
dc.contributor.committeememberDorn, Harry C.en
dc.contributor.committeememberWolfe, James F.en
dc.contributor.departmentChemistryen
dc.date.accessioned2014-03-14T20:44:10Zen
dc.date.adate2008-08-25en
dc.date.available2014-03-14T20:44:10Zen
dc.date.issued1989-07-01en
dc.date.rdate2008-08-25en
dc.date.sdate2008-08-25en
dc.description.abstractRavidomycin is a yellow antitumor antibiotic produced by Streptomyces ravidus. Ravidomycin shows strong antitumor activity against P388 lymphocytic leukemia, the colon 38 tumor, and the CD8Fl mammary tumor. It is also very active against Gram positive bacteria. Biosynthetic studies have shown that the aglycone unit comes from the folding of a polyketide chain with the vinyl unit arising from propionic acid. Since this vinyl functionality is believed to playa role in the antitumor activity of the antibiotic, it is of interest to elucidate the stereochemical selectivity in its formation from propionic acid. The synthesis of (R) and (S)-L2-²H₁ j propionate, incorporation of the labelled material, and chemical analysis of the resulting antibiotic was be used to determine the stereochemistry of formation of the vinyl side chain. It was found that propionate was incorporated with ravidomycin with stereospecific loss of the 2-(pro-R)-proton.en
dc.description.degreeMaster of Scienceen
dc.format.extentv, 72 leavesen
dc.format.mediumBTDen
dc.format.mimetypeapplication/pdfen
dc.identifier.otheretd-08252008-162246en
dc.identifier.sourceurlhttp://scholar.lib.vt.edu/theses/available/etd-08252008-162246/en
dc.identifier.urihttp://hdl.handle.net/10919/34759en
dc.language.isoenen
dc.publisherVirginia Techen
dc.relation.haspartLD5655.V855_1989.K484.pdfen
dc.relation.isformatofOCLC# 21188611en
dc.rightsIn Copyrighten
dc.rights.urihttp://rightsstatements.org/vocab/InC/1.0/en
dc.subject.lccLD5655.V855 1989.K484en
dc.subject.lcshPolycyclic aromatic hydrocarbons -- Synthesisen
dc.subject.lcshStreptomyces -- Synthesisen
dc.titleThe biosynthesis of ravidomycinen
dc.typeThesisen
dc.type.dcmitypeTexten
thesis.degree.disciplineChemistryen
thesis.degree.grantorVirginia Polytechnic Institute and State Universityen
thesis.degree.levelmastersen
thesis.degree.nameMaster of Scienceen

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