Structure elucidation and studies relating to the synthesis of plasmalopentaene-12

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dc.contributor.authorKeyes, Robert F.en
dc.contributor.committeechairKingston, David G. I.en
dc.contributor.committeememberBell, Harold M.en
dc.contributor.committeememberDorn, Harry C.en
dc.contributor.committeememberMerola, Joseph S.en
dc.contributor.committeememberTanko, James M.en
dc.contributor.departmentChemistryen
dc.date.accessioned2014-03-14T20:12:50Zen
dc.date.adate2008-06-06en
dc.date.available2014-03-14T20:12:50Zen
dc.date.issued1992-11-20en
dc.date.rdate2008-06-06en
dc.date.sdate2008-06-06en
dc.description.abstractThe glycerol enol ether, fecapentaene-12, is a direct acting fecal mutagen that is formed in the lower portion of the gastrointestional tract by anaerobic bacteria. The biological precursor to fecapentaene-12 is a natural product of mammalian origin whose role in the etiology of colon cancer is unknown. Preliminary evidence indicated that the precursor may be a plasmalogen with an intact pentaenol ether moiety. Further structural studies by means of degradative methods and chromatographic techniques enabled the structure of the precursor to be elucidated. Based on the structure of the precursor, the name plasmalopentaene-12 was coined. Synthetic methodology was developed for obtaining synthetic plasmalopentaene12. This was necessary in order to confirm the structure and to determine the precursor's biological role. The synthetic methodology proceeded through a novel "acyl migration" which enables the highly labile pentaenol ether to be generated late in the synthesis. Model studies indicated that this was a feasible pathway. It was also determined that this methodology may be highly adaptable to the synthesis of other plasmalogens and may also provide a new synthetic route to fecapentaene-12.en
dc.description.degreePh. D.en
dc.format.extentx, 214 leavesen
dc.format.mediumBTDen
dc.format.mimetypeapplication/pdfen
dc.identifier.otheretd-06062008-171532en
dc.identifier.sourceurlhttp://scholar.lib.vt.edu/theses/available/etd-06062008-171532/en
dc.identifier.urihttp://hdl.handle.net/10919/27979en
dc.language.isoenen
dc.publisherVirginia Techen
dc.relation.haspartLD5655.V856_1992.K494.pdfen
dc.relation.isformatofOCLC# 27880760en
dc.rightsIn Copyrighten
dc.rights.urihttp://rightsstatements.org/vocab/InC/1.0/en
dc.subject.lccLD5655.V856 1992.K494en
dc.subject.lcshFeces -- Microbiologyen
dc.subject.lcshGlycene enol etheren
dc.titleStructure elucidation and studies relating to the synthesis of plasmalopentaene-12en
dc.typeDissertationen
dc.type.dcmitypeTexten
thesis.degree.disciplineChemistryen
thesis.degree.grantorVirginia Polytechnic Institute and State Universityen
thesis.degree.leveldoctoralen
thesis.degree.namePh. D.en

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