Synthesis of Labeled 3-Hydroxyproline and Biosynthesis of the Dehydroproline Moiety of Virginiamycin M₁

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dc.contributor.authorJones, Vickie Lynneen
dc.contributor.committeechairKingston, David G. I.en
dc.contributor.committeememberOgliaruso, Michael A.en
dc.contributor.committeememberWhite, Robert H.en
dc.contributor.departmentChemistryen
dc.date.accessioned2014-03-14T21:41:56Zen
dc.date.adate2012-08-01en
dc.date.available2014-03-14T21:41:56Zen
dc.date.issued1988-05-15en
dc.date.rdate2012-08-01en
dc.date.sdate2012-08-01en
dc.description.abstract(R,S)-[Carboxyl-¹⁴C]–cis-3-hydroxyproline was synthesized from S-[carboxyl-¹⁴C] proline. The oxygen functionality at the three position was obtained by acetylation of 1,2-dehydroproline methyl ester using lead tetraacetate. Reduction of the imine with sodium borohydride gave predominately (R,S)-[caboxyl-¹⁴C]-cis-3-acetoxyproline which was hydrolyzed with hydrochloric acid and purified by ion-exchange chromatography and recrystallization. In order to determine if cis-3-hydroxyproline is a precursor for the dehydroproline moietyof virginiamycin M1, (R,S)-[carboxyl-¹⁴C]-cis-3-hydroxyproline and S-[3,4-³H] proline with a ³H/¹⁴C of 9 were fed simultaneously to a virginiamycin producing strain of Streptomyces. The resulting antibiotic had a ³H/¹⁴C ratio of 41.3. The proline portion of the antibiotic had a ratio of 19.9. Therefore, 45% of the cis-3-hydroxyproline was incorporated, and cis-3-hydroxyproline is a precursor to the dehydroproline moiety.en
dc.description.degreeMaster of Scienceen
dc.format.extentviii, 61 leavesen
dc.format.mediumBTDen
dc.format.mimetypeapplication/pdfen
dc.identifier.otheretd-08012012-040255en
dc.identifier.sourceurlhttp://scholar.lib.vt.edu/theses/available/etd-08012012-040255/en
dc.identifier.urihttp://hdl.handle.net/10919/44071en
dc.language.isoenen
dc.publisherVirginia Techen
dc.relation.haspartLD5655.V855_1988.J667.pdfen
dc.relation.isformatofOCLC# 18676916en
dc.rightsIn Copyrighten
dc.rights.urihttp://rightsstatements.org/vocab/InC/1.0/en
dc.subject.lccLD5655.V855 1988.J667en
dc.subject.lcshBiosynthesisen
dc.subject.lcshVirginiamycin -- Synthesisen
dc.titleSynthesis of Labeled 3-Hydroxyproline and Biosynthesis of the Dehydroproline Moiety of Virginiamycin M₁en
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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