VTechWorks staff will be away for the winter holidays starting Tuesday, December 24, 2024, through Wednesday, January 1, 2025, and will not be replying to requests during this time. Thank you for your patience, and happy holidays!
 

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

Simple item page
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

Files

Original bundle
Now showing 1 - 1 of 1
Thumbnail Image
Name:
LD5655.V855_1988.J667.pdf
Size:
2.59 MB
Format:
Adobe Portable Document Format
Description:
Download

Collections

Masters Theses