Jones, Vickie Lynne2014-03-142014-03-141988-05-15etd-08012012-040255http://hdl.handle.net/10919/44071(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.viii, 61 leavesBTDapplication/pdfenIn CopyrightLD5655.V855 1988.J667BiosynthesisVirginiamycin -- SynthesisThesishttp://scholar.lib.vt.edu/theses/available/etd-08012012-040255/