Type of Document	Master's Thesis
Author	Jones, Vickie Lynne
URN	etd-08012012-040255
Title	Synthesis of labeled 3-Hydroxyproline and biosynthesis of the Dehydroproline Moiety of Virginiamycin M{u2081}
Degree	Master of Science
Department	Chemistry
Advisory Committee	Advisor Name Title Kingston, David G. I. Committee Chair Ogliaruso, Michael A. Committee Member White, Robert H. Committee Member
Keywords	Biosynthesis
Date of Defense	1988-05-15
Availability	restricted
Abstract (R,S)·[Carboxyl·4C]·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)-[caboxy1·14C]-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 moiety of virginiamycin M1, (R,S)-[carboxy1-14C ]-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.
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