(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. / Master of Science
Identifer | oai:union.ndltd.org:VTETD/oai:vtechworks.lib.vt.edu:10919/44071 |
Date | 01 August 2012 |
Creators | Jones, Vickie Lynne |
Contributors | Chemistry, Kingston, David G. I., Ogliaruso, Michael A., White, Robert H. |
Publisher | Virginia Tech |
Source Sets | Virginia Tech Theses and Dissertation |
Language | English |
Detected Language | English |
Type | Thesis, Text |
Format | viii, 61 leaves, BTD, application/pdf, application/pdf |
Rights | In Copyright, http://rightsstatements.org/vocab/InC/1.0/ |
Relation | OCLC# 18676916, LD5655.V855_1988.J667.pdf |
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