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

(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.

Name thesis:degree_name

Master of Science

Level thesis:degree_level

masters

Discipline thesis:degree_discipline

Chemistry

Department dc:contributor.department

Chemistry

Grantor dc:publisher

Virginia Tech

Year dc:date.issued

1988

Author dc:creator

• Jones, Vickie Lynne

Chair dc:contributor.committeechair

• Kingston, David G. I.

Committee members dc:contributor.committeemember

• Ogliaruso, Michael A.
• White, Robert H.

Statement dc:rights

• In Copyright

Licence dc:rights.uri

• http://rightsstatements.org/vocab/InC/1.0/

Language dc:language.iso

en

Dc Identifier Other

etd-08012012-040255

OAI identifier oai:identifier

oai:vtechworks.lib.vt.edu:10919/44071