Abstract
dc:description.abstractRavidomycin is a yellow antitumor antibiotic produced by Streptomyces ravidus. Ravidomycin shows strong antitumor activity against P388 lymphocytic leukemia, the colon 38 tumor, and the CD8Fl mammary tumor. It is also very active against Gram positive bacteria. Biosynthetic studies have shown that the aglycone unit comes from the folding of a polyketide chain with the vinyl unit arising from propionic acid. Since this vinyl functionality is believed to playa role in the antitumor activity of the antibiotic, it is of interest to elucidate the stereochemical selectivity in its formation from propionic acid. The synthesis of (R) and (S)-L2-²H₁ j propionate, incorporation of the labelled material, and chemical analysis of the resulting antibiotic was be used to determine the stereochemistry of formation of the vinyl side chain. It was found that propionate was incorporated with ravidomycin with stereospecific loss of the 2-(pro-R)-proton.
Degree
thesis:*- 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
- 1989
Author and committee
dc:creator, dc:contributor.*- Author dc:creator
-
- Keyes, Robert F.
- Chair dc:contributor.committeechair
-
- Kingston, David G. I.
- Committee members dc:contributor.committeemember
-
- Dorn, Harry C.
- Wolfe, James F.
Rights
dc:rights- Statement dc:rights
-
- In Copyright
- Licence dc:rights.uri
- Language dc:language.iso
- en
Identifiers
dc:identifier.*- Dc Identifier Other
- etd-08252008-162246
- OAI identifier oai:identifier
- oai:vtechworks.lib.vt.edu:10919/34759