Title page for ETD etd-08252008-162246


Type of Document Master's Thesis
Author Keyes, Robert F
URN etd-08252008-162246
Title The biosynthesis of ravidomycin
Degree Master of Science
Department Chemistry
Advisory Committee
Advisor Name Title
Kingston, David G. I. Committee Chair
Dorn, Harry C. Committee Member
Wolfe, James F. Committee Member
Keywords
  • Streptomyces
Date of Defense 1989-07-01
Availability unrestricted
Abstract

Ravidomycin 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- H 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.

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