Title page for ETD etd-08252008-162246
|Type of Document
||Keyes, Robert F
||The biosynthesis of ravidomycin
||Master of Science
|Kingston, David G. I.
|Dorn, Harry C.
|Wolfe, James F.
|Date of Defense
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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