Studies of the biosynthesis of Sarubicin A Public Deposited

http://ir.library.oregonstate.edu/concern/graduate_thesis_or_dissertations/2514np48n

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  • Early studies on the biosynthesis of Sarubicin A, 1, had suggested the intermediacy of the novel aromatic amino acid 6-hydroxyanthranilic acid, 17. To investigate the biosynthetic steps beyond 17, [¹³C-¹⁵N carboxamide] 6-hydroxyanthranilamide, 27a, was synthesized, and fed to fermentations of Streptomyces helicus. Incorporation of 27a into 1 provided suggestive evidence that 27 is a new product of the shikimate pathway, and provided evidence that amide formation occurs early in the biosynthetic pathway to 1. Several possibilities exist for the timing of the hydroxylation and Cglycosylation steps of the quinone ring of 1. To test the chemical viability of the potential intermediate 5- glycosyl-3,6-dihydroxyanthranilamide, 29, the model quinione 67 was synthesized and reduced. The reduction product, 68, was stable in the absence of 0₂, suggesting that the proposed C-glycoside 29 is a plausible intermediate. A model for 29 was synthesized via an ultrasound catalyzed Diels- Alder reaction between the 2,2-dimethy1-5,8-dimethoxy-1,2,3,4-tetrahydro- 4-oxoquinazoline-6-carboxaldehyde, 71, and the diene 72, to give the pyran derivative 73. However, attempts to construct the carbon skeleton of 2 9 with diene 74 were unsuccessful. Isochorismate synthase was isolated from Enterobacter aerogenes 62-1, partially purified, and incubated with chorismic acid, 19, in H₂¹⁸0 . The product, isochorismic acid, 18, was purified and found to contain ¹⁸0 at the C-2 hydroxyl, demonstrating that the enzyme-catalyzed reaction proceeds via an SN₂' or addition-elimination type of reaction.
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