Studies on advanced intermediates in the biosynthesis of streptonigrin Public Deposited

http://ir.library.oregonstate.edu/concern/graduate_thesis_or_dissertations/ng451m777

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  • Early studies on the biosynthesis of the quinoline quinone portion of streptonigrin, 1, had suggested the intermediacy of novel aromatic amino acids. In order to test this hypothesis, a series of compounds was synthesized and tested for potential incorporation. [4-¹⁵N] 4-Aminoanthranilic acid, 4 5 a , [4-² H] 7-aminoquinaldinic acid, 51 a , and [4-²H] 7-amino-5- hydroxyquinaldinic acid, 53a, were synthesized and fed to fermentations of Streptomyces flocculus. Incorporation of 45a and 51a but not 53a provided suggestive evidence that 4-aminoanthranilic acid is a new product of the shikimate pathway and provided an example of a fundamentally new route for the biological formation of the quinoline ring system. Several possibilities also existed with regard to the source and timing of the oxygenation of the A and D rings of 1. A fermentation in the presence of ¹⁸0 ₂ gas revealed that molecular oxygen was the source of all the A and D ring oxygen atoms and, along with the above results, suggested that these oxidations occur at a late stage in the biosynthesis.
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