- Biosynthesis of Antibiotic LL-C10037α: The Steps beyond 3-Hydroxyanthranilic Acid
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The six steps from 3-hydroxyanthranilic acid to the epoxyquinol LL-C10037α, 1, produced by Streptomyces LL-C10037 have been determined by whole-cell feedings with deuterated substrates and by cell-free studies. 3-Hydroxyanthranilic acid, 2, is decarboxylated to 2-hydroxyaniline, 11, and then oxidized to 2,5-dihydroxyaniline, 8.Acetylation at nitrogen and oxidation afford acetamido-1,4-benzoquinone, 4.A crude cell-free preparation has been found to epoxidize 4 to the epoxyquinone 16 in the presence of O2 and either NaDH or NADPH.Reduction of 16 yields 1.Therelationship of this pathway to that of fungi that produce patulin via analogous intermediates from 6-methylsalicylic acid is discussed.
- Gould, Steven J.,Shen, Ben,Whittle, Yvonne G.
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p. 7932 - 7938
(2007/10/02)
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- Protium-deuterium exchange of benzo-substituted heterocycles in neutral D2O at elevated temperatures
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H-D exchange of 2-methylbenzofuran (1), 2-methylindole (2), 2-methylbenzimidazole (3), 2-methylbenzothiazole (4), and 2-methylbenzoxazole (5) has been studied in neutral D2O at elevated temperatures.While 1, 2, 3, and 4 can be specifically labelled and 4 can be perlabelled at 225 deg C, 5 undergoes facile hydrolysis in D2O at 115 deg C to 2-acetamidophenol (8) with the incorporation of deuterium into the methyl group. Key words: H-D exchange, heterocycles, D2O, elevated temperatures.
- Werstiuk, Nick Henry,Ju, Chen
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p. 812 - 815
(2007/10/02)
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