Biochemical characterization of NotB as an FAD-dependent oxidase in the biosynthesis of notoamide indole alkaloids |
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Authors: | Li Shengying Finefield Jennifer M Sunderhaus James D McAfoos Timothy J Williams Robert M Sherman David H |
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Institution: | Life Sciences Institute, University of Michigan, Ann Arbor, Michigan 48109, USA. |
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Abstract: | Notoamides produced by Aspergillus spp. bearing the bicyclo2.2.2]diazaoctane core structure with unusual structural diversity represent a compelling system to understand the biosynthesis of fungal prenylated indole alkaloids. Herein, we report the in vitro characterization of NotB, which catalyzes the indole 2,3-oxidation of notoamide E (13), leading to notoamides C (11) and D (12) through an apparent pinacol-like rearrangement. This unique enzymatic reaction with high substrate specificity, together with the information derived from precursor incorporation experiments using (13)C](2)-(15)N](2) quadruply labeled notoamide S (10), demonstrates 10 as a pivotal branching point in notoamide biosynthesis. |
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