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Lazarimide A (7) differs from cladoniamide and BE-54017 by both its halogenation pattern and the oxidation of the flipped indole moiety. The biosynthesis of lazarimides can be rationalized based on the predicted function of each gene in the Lzr gene cluster (Fig. 3C). Key novel features of the proposed biosynthetic scheme include the action of the predicted oxygenase lzrG and two predicted halogenases lzrH1 and lzrH2. The cytochrome P450, lzrG, is predicted to carry out the unique indolotryptoline core hydroxylation seen on Lazarimide A (7). lzrH1 and lzrH2 are predicted to be tryptophan-5 and tryptophan-6 halogenases, respectively. This difference in regiospecificity affords the unique halogenation pattern seen in lazarimides A (7), B (6), and C (5) |
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