ArticleACS chemical biology2014
Reconstruction of cladoniamide biosynthesis reveals nonenzymatic routes to bisindole diversity.
Article in ACS chemical biology, 2014. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 7 papers.
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7 citing papers in PubMed, 23 citations in OpenAlex.
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- Yeast homologous recombination-based promoter engineering for the activation of silent natural product biosynthetic gene clusters.Proceedings of the National Academy of Sciences of the United States of America · 2015Article
- Expansion of bisindole biosynthetic pathways by combinatorial construction.ACS synthetic biology · 2015Article
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Authors and funding
5 authors at 1 institution in 1 country.
Funding
Abstract
Indolotryptolines are bisindole natural products isolated from microbial and eDNA sources. Here, we report the sequence of transformations that convert an indolocarbazole to the indolotryptoline cladoniamide through reconstruction of the four-enzyme cascade in E. coli. This cascade involves, first, conversion of an indolocarbozole to a C4c-C7a cis diol by ClaX1; second, N-methylation by ClaM1; third, rearrangement to the indolotryptoline scaffold by ClaX2; and fourth, installation of an O-methyl group by ClaM3. We furthermore elucidate the origins of minor cladoniamides D-G as the products of nonenzymatic, base-catalyzed opening of the succinimide ring of cladonimiades A-B. Overall, this work reveals the precarious pathway indolocarbazole-derived metabolites must traverse as they are converted into indolotryptoline products and highlights the importance of nonenzymatic chemistry in generating bisindole diversity.
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