ArticleJournal of the American Chemical Society2017
Production of Stealthin C Involves an S-N-Type Smiles Rearrangement.
Article in Journal of the American Chemical Society, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 11 papers.
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Who cites it
11 citing papers in PubMed, 30 citations in OpenAlex.
- Role of a FAD-dependent monooxygenase in diazo group functionalization of kinamycin inMicrobiology (Reading, England) · 2025Article
- Cofactor-independent C-C bond cleavage reactions catalyzed by the AlpJ family of oxygenases in atypical angucycline biosynthesis.Beilstein journal of organic chemistry · 2024Article
- Targeted Isolation ofACS omega · 2023Article
- O-methyltransferase-like enzyme catalyzed diazo installation in polyketide biosynthesis.Nature communications · 2023Article
- Biochemical and structural insights of multifunctional flavin-dependent monooxygenase FlsO1-catalyzed unexpected xanthone formation.Nature communications · 2022Article
- Discovery of Stealthin Derivatives and Implication of the Amidotransferase FlsN3 in the Biosynthesis of Nitrogen-Containing Fluostatins.Marine drugs · 2019Article
- The functional differentiation of the post-PKS tailoring oxygenases contributed to the chemical diversities of atypical angucyclines.Synthetic and systems biotechnology · 2018Review
- Glutamic acid is a carrier for hydrazine during the biosyntheses of fosfazinomycin and kinamycin.Nature communications · 2018Article
- Discovery of a Diazo-Forming Enzyme in Cremeomycin Biosynthesis.The Journal of organic chemistry · 2018Article
- Molecular basis of dimer formation during the biosynthesis of benzofluorene-containing atypical angucyclines.Nature communications · 2018Article
- The Mechanism of Action of (-)-Lomaiviticin A.Accounts of chemical research · 2017Article
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Authors and funding
4 authors at 1 institution in 1 country.
Funding
Abstract
The kinamycin family of aromatic polyketide natural products contains an atypical angucycline ring system substituted with a diazo group. The enzymatic chemistry involved in constructing both of these structural features has been largely unexplored. Here we report the in vivo and in vitro production of seongomycin, a shunt product from this pathway, and stealthin C, a proposed biosynthetic precursor to the kinamycins. We show that a single enzyme, the flavin-dependent monooxygenase AlpJ, can generate these metabolites from N-acetyl-l-cysteine and l-cysteine, respectively, and that the synthesis of stealthin C likely proceeds via a nonenzymatic S-N-type Smiles rearrangement. This unexpected route to stealthin C reveals a distinct approach to install aromatic amino groups in metabolites and raises questions about the intermediacy of this species in kinamycin production.
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Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.