ArticleNature communications2015
Identification of Alp1U and Lom6 as epoxy hydrolases and implications for kinamycin and lomaiviticin biosynthesis.
Article in Nature communications, 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 18 papers.
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Who cites it
18 citing papers in PubMed.
- TfOH-Promoted Cascade Reaction of Nitriles and 1,5-Enynes: An Efficient Route to Amido-Functionalized Fluorenes.The Journal of organic chemistry · 2025Article
- Role of a FAD-dependent monooxygenase in diazo group functionalization of kinamycin inMicrobiology (Reading, England) · 2025Article
- Gut microbiome-derived hydrolases-an underrated target of natural product metabolism.Frontiers in cellular and infection microbiology · 2024Review
- 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
- Flavin-enabled reductive and oxidative epoxide ring opening reactions.Nature communications · 2022Article
- α-Ketol and α-iminol rearrangements in synthetic organic and biosynthetic reactions.Beilstein journal of organic chemistry · 2021Review
- Mutation of an atypical oxirane oxyanion hole improves regioselectivity of the α/β-fold epoxide hydrolase Alp1U.The Journal of biological chemistry · 2020Article
- Article
- Understand the Specific Regio- and Enantioselectivity of Fluostatin Conjugation in the Post-Biosynthesis.Biomolecules · 2020Article
- Molecular Dynamics to Elucidate the DNA-Binding Activity of AlpZ, a Member of the Gamma-Butyrolactone Receptor Family inFrontiers in microbiology · 2020Article
- Discovery of Stealthin Derivatives and Implication of the Amidotransferase FlsN3 in the Biosynthesis of Nitrogen-Containing Fluostatins.Marine drugs · 2019Article
- Use of genome-scale models to get new insights into the marine actinomycete genus Salinispora.BMC systems biology · 2019Article
- The functional differentiation of the post-PKS tailoring oxygenases contributed to the chemical diversities of atypical angucyclines.Synthetic and systems biotechnology · 2018Review
- Molecular basis of dimer formation during the biosynthesis of benzofluorene-containing atypical angucyclines.Nature communications · 2018Article
- Fluostatins M-Q Featuring a 6-5-6-6 Ring Skeleton and High Oxidized A-Rings from Marine Streptomyces sp. PKU-MA00045.Marine drugs · 2018Article
- Heteroatom-Heteroatom Bond Formation in Natural Product Biosynthesis.Chemical reviews · 2017Review
- New insights into bacterial type II polyketide biosynthesis.F1000Research · 2017Review
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7 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
The naturally occurring diazobenzofluorenes, kinamycins, fluostatins and lomaiviticins, possess highly oxygenated A-rings, via which the last forms a dimeric pharmacophore. However, neither the A-ring transformation nor the dimerization mechanisms have been explored thus far. Here we propose a unified biosynthetic logic for the three types of antibiotics and verify one key reaction via detailed genetic and enzymatic experiments. Alp1U and Lom6 from the kinamycin and lomaiviticin biosynthesis, respectively, are shown to catalyse epoxy hydrolysis on a substrate that is obtained by chemical deacetylation of a kinamycin-pathway-derived intermediate. Thus, our study provides the first evidence for the existence of an epoxy intermediate in lomaiviticin biosynthesis. Furthermore, our results suggest that the dimerization in the lomaiviticin biosynthesis proceeds after dehydration of a product generated by Lom6.
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